Islamorada Vacation Rentals

The Islamorada Village of Islands is situated between the saltwater wilderness of Everglades National Park in one direction and North America’s only coral barrier reef and the deep blue waters of the Florida Straits in the other. Owner Direct Vacation Rental has accommodations ranging from villas, to apartment rentals and condo rentals to satisfy all of your lodging needs.

Various vacation rental accommodations of either villa rentals or apartment rentals are located on one of the six islands that make up Islamorada. Stay in accommodation vacation rentals on the island of Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key. Accommodation of an apartment rental or villa rental can also be found on the offshore islands of Indian Key and Lignumvitae Key. Whichever island you choose you can be assured your accommodations will be first class.

The Islamorada area might be the only place on earth where it is possible to leave either your apartment rentals or villa rentals to catch a sailfish in the morning, and then venture into the backcountry in pursuit of bonefish, permit, tarpon, snook and redfish in just inches of water in the afternoon. With a fleet of highly skilled professional recreational fishing captains, Islamorada’s reputation as The Sport Fishing Capital of the World is well deserved.

Of course from vacation rentals there is much more to experience here in Islamorada then fishing. At Long Key State Park meander along lush, tropical nature trails. AtWindley Key Fossil Reef Geological State Park view an old quarry dug by the late Henry Flager’s railroad workers. At Lignumvitae Key Botanical State Park glimpse into Florida’s unique Island history dating back to the early 1800’s.

A trip to Islamorada would not be complete without sampling some of the local island cuisine headlined by succulent fresh seafood served everywhere from island tiki bars and dockside fish houses to gourmet beachfront cafes and secluded island bistros. All of which are located close to a number of villa rentals that are available. Shoppers will also be able to step out from their vacation rentals to enjoy many area boutiques and galleries filled with one-of-kind gifts, apparel and art.

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  • Islamorada Luxury Condo with 50' Private Boat Slip

    Islamorada Luxury Condo

    Islamorada: Bay Harbour: Condo in a gated community
    • 2 BDR
    • 3 BA
    • Sleeps 6
    • #209708
    $243 to $343 USD/night Paypal
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbeque grills, tennis equipment, beach chairs and coolers. This spectacular condo offers two master bedrooms with private full bathrooms, additional half bath and full size washer and dryer. Additionally, each bedroom and the living room has flat screen televisions with cable tv. A dvd player is included in the living room. There is free wifi and telephone included for your use. The kitchen has stainless steel appliances, granite countertops and everything you need to prepare and serve a gourmet meal. The large balcony overlooking the water offers plenty of seating. Enjoy a meal or coffee while you take in the expansive views or enjoy the sunrise. Additionally, you will have a direct view of your boat parked in a private boat slip just steps away. Located at mile marker 75, this boater’s paradise is just minutes from fishing in the gulf or ocean, diving or snorkeling beautiful reefs, jet skiing, parasailing, kiteboarding or kayaking. Call to book your vacation of a lifetime.
  • Executive Bay 2 / 1.5 - Great Location. Great Unit!

    Executive Bay 2 / 1.5

    Islamorada: Executive Bay Club: Townhouse in a gated community
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #234599
    $164 to $171 USD/night Paypal
    Come to Paradise and Enjoy it with Comfort. Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your own Dock and incredible sunsets. Our Two Story Unit is nicely decorated and furnished, Granite Kitchen counter tops, stainless steel appliances , complete with everything you need. Large Living Room and Dining Room with large flat panel LCD TV , and Outside Patio with a relaxing atmosphere. Master Bedroom (Queen Size Bed) plus a Loft, Second Bedroom Has 2 Twin Size Beds, Half Bathroom on the first floor. This unit is in a great location, across the pool, clubhouse and steps to the beach and fishing pier.
  • With a Separate Downstairs

    With a Separate Downstairs

    Islamorada: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 8
    • #241192
    $239 to $655 USD/night  
    With a separate downstairs apartment, this 4BR/3BA waterside home is perfect for group getaways. Cool off in the pool, soak in the hot tub, or fire up the BBQ. You’re a quick drive to the Holiday Isles Tiki Bar, Theater of the Seas, and more. Sleeps 8.. After a sun-soaked day, head back to your canal-front 4BR/3BA home and take a refreshing dip in the sparkling private pool. Fire up the BBQ for an al fresco feast on the covered patio. As the stars come out, go for a soak in the private hot tub. A full wraparound balcony, cool tile floors, and bright coastal décor all add up to the perfect Florida vacation home. With a separate downstairs apartment, this space is perfect for a large family or a group of up to four couples. Located right on the canal, your rental is in the heart of Islamorada. Spend the day boating or fishing in the sport fishing capital of the world. You’re also just a quick drive to the Tiki Bar at Holiday Isles, Theater of the Seas, and more. ABOUT THE HOME Stretch out on the leather sectional sofa in the welcoming living area and catch a movie on the 50” flat screen TV. Head out to the screened patio to enjoy fantastic water views. Gather at the eight-person table for a festive card game. The bistro table with two chairs is an ideal spot for your morning coffee, and the barbeque grill offers an option for at-home lunches. The kitchen features beautiful updates, including granite counters and stainless steel appliances. Grab one of three seats at the bar for appetizers, then gather at the six-person dining table for a home-cooked meal. At the end of a fun-filled day, the master bedroom beckons with plush a king bed, 46” flat screen TV, and an en-suite bathroom with a tub/shower combination. The second bedroom offers a king bed and 40” flat screen TV, while the third bedroom features a comfy queen bed. The adjacent guest bathroom has a tub/shower combination. A separate apartment on the ground level makes a perfect in-law suite or children’s retreat. The space includes a living room with sofa and 32” flat screen TV, as well as a kitchenette with granite counters and a refrigerator, sink, hot plate, microwave, and a bar seating for two. The bedroom features a queen bed and a sliding glass door with access to the pool deck. The updated bathroom has a walk-in shower. Guest amenities include complimentary Wi-Fi and a washer/dryer. Parking is provided for up to five vehicles (including one covered parking spot). THE LOCATION This home commands a prime location in the heart of Islamorada, in an upscale neighborhood of waterfront homes. You’re just 2 miles from the Tiki Bar at Holiday Isles—known for it good eats and rum-runner cocktail. Sit by the beach or check out the live entertainment. Other nearby restaurants include Smuggler’s Cove Resort, Wahoo’s Bar & Grill Restaurant, and Marker 88. All are within 2.5 miles. If you’ve ever dreamed of swimming with dolphins, now’s your chance. Theater of the Sea (2 miles) features an array of animal shows, snorkeling, and dolphin encounters. Want to explore further afield. You’re within a 2-hour drive of both Miami and Key West. Take a day trip and be home in time to watch the sunset.
  • Kick off your Sandals

    Kick off your Sandals

    Islamorada: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #238432
    $143 to $205 USD/night Credit Card Pet Friendly
    Kick off your sandals and get into full vacation mode—this 2BR/2BA Islamorada house is the ideal home base for your relaxing getaway. Enjoy a quiet private beach. Walk to restaurants and bars. Sleeps 6.. Straight from the pages of a travel magazine, this 2BR/2BA Islamorada house commands a prime location overlooking the jewel-toned waters and white sands. Inside, bright sunshine comes in through multiple sliding glass doors, bathing the open spaces in natural light. Start and end your day out on the screened balcony. When it’s time for a night out, you’re just a short walk from great restaurants and bars. The heart of Islamorada is just 8 miles away. The area is also known for outstanding snorkeling and scuba diving. ABOUT THE HOUSE Take in the panoramic views from the screened balcony that spans the front of the house. Curl up with a book on the patio couch, and dine al fresco at the four-person table, enjoying warm breezes and the sound of the waves. Tasteful beach decor and neutral colors create an inviting ambiance in the living room. Settle into the couch to watch the 39” flat screen TV, or just kick back and enjoy beautiful ocean views through the sliding glass doors. Pack lunches for the beach and make inspired dinners in the well-equipped kitchen. Sit down to meals around the dining table for four. Two bedrooms sleep six comfortably. Slumber in the master bedroom’s king bed, and enjoy plenty of storage in the walk-in closet and several dressers. Take in the water views through the sliding glass doors. An en-suite bathroom offers a tub/shower combination. Guests will love the views from the second bedroom, featuring two full beds, a large closet, and sliding glass doors out to the balcony. The en-suite bathroom has a tub and shower combination. There’s parking underneath the home for one car with additional two spots in the driveway. Other amenities include an outdoor shower and a laundry room with washer/dryer. THE LOCATION Known as the “Village of Islands,” Islamorada (8 miles away) is brimming with natural beauty and lots to see and do. Get up close and personal with dolphins at the Theater of the Sea, browse the exhibits at the History of Diving Museum, and explore the Windley Key Fossil Reef Geological State Park. The area offers exceptional scuba diving and snorkeling, which you can do on your own or hire a professional guide for a tour. The Caloosa Cove Resort is a 15-minute walk away and has a full-service marina and island store. Treat yourself to dinner out at one of the nearby restaurants. Local favorites include Habanos, which offers oceanfront dining, and the Safari Lounge for an after-dinner nightcap.
  • This 3br/2ba Penthouse Condo

    This 3br/2ba Penthouse

    Islamorada: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #239702
    $187 to $435 USD/night  
    This 3BR/2BA penthouse condo features a screened balcony with breathtaking water views. The ocean is just across the street and the coral reef is just minutes away. Enjoy Bay Harbour’s tennis courts, deep water boat slips, spa, and sparkling pool. Sleeps 8. This 3BR/2BA penthouse condo features a gourmet kitchen and a screened balcony with breathtaking water views. The ocean is just across the street and the coral reef is just minutes away. Cool tile floors and an inviting upscale décor make this an ideal Florida Keys getaway for a pair of families or group of friends. As a guest at Bay Harbour, you can enjoy an array of amenities, including tennis courts, clubhouse with fitness room, deep water boat slips in a protected harbor, BBQ area, and a sparkling pool and spa. ABOUT THE HOME After a day of fishing, boating, or exploring the Keys, come home to your third-floor penthouse condo and enjoy a glass of wine on your private screened balcony. There’s comfortable seating for five and breathtaking ocean views. As evening falls, head up to the rooftop balcony for star gazing. The kitchen is spacious and open to the dining room. You’ll find everything you need, including a full suite of stainless steel appliances, a wine fridge, and a Wolf gas range. When it’s time to each, there’s room for two at the bar, and six people can gather at the custom wood dining table. After dinner, retreat to the living area, where you can stretch out on the large sectional sofa and armchairs. Plan out tomorrow’s adventures or relax with a film on the 60” flat screen TV. The master bedroom features a king-size bed, 26” flat screen TV, and door to the balcony. The en-suite bathroom has a dual vanity, a bidet, and a walk-in shower with twin shower heads. There are two guest bedrooms, one with a king and another with two queens. The nearby guest bathroom features a jetted tub. Guest amenities at this home include complimentary Wi-Fi. Guest parking is available in front of the building. THE LOCATION Located in the Bay Harbour community, this condo offers access to an array of amenities, including tennis courts, a clubhouse with fitness center, and deep water boat slips in a protected harbor. Relax by the sparkling pool on one of the lounge chairs, or soak in the relaxing spa. For a fun al fresco meal, take advantage of the BBQ and picnic area. You’re just across the street from the ocean. Spend the day on the water fishing for big game or head to the back country in search of snook or tarpon. For snorkelers and scuba divers, the coral reef is just minutes away. For a meal out, try Habanos Oceanfront Dining for Cuban fare or the Safari Lounge for a fun atmosphere with seafood and live music. Both are less than a mile up the road.
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  • On the Ocean in Key West

    On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #69125
    $245 to $405 USD/night Credit Card
    1350sq. ft. of fabulous living space located in a ocean front condo on the 2nd floor. Garden and partial ocean view from a 38ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. The property is decorated and managed / maintained by me personally assuring you of a memorable vacation in a property that is way above the average investor owned rentals offered by management companies. The average temperature is 77.8 degrees, making Key West the warmest city (average temperature) in the United States. It has never been below 41 or above 98 degrees.
  • Moon Bay Yacht and Tennis Club

    Moon Bay Yacht and Tennis

    Key Largo: Moon Bay Yacht and Tennis Club: Condo in a complex
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #13373
    $128 to $228 USD/night Credit Card
    This beautiful condo is on the fourth floor. There is an elevator in the building. Being on the fourth floor makes for a spectacular view from the screened in porch, living room, dining room, and master bedroom. Ceiling fans. Moon Bay has everything you need for a great vacation. There are free tennis courts, pool, saunas, a private boat slip,basketball hoop, and a dock for fishing and swimming to mention just a few of the amenities. There is a recreation room with ping pong and a water front grill. Wireless Internet.
  • This Inviting 2br/2ba Condo

    This Inviting 2br/2ba

    Tavernier: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #241805
    $139 to $341 USD/night  
    This inviting 2BR/2BA condo is located in the beachfront Ocean Pointe at Key Largo complex and features a host of amenities like a heated pool, tennis, and beach volleyball. Minutes to dining, shopping, and water activities. Sleeps 6.. Aptly named the Sunrise Suite, this east-facing 2BR/2BA Key Largo condo offers glorious morning views. Take advantage of on-site amenities at the beachfront Ocean Pointe resort, like a heated pool, a private beach with volleyball, Tiki Hut, a brand-new Boardwalk, tennis courts, and a private marina. There’s lots to do just minutes away—from restaurants and shopping to water activities like boating, snorkeling, swimming with dolphins and parasailing. You can also go scuba diving and take glass-bottom boat tours. ABOUT THE CONDO After a fun-filled day at the beach, relax in the laid-back living room with comfortable seating and a 32” flat screen TV. The sofa converts to a queen-size sleeper for extra guests. Step out to the private balcony with seating for two and take in the lush Key Largo landscape. The well-equipped kitchen has granite counters, full-size appliances, coffeemaker, toaster, and all the cookware and gadgets you’ll need to create tasty home-cooked meals. A spacious breakfast bar seats five. Between the two bedrooms and sleeper sofa in the living room, this condo sleeps six. A good night’s sleep awaits you in the master bedroom, which has a king bed with crisp white bedding, tropical touches, a 32” flat screen TV, and a large closet complete with a safe. The en-suite bathroom features a big jetted soaking tub/shower combination. Across the hall, the second bedroom has a queen bed and lots of storage in the closet and dresser. The en-suite bath comes with a tub/shower combination and can also be accessed from the hallway. Extra perks include a washer/dryer and complimentary Wi-Fi. Unassigned parking is provided for two cars in the outdoor lot. THE LOCATION As part of the gated Ocean Pointe Resort, the condo features a host of amenities. Soak up the sun from a poolside lounger by the resort-style pool. Stay active on the tennis and beach volleyball courts. Or bring your bait and tackle to the fishing pier. Other Ocean Pointe amenities include a cafe, cocktail bar, private marina with boat slips, and a private beach with thatched tiki huts. You’ll also benefit from the condo’s prime location, just minutes from shopping and dining. Whether you’re looking for something low-key or want an adrenaline rush, you’ll find it close by. Water sports abound, including boating, sailing, fishing, snorkeling, and parasailing. Go on an Everglades eco-tour, view amazing sea life aboard a glass-bottom boat, rent jet skis, or swim with dolphins—you can do it all here. Scuba divers will love exploring Molasses Reef, just 7.6 miles from the resort marina.
  • Escape to this 2br

    Escape to this 2br

    Marathon: Vacation Rental
    • 2 BDR
    • 1 BA
    • Sleeps 6
    • #241101
    $221 to $497 USD/night  
    Escape to this 2BR Duck Key villa boasting two balconies overlooking the aquamarine water. Your two-story end unit features lots of natural light and privacy. Easily access a marina, Hawks Cay Resort restaurants, and an array of island excursions. Sleeps 6. PROPERTY OVERVIEW Escape to this 2BR/1.5BA Duck Key villa boasting two balconies overlooking the aquamarine water. Your two-story end unit features nautical-inspired design elements paired with lots of natural light and privacy. Easily access nearby fishing charters, boat rentals, diving, Dolphin Connection and Hawks Cay Resort restaurants on the 568-acre island. LIVING AREA Sprawl out on the queen-size sleeper sofa in the living room and enjoy a movie on the 42” flat screen TV. An additional armchair offers a relaxing seat with waterfront views. KITCHEN & DINING Granite countertops and stainless-steel appliances shine in the well-equipped kitchen. Sip morning coffee at the breakfast bar, and share meals at a dining table that accommodates four. BEDROOMS & BATHS This condo includes two bedrooms that sleep six total. One full bath and a half bath are each stocked with a complimentary starter supply of toiletries. Upstairs, the master bedroom is outfitted with a queen-size bed, 26” flat screen TV, and closet. Wake up and breathe the fresh ocean air from your private second-story balcony overlooking the aquamarine water. Two twin-size beds are found in the second bedroom, as well as a 26” TV, and a closet. Both bedrooms share a bath with a tub/shower combination. The half bath is located on the main floor. OUTDOOR AREA Sliding glass doors open to a private balcony complete with a bistro table, four chairs, and a ceiling fan for warm evenings. Enjoy direct ocean access via a short walk from your private outdoor space. The master bedroom includes a second-story balcony overlooking the clear water. EXTRA AMENITIES Although this privately-owned villa is not affiliated with the Hawks Cay Resort, you can take advantage of the resort’s restaurants and excursions. Unassigned parking is available for two vehicles in the parking lot. A washer/dryer and complimentary Wi-Fi are provided. LOCATION Nearby you'll find fishing charters, boat, kayak, and stand-up paddleboard rentals, snorkeling trips, and sunset cruises. Or hop onto a jet ski for a high-speed ocean adventure. Hop in the car and explore the awe-inspiring Seven Mile Bridge; go fishing or kayak around Curry Hammock State Park. Check out the Dolphin Research Center where you can learn about the marine ecosystem and swim with dolphins. At sunset, head over to the Marina to pick up the catch of the day from fishermen and dine on home-cooked fresh fish. Make reservations at the resort’s main restaurant, Ocean for local seafood or enjoy casual fare at Coral Grill. Upon arrival, easily access your villa with a keyless secure door code; no need for an in-person key exchange. Your rental will be professionally cleaned and ready for you to enjoy. You can expect all comforts of a fine hotel, including shampoo, soaps, paper products, towels, and linens. Your home will include a HomeDroid tablet (electronic guest directory) providing specific home details, local suggestions, Wi-Fi access, TV instructions, and more. If you need anything at all before, during, or after your stay, our 24/7 local team is always ready to help!
  • Fishing and Boating are

    Fishing and Boating are

    Marathon: Vacation Rental
    • 2 BDR
    • 1 BA
    • Sleeps 6
    • #238549
    $156 to $485 USD/night Credit Card
    Fishing and boating are part of everyday life at this 2BR/1.5BA Marathon home with private docks, balconies, and bikes. Tucked into a cove in Boot Key Harbor, the home offers ocean access and close proximity to shopping, dining, and nightlife.. Fishing and boating are part of everyday life at this 2BR/1.5BA Marathon home for six guests with ocean access. Tucked into a cove in Boot Key Harbor, the home offers peaceful waterfront living and two breezy balconies. Fire up the grill to prepare a family barbecue, and come together in the backyard dining area. Launch a boat from one of the two private docks, and spend a day cruising in Boot Key Harbor. Hop on seven complimentary bikes and pedal around the neighborhood, or walk 5 minutes to shopping, dining, and nightlife. ABOUT THE HOUSE After relaxing days at the beach, return home to your two-story, waterfront home to whip up a recipe in the fully equipped kitchen with countertop seating for four. The sun-soaked living area is a perfect spot for socializing—with water views framed in a wall of windows, you’ll be rushing to the balcony for a closer look. In the evenings, pick a seat from among the leather sleeper sofa, love seat, and armchair, and settle in for a movie on the 34” flat screen TV. Step out onto the covered balcony with ceiling fans and unwind in the sitting area with four chairs. Light up the grill for a family barbecue, and descend the stairs to the backyard dining area and dock. Upstairs, retreat to two comfortable bedrooms, which share a guest bathroom with tub/shower combination. The king-size master bedroom features a 28” flat screen TV and mirrored closet. Sliding glass doors lead to a private master balcony with seating for two. The second bedroom offers two twin beds and a writing desk—ideal for catching up on emails. Amenities include WiFi, a washer/dryer set, beach essentials, seven bicycles, and parking for six cars. A half bath is just off the living area. The docks can accommodate a boat up to 75' and there is parking for two boat trailers, two boats and two trucks. THE LOCATION Fishing and boating are part of everyday life at this waterfront home in Marathon. Launch a boat from one of the two private docks perched on the cove, and spend quiet mornings cruising through Boot Key Harbor. Take a seat on your upper balcony and watch for glimpses of marine life—you might spot manatees. Hop on one of the seven complimentary bicycles and pedal around the neighborhood. When you’re ready for a night on the town, stroll to an array of bars and restaurants within a half mile of your door.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #241322
    $251 to $601 USD/night  
    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and hotel-quality towels and linens. And we make it easy to stay with us. Drive straight to your rental and access the rental with a unique lock code that we give only to you. When you book, we will send you our mobile app with directions, lock code, and instructions. We’re available 24 hours a day with live help. All vacation rentals follow local and state tax rules. Each reservation includes applicable taxes, a cleaning fee, and a Property Damage Protection policy.
  • Launch a Boat Or

    Launch a Boat Or

    Marathon: Vacation Rental
    • 2 BDR
    • 1 BA
    • Sleeps 6
    • #238552
    $171 to $485 USD/night Credit Card
    Launch a boat or cast a reel from this 2BR/1.5BA Marathon duplex home with two private docks, two waterfront balconies, and bikes. Situated on a cove in Boot Key Harbor, enjoy backyard dining and leisurely strolls to nearby dining and nightlife. Sleeps 6.. Waterfront living awaits at this 2BR/1.5BA Marathon duplex home for six guests. This is a fisherman's dream with a work shop area and two bait freezers; not only will fisherman enjoy the easy access to the ocean but so will divers. Situated on a beautiful cove in Boot Key Harbor, the home is equipped with two private docks with four slips. Launch a boat with easy access to the ocean. When you want to explore the area, hop on one of the seven complimentary bikes and pedal around the neighborhood, or walk 5 minutes to shopping, dining, and nightlife. ABOUT THE HOUSE This two-story waterfront vacation home offers a well-equipped kitchen with a gas range. Make a favorite recipe and savor family meals at the bar with seating for four. Sit and chat in the sunny living area with sleeper sofa and plush love seat, or watch a movie on the 32” flat screen TV. Look out at the water from your spot on the couch, or view it up close on a covered balcony with gas grill. A half bath is just off the living area. A patio table with four chairs is a lovely place to dine al fresco. After dinner, descend the stairs to the backyard and dock area, and sip evening cocktails around two additional tables with bench seating. On the second floor, the master bedroom features a queen-size bed, 19” TV, a mirrored closet, and a quiet workspace that’s perfect for catching up on emails. Step through sliding glass doors to a private master balcony with seating for two. The second bedroom has two twin beds and chest of drawers. An elegant wall mirror is ideal for getting ready in the morning. The bathroom has a tub/shower combination Amenities include Wi-Fi, washer/dryer, beach essentials, fishing freezers, seven bicycles, and parking for six cars. THE LOCATION Fishing and boating are part of everyday life at this waterfront home in Marathon. Launch a boat from one of the two private docks (with room for four boats), and spend quiet mornings cruising through Boot Key Harbor or out to the open ocean. Take a seat on the upper balcony and watch for manatees (over a dozen gather in this cove every season). Hop on one of the seven complimentary bicycles and pedal around the neighborhood. When you’re ready for a night on the town, stroll to an array bars and restaurants within a half mile of your door.
  • Newly remodeled home in

    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242079
    $549 to $749 USD/night  
    Newly remodeled home in The Florida Keys with 3 bedrooms and 3.5 bathrooms. Located within a private yacht club with boat slips available for rent as well a centrally located clubhouse and pool area complete with top-notch amenities.. Marlin Bay Yacht Club is a newly remodeled private community located within Marathon, Florida in the heart of The Florida Keys. As you drive through the elegant gates of the property you are welcomed by an exquisitely decorated 2-story clubhouse. As you enter the clubhouse you are greeted by our accommodating concierge team who is more than eager to assist you in planning a trip of a lifetime. The clubhouse features numerous amenities for you to enjoy during your stay, including a full-service bar, a state-of-the-art fitness center, a yoga studio, sauna, steam room, billiards, shuffleboard, multiple big screen TVs, and beautifully appointed lounges for you to relax and spend time with your family and friends. As you walk through the clubhouse and step outside you are immediately taken back by the incredible views that The Keys have to offer. Here you will find a lovely lagoon style pool, a relaxing whirlpool, modern lounge furniture to enjoy the warmth, and a full-service tiki bar. Beyond this remarkable resort-like atmosphere we also feature a private 99-slip marina complete with an experienced dockmaster to prepare you and your vessel for an amazing sea excursion. Even if you do not plan to boat during your time with us, the clubhouse, the pool area and the dramatic 3-story residences are certainly designed to please all guests and provide you with luxury accommodations. Our 3-bedroom homes are fully furnished, professionally decorated, and feature an open floorplan. As you enter the ground floor from your 2-car garage you will find a lovely master bedroom complete with its own full bathroom and private patio. As you ascend onto the second floor you will find a state-of the-art gourmet kitchen which seamlessly flows into modern dining and living areas. On this level you will also find another private deck overlooking the beautifully landscaped pool area and a conveniently placed half bathroom. Last but not least, as you arrive on the third floor you will discover an additional master bedroom complete with its own full bathroom, wet bar, and private balcony. The third bedroom is also located on this level with 2 twin beds and a private bathroom as well. If the multiple levels concern you, there is no need to worry as our homes include elevators so you can easily access each floor.
  • This 2br/2ba with Canal

    This 2br/2ba with Canal

    Key Largo: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 8
    • #238387
    $185 to $217 USD/night Credit Card
    This 2BR/2BA with canal access has a private dock for boats up to 35’. Savor a cocktail in the shade of the backyard tiki hut, and soak in the hot tub while watching a movie on one of two flat screen TVs. Bonus bedroom in the finished garage.. Make the most of the Key Largo sunshine in the home’s outdoor oasis. You’ll feel cool and comfortable on the warmest summer days with a misting system that provides invigorating refreshment and controls mosquitos. Relax with friends under the shaded tiki hut or unwind with a soak in the hot tub. Mixologists, try your hand at new cocktails in the beach-themed outdoor bar. With two flat screen TVs, you can watch films from the hot tub or the bar. A private dock with access to the Gulf accommodates boats up to 35’. A high-tech boat lift with remote control makes raising, lowering, and storing your boat a breeze. ABOUT THE HOUSE The second-floor living room, kitchen, and dining area are bright and comfortable. The living room has a leather sectional with seating for four, a perfect spot to put your feet up and catch a movie on the 51” TV. Just outside your door, a private outdoor oasis awaits. Beach-lovers will adore the tiki hut, with a sitting area, hot tub, and two flat screen TVs. Barbecue on the propane grill and dine at the outdoor dining table, then cap your evening with a refreshing cocktail prepared at the outdoor bar. Or make meals in the well-equipped kitchen to enjoy at the dining area for four. After dinner, step out onto the balcony to enjoy views of beautiful Key Largo. The second-floor master bedroom is a welcoming retreat with a queen bed, walk-in closet, and 41” TV. A bathroom with walk-in shower is conveniently located adjacent. On the first floor, the guest bedroom sleeps three with a twin-over-full bunk bed. An en-suite bathroom and 31” TV make this a private hideaway perfect for kids. For larger groups, a bonus bedroom in the finished garage sleeps an extra three guests on a twin inflatable mattress and full-size Murphy bed. Amenities include a washer/dryer in the garage. There is ample driveway parking for four cars. For fishing enthusiasts, a freezer in the garage keeps your catch fresh. THE LOCATION This Key Largo home is perfect for sailors, equipped with a dock for boats up to 35’ and a remote-controlled boat lift. The open waters of the Gulf of Mexico are a short sail away. View underwater sights while snorkeling at John Pennekamp Coral Reef State Park, less than a 10-minute drive from your door. Paddle or kayak through the Everglades for a true Key Largo experience.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241323
    $251 to $601 USD/night  
    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and hotel-quality towels and linens. And we make it easy to stay with us. Drive straight to your rental and access the rental with a unique lock code that we give only to you. When you book, we will send you our mobile app with directions, lock code, and instructions. We’re available 24 hours a day with live help. All vacation rentals follow local and state tax rules. Each reservation includes applicable taxes, a cleaning fee, and a Property Damage Protection policy.
  • Located in Old Town

    Located in Old Town

    Key West: Vacation Rental
    • 1 BDR
    • 1 BA
    • Sleeps 3
    • #238465
    $88 to $146 USD/night Credit Card
    Located in Old Town, this restored 1920s conch house apartment is classic Key West. Near Duval Street, beaches, and the historic seaport. Just a short walk to dining and shopping. Enjoy access to a heated pool. Sleeps 3.. Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This light-filled, open-concept apartment has vaulted ceilings and inviting relaxation spaces. Enjoy a movie in the comfy living room, with a queen-size sleeper sofa and 37” flat screen TV. Cook your meals in the well-equipped kitchen, with a convenient island with seating for two. The bright dining space accommodates four. Take a dip in the shared heated pool, or sit out on a private porch and enjoy the cool shade provided by the surrounding palm trees. A bubbling fountain in the front yard welcomes you to the property. The bedroom has a plush queen-size bed and a full bath. Amenities include a washer/dryer. And there is open street parking available for one vehicle. THE LOCATION A plethora of local attractions are nearby. Southernmost Point and the Ernest Hemingway museum are both an 8-minute drive from the house, while famed Duval Street is less than a mile away. There are plenty of walkable restaurants, shops, and attractions on Fleming Street, so you never have to go far to have a great time.
  • Newly remodeled home in

    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242078
    $549 to $749 USD/night  
    Newly remodeled home in The Florida Keys with 3 bedrooms and 3.5 bathrooms. Located within a private yacht club with boat slips available for rent as well a centrally located clubhouse and pool area complete with top-notch amenities.. Marlin Bay Yacht Club is a newly remodeled private community located within Marathon, Florida in the heart of The Florida Keys. As you drive through the elegant gates of the property you are welcomed by an exquisitely decorated 2-story clubhouse. As you enter the clubhouse you are greeted by our accommodating concierge team who is more than eager to assist you in planning a trip of a lifetime. The clubhouse features numerous amenities for you to enjoy during your stay, including a full-service bar, a state-of-the-art fitness center, a yoga studio, sauna, steam room, billiards, shuffleboard, multiple big screen TVs, and beautifully appointed lounges for you to relax and spend time with your family and friends. As you walk through the clubhouse and step outside you are immediately taken back by the incredible views that The Keys have to offer. Here you will find a lovely lagoon style pool, a relaxing whirlpool, modern lounge furniture to enjoy the warmth, and a full-service tiki bar. Beyond this remarkable resort-like atmosphere we also feature a private 99-slip marina complete with an experienced dockmaster to prepare you and your vessel for an amazing sea excursion. Even if you do not plan to boat during your time with us, the clubhouse, the pool area and the dramatic 3-story residences are certainly designed to please all guests and provide you with luxury accommodations. Our 3-bedroom homes are fully furnished, professionally decorated, and feature an open floorplan. As you enter the ground floor from your 2-car garage you will find a lovely master bedroom complete with its own full bathroom and private patio. As you ascend onto the second floor you will find a state-of the-art gourmet kitchen which seamlessly flows into modern dining and living areas. On this level you will also find another private deck overlooking the beautifully landscaped pool area and a conveniently placed half bathroom. Last but not least, as you arrive on the third floor you will discover an additional master bedroom complete with its own full bathroom, wet bar, and private balcony. The third bedroom is also located on this level with 2 twin beds and a private bathroom as well. If the multiple levels concern you, there is no need to worry as our homes include elevators so you can easily access each floor.
  • Soak in Water Views

    Soak in Water Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #238859
    $179 to $393 USD/night Credit Card
    Soak in water views on the sun-kissed rooftop terrace of this 3BR/3BA home. Enjoy a master suite oasis with luxurious jetted tub and private deck. Keep your boat at your fingertips with plenty of dock space for rent nearby. Sleeps 8.. Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat nearby at one of the many spots available for rent, and then stroll back to the house to rest and recharge. You’ll feel on top of the world as you gaze over the clear waters of Florida Bay from the comfort of your 700-square-foot rooftop terrace, furnished with plenty of comfortable chairs, sofas, and recliners. End your day in the tranquil master suite. After a glass of wine or a nightcap on your private balcony, enjoy a soak in the jetted tub or a movie on the flat screen TV. ABOUT THE HOUSE For the ultimate movie night, gather your group in the spacious living area on the second floor and play your favorite films on the 55” flat screen TV. A sofa and love seat offer seating for five. Discerning chefs will appreciate the kitchen’s stainless steel GE appliances and dishwasher. Enjoy meals at the dining table for six or on the balcony with views of the neighborhood. Unwind in the first-floor master suite with a queen bed, walk-in closet, and 40” TV. The en-suite bath will be your oasis; rinse off in the walk-in shower or soak in the jetted tub. The private deck with a bistro set is perfect for enjoying coffee or a romantic cocktail for two. The second bedroom, located on the first floor, includes two twin beds, a 26” flat screen, and an en-suite bath. On the second level, the versatile third bedroom contains a queen bed and a queen-size futon to use as seating or sleeping accommodations for two. On the second-floor balcony, you’ll find a spiral staircase leading to your expansive private roof terrace. Lounge on recliners and soak in the sun, or gather your group in the shaded seating area to enjoy games, conversation, and panoramic bay views. Plan a barbecue on the shaded patio beneath the house, equipped with a gas grill and a dining area for eight. Two parking spaces are available, and you’ll find a washer/dryer on the first floor. THE LOCATION Take advantage of well-kept shared amenities. Lounge by the pool and enjoy sweeping bay views while you swim, or head down to the docks, where boat owners can rent bayside space to store their vessel. Idyllic Sunset Park Beach is just a 5-minute drive from your door. Florida Keys Aquarium Encounters, less than a half mile away, is perfect for a family-friendly afternoon of snorkeling and discovering marine life.
  • This 4br/3ba Key Largo

    This 4br/3ba Key Largo

    Key Largo: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 6
    • #242718
    $218 to $531 USD/night  
    This 4BR/3BA Key Largo home is a water lover’s paradise with boat slip, kayaks, and a stand-up paddleboard. Go for a dip in your private pool and hot tub, whip up a recipe in the outdoor kitchen, and gather around the backyard fire pit. Sleeps 6.. Welcome to Manatee Manor. Find paradise at this newly remodeled 2,100 square foot 4BR/3BA vacation home, set on the canal in Key Largo. With spacious interiors, an expansive backyard, and indoor/outdoor kitchen and dining areas, there’s plenty of room for six people. Spend your days poolside with a cool drink in hand. Enjoy indulgent soaks in your private hot tub, or make use of the kayaks and standup paddleboard provided. Bring along your boat and tie off at the private dock for craft up to 37’ in length. This exceptional home offers 120’ of water frontage. Watch for glimpses of marine life from your dockside palapa, or go exploring in Everglades National Park and the coral barrier reef. ABOUT THE HOME Inside, the gourmet kitchen boasts granite countertops, well-stocked cabinetry, and a full suite of stainless steel appliances. Grab a seat at the breakfast bar for four, or dine together at a sleek wood table. Mix a cocktail at the granite bar with wine fridge and ice maker, and get comfortable in the living area, furnished with a plush sectional and matching sofa and a 55” flat screen TV. Outdoors, spend quiet mornings on the canal with the kayaks or standup paddleboard provided for you. Or launch your own boat from the private dock. Prefer to lounge on land. Soak up the sun from a chaise recliner, then cool off with a dip in the custom in-ground swimming pool with spa and waterfall. When you’ve worked up an appetite, prepare a family recipe in the full outdoor kitchen, complete with a fridge, sink, stove, and gas grill. Dine at the patio table for six, then toast marshmallows at the fire pit and have s’mores for dessert. At night, drift to sleep in your king-size master bedroom with 50” flat screen TV and a charming window seat. Your en-suite master bath features a dual vanity, walk-in shower, and a walk-in closet. The second king-size bedroom offers handsome wood furnishings, its own 40” flat screen TV, and two closets. The third bedroom offers two full-size beds. Watch your own 32” TV, and unpack your bags in two generous closets. The fourth bedroom has a king-size bed. Check your emails in the private workspace, watch shows on the 37” wall-mounted flat screen TV, and enjoy direct access to the pool area and patio. The adjoining guest bathroom has a walk-in shower. Just off the main entrance of the home is the third full bathroom with tub/shower combination. Guest amenities include complimentary Wi-Fi, Nintendo Wii, and a washer/dryer. Parking is available for up to four cars in the driveway. All leases require a minimum 31-day term. THE LOCATION Known as the Diving Capital of the World, Key Largo is home to exotic marine life, crystal clear waters, and beautiful white-sand beaches, Key Largo offers no shortage of ways to spend time outdoors. Bring along your boat to experience firsthand North America's only coral reef. Explore Everglades National Park to spot manatees, alligators, and birds. Hop in the kayaks we’ve set aside for you, and paddle along the canal. Or take to the waters by standup paddleboard and keep an eye out for fish swimming near the surface. Taste local seafood at Lazy Lobster, a 6-minute walk from your door. And afterward, indulge your sweet tooth with a fresh cone from Mr. C's Homemade Ice Cream (7 minutes on foot). Drive straight to your rental and access the home with your unique lock code. When you book, we will send you our mobile app with directions and home instructions. We’re available 24 hours a day with live help. Each reservation includes applicable taxes, cleaning fee, and Property Damage Protection policy.
  • Take in Ocean Views

    Take in Ocean Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #241694
    $188 to $491 USD/night  
    Take in ocean views from the expansive rooftop deck of this 3BR/3BA Marathon home, featuring a master suite with new king bed and private deck. Make use of the complimentary bicycles and complex pool, and enjoy free membership to the Cabana Club. Sleeps 8.. Take in ocean views from the expansive rooftop deck of this 3BR/3BA Marathon home for eight. Your spacious master suite includes a new king bed and private deck. Spend time enjoying the sublime Florida weather on your covered patio and two-story deck. Pedal around the neighborhood on the bicycles provided and cool off with a refreshing dip in the complex pool. The home is located directly across the street from the boat house, where you can store and launch your boat for a fee. Plus, enjoy free membership to The Cabana Club beach and pool. ABOUT THE HOME Cool tile flooring flows throughout the open-concept living area, featuring exposed wood beams and floods of natural light. Settle onto the comfy sectional sofa with seating for five, and catch your favorite shows on the 46” wall-mounted flat screen TV. Whip up brunch in the granite kitchen with stainless steel appliances. Sip morning coffee at the breakfast bar for two, or gather for full meals at the glass dining table set for six. After a fun-filled day at the beach, fire up the grill on your covered patio, and dine alfresco at the table for four. The shaded porch swing offers a lovely spot to sit and read. Move to the upper deck with open-air dining for seven, or ascend the spiral staircase to your private 700-square-foot rooftop deck with outdoor shower. Soak up the Florida sunshine from two chaise loungers, or relax in the shade with a refreshing drink in hand. Whichever seat you choose, breathtaking ocean views are on full display. In the evenings, rest up in three spacious bedrooms with their own private bathrooms. The king-size master suite boasts a large walk-in closet, a 32” flat screen TV, and a private balcony with hammock chairs and a bistro table for two. Your en-suite master bath is configured with a walk-in shower and luxurious jetted tub. In the second bedroom, drift to sleep in the queen-size bed, watch your own 32” flat screen TV, and wake each morning to refresh in the en-suite bath with tub/shower combination. Upstairs, the third bedroom offers two twin beds, ample closet space, and a 37” flat screen TV. Next door, the third bathroom is equipped with a walk-in shower. Extras at this vacation home include complimentary Wi-Fi, Netflix, a washer/dryer, beach essentials, two bicycles, and parking for two cars under the house. THE LOCATION During your stay at this Marathon vacation rental, pedal around the neighborhood on the bicycles set aside for you, and cool off with a refreshing dip in the oceanfront complex pool. For a small fee, store and launch your boat at the Boat House across the street, and spend leisurely afternoons cruising on the water. Drive 4 minutes to The Cabana Club in Key Colony Beach, where you’ll have free member access to the private beach and pool club. Recline poolside at The Cabana Club Island Bar & Lounge, a local favorite for tropical cocktail specials. Treat yourself to dinner at the Island Fish Company, and enjoy seafood classics at a waterside table (only an 8-minute walk from your door).
  • Perched on the Largest

    Perched on the Largest

    Marathon: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 10
    • #240137
    $320 to $632 USD/night  
    Perched on the largest deep water canal in the Florida Keys, this fresh 4BR/3BA home offers a large boat dock, a glittering pool, and both a fish cleaning station and a dedicated freezer. Newly updated with ceramic tile floors and mermaid décor. Sleeps 8.. Relish in emerald canal views at this lovely 4BR/3BA Key Colony Beach home, complete with a spacious waterside deck and sparkling private pool. New wood-grain ceramic tiles line every room, with fun mermaid accents greeting you at every turn. Bring your boat along or rent one nearby to make use of your large, private dock. Anglers will appreciate the fish cleaning station and dedicated freezer. ABOUT THE HOUSE New ceramic tile lines the floors of your freshly updated home, with playful mermaid décor lighting up each room. The open-concept living room boasts a massive sectional couch and a recliner for movie nights and TV marathons on the 55” flat screen TV. White appliances and cabinetry gleam in the kitchen, where expansive granite counters make meal prep a breeze. Find all the gadgetry and cookware you could dream of to fix simple beach picnics or elaborate dinners. Six can sit down to breakfast at the sweeping breakfast bar, with room for eight in the elegant formal dining area. Step out to the patio to find outdoor dining, sun loungers, and a full outdoor living room set. Slip into the pool for a relaxing swim among emerald canal views. Make use of the barbeque grill, along with your large private dock and a dedicated fish cleaning station. There’s also a standalone freezer for storing your catch inside. The king-size master bedroom offers a 42” TV and a pristine en-suite bath with a double-sink vanity and a tiled walk-in shower. The second and third bedrooms both have cozy queen-size beds and a shared en-suite bath with a walk-in shower, and the fourth has two twin-size beds. Another full guest bath is equipped with a tub/shower combination. Extras at the house include driveway parking with room enough for a small RV, a washer/dryer, and complimentary Wi-Fi. THE LOCATION Your Florida Keys home has it all — a private dock on the canal and South Beach's sand, sun, and surf within half-mile from your door. Rent a rig at Miami Five Star in 7 blocks, and dine on everything from pizza to tacos Mediterranean steps away.
  • 14 Night Minimum Stay

    14 Night Minimum Stay

    Key Colony Beach: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #226391
    $171 to $200 USD/night Credit Card
    14 NIGHT MINIMUM STAY. 14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/airconditioning and a private patio or balcony. This unit has a great corner view of the ocean. The kitchen is equipped with stove, refrigerator, dishwasher, utensils, cookware, glass selection and dishes.Linens and towels are also supplied. Cable TV is provided in each unit and on-site Internet wireless access is available at no additional charge. All of the condos are decorated according to the taste of the individual owners 14 night minimum stay per condominium association rules. 14 NIGHT MINIMUM STAY.
  • Located around the Corner

    Located around the Corner

    Key West: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #239593
    $293 to $720 USD/night  
    Located around the corner from Key West’s bustling Petronia Street and Restaurant Row, this 3BR/3BA home boasts a chef’s kitchen with upscale appliances and granite countertops, as well as a private heated pool and tropical deck. Sleeps 6.. Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Step out to your backyard for a dip in the private pool, set amid lush landscaping, and enjoy meals at the outdoor dining table for four. Located three blocks from Duval Street, and just around the corner from lively Petronia Street and Restaurant Row, you’ll find everything from Caribbean eats to crepes to kosher fare, mere steps from your door. You’re also near an array of eclectic independently-run boutiques. ABOUT THE HOUSE Step through the sliding glass doors off the living room to swim in the crystal-clear heated pool with a unique waterfall feature. Linger over al fresco meals among lush tropical gardens. The open-concept living area seats five between a plush sofa and chair; enjoy a 46” flat screen Apple TV and Sonos theater system. The chef’s kitchen makes cooking a pleasure with its granite countertops and stainless-steel appliances that include an oven with warming drawer, and a Thermador four-burner stove with griddle and grill. Enjoy coffee at the kitchen island with seating for three, or dine at the four-person table. When it’s time to turn if for the night, you’ll find a bedroom with two twin beds and a 37” flat screen TV just off of the entryway. A bathroom with a walk-in glass shower sits adjacent. Upstairs, the second bedroom features a queen bed, 37” flat screen TV, walk-in closet, and bathroom with walk-in shower. Down the hall, the master bedroom has a queen-size bed, 42” flat screen TV, walk-in closet, and a luxurious en-suite bathroom with double-sink vanity, large jetted tub, and a separate shower with dual showerheads. Two double doors off the master bedroom lead to a balcony. Guest amenities include complimentary Wi-Fi, Apple TV, a washer/dryer set, and parking for two cars. All leases require a minimum 31-day term. THE LOCATION Situated on a quiet lane in Bahama Village, your rental home is around the corner from many of Key West’s favored restaurants and shops. Traveling with kids. You’re a short drive from the Key West Aquarium and the Mel Fisher Maritime Museum. Have literature lovers in your midst. The Ernest Hemingway Home and Museum is blocks away. And the beach is a 5-minute drive.

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