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 Star Rating
    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, Full Bathroom upstairs, 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.
  • Across the Bay from

    Across the Bay from

    Islamorada: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241141
    $390 to $782 USD/night  
    Across the bay from the Everglades National Park, this 3BR/2BA waterfront home features a private beach, dock, kayak, and paddleboards. You’ll also love being near John Pennekamp Underwater State Park for premier diving. Sleeps 8.. Situated on the beautiful Florida Bay, this 3BR/2BA Islamorada home offers an idyllic waterfront haven with its own private beach, dock, kayak, paddleboards, and sprawling backyard with a volleyball net. Spend leisurely afternoons fishing off the dock before cooking up your catch on the grill. Enjoy your meal at the six-person patio table, then relax in one of two sun loungers. Or enjoy spectacular sunsets from the waterside hammock. Conveniently located, this home sits across the bay from the entrance to Everglades National Park. Nestled between Snake and Tavernier Creek, you’ll also be close to premier snorkeling and diving at Pennekamp Underwater State Park -- just 15 miles away. ABOUT THE HOUSE This home features a welcoming open floor plan with cool, tiled flooring and an abundance of natural light. After a day of fishing or diving, kick back in the main living area with a couch, love seat, and oversized chair. Enjoy your favorite shows on the 65” flat screen HDTV. Find more space to unwind in the adjacent sunroom, furnished with a couch, love seat, and two inviting armchairs. Play a board game or a round of cards at the four-person glass top table. It’s easy to whip up meals in the spacious kitchen, equipped with high-end appliances. A three-person kitchen bar offers a casual spot to chat while the chef preps dinner. In the dining area, there’s room for six to enjoy meals amid spectacular sunset views across the bay. With sleeping space for up to eight, this house features three bedrooms, each equipped with an AIR CONDITIONING unit to ensure a good night’s sleep. The master bedroom includes a stately king-size bed and a large closet. Across the hall, another king bed awaits in the second bedroom, which also has a large closet and a convenient office nook. Guests in these rooms share a bathroom with a walk-in shower. In the third bedroom, you’ll find two twin-over-full bunk beds and a Jack-and-Jill bathroom (shared with the sunroom) with a walk-in shower. Outside, the tropical backyard provides a direct view of the Florida Bay as well as its own private beach. This outdoor retreat has it all: a full-size sand volleyball court, outdoor dining, a charcoal grill, a fire pit, and a private dock with outdoor seating. Additional guest amenities include complimentary Wi-Fi, cable TV, a washer/dryer, and parking for four cars in the driveway. All leases require a minimum 31-day term. THE LOCATION Within a 30-minute drive, John Pennekamp Coral Reef State Park offers some of the best diving in the U.S. Along with superb snorkeling, sailing, and glass-bottom boat tours. Spend the day exploring the park’s 70 nautical square miles of Atlantic Ocean waters, or head across the bay to enter the Everglades National Park for wildlife sightings and thrilling swamp tours. For more outdoor adventures, swim with dolphins at Theater of the Sea (an 8-minute drive), and hit the hiking trails in Windley Key Fossil Reef Geological State Park (6 minutes). When dining out, head to Marker 88 for a laid-back beachfront grill specializing in seafood and cocktails. Or go for craft beers and hamburgers at MEAT Eatery & Tap Room. Both are within a 7-minute walk.
  • Kick off your Sandals

    Kick off your Sandals

    Islamorada: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #238432
    $193 to $345 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
    $459 to $1,176 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.
  • 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.
  • Newly remodeled home in

    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242078
    $549 to $799 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.
  • Take in Sweeping Azure

    Take in Sweeping Azure

    Tavernier: Vacation Rental
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #243990
    $139 to $399 USD/night  
    Take in sweeping azure blue water views of the Florida Keys from a third-floor balcony at this 1BR condo. Luxurious Ocean Point amenities include a shared pool and spa, private beach access, grill area, and a protected marina with a boat dock. Sleeps 4. Situated in the 69-acre Ocean Pointe community, this third-floor 1BR condo features a balcony with views over a protected mangrove forest to the beach and sparkling ocean beyond. Luxuriate in the shared pool and spa, stop by the new pool bar, dig your toes into the sand on the private beach, explore the boardwalk to a gazebo at the ocean’s edge, or play tennis on the lighted courts. Enjoy access to a protected marina with a boat ramp, boat storage, and dock. LIVING AREA Tile floors and ceiling fans keep this home cool while colorful marine-themed artwork brightens the space. Settle into the queen-size sleeper sofa and watch favorite shows on a 42” flat screen TV or simply look out the sliding glass doors and take in the stunning view. KITCHEN & DINING Whatever menu you dream up, the well-stocked and updated kitchen has all the culinary tools needed. Featuring stainless steel appliances including an electric stove/oven, fridge with ice maker, dishwasher, and microwave as well as a breakfast bar with seating for two. The dining area offers a glass-topped table that seats four. BEDROOM & BATH After a fun-filled beach day, lay back and enjoy the sheer comfort of the queen-size bed. Watch shows on the 39” flat screen TV. A wood dresser and ceiling fan complete the bedroom. The en-suite bathroom features a Jacuzzi tub/shower combination. OUTDOOR AREA Breathe the fresh air on the balcony with 180-degree views of the protected mangrove forest, the beach, and sparkling waters beyond. EXTRA AMENITIES Ocean Point amenities include access to a protected marina, direct beach access, a new ocean boardwalk and gazebo, grill area, heated pool, Tiki Hut pool bar, kayak rentals, and spa as well as tennis and basketball courts. Unassigned parking is available for two vehicles in the outdoor parking lot. A washer/dryer and complimentary Wi-Fi are provided. THE LOCATION Tavernier is located on Key Largo, a 27-mile spit of land extending into the Gulf of Mexico. A mecca for snorkelers and scuba divers, Key Largo is approximately 2 hours north of Key West. The John Pennekamp Coral Reef State Park features a number of reefs and sunken ships that play host to a wide array of colorful marine life. The 510-foot Spiegel Grove landing ship was sunk in 2002 to create an artificial reef. Make a reservation to tour Island Dolphin Care providing dolphin therapy for special needs children and adults. Drive 5 minutes and visit local favorite Harriette’s Restaurant dishing up mouthwatering biscuits and conch burgers. Check out the Blond Giraffe Key Lime Pie Factory for its namesake dessert. Upon arrival, easily access your condo 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, and linens. Your home will include a HomeDroid tablet (electronic guest directory) providing specific home details, local suggestions, Wi-Fi access, and TV instructions. If you need anything at all before, during, or after your stay, our 24/7 local team is always ready to help!
  • Escape to this 2br

    Escape to this 2br

    Marathon: Vacation Rental
    • 2 BDR
    • 1 BA
    • Sleeps 6
    • #241101
    $206 to $564 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!
  • Take in Ocean Views

    Take in Ocean Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #241694
    $159 to $443 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).
  • We Guarantee all Listing

    We Guarantee all Listing

    Marathon: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 10
    • #243237
    $217 to $524 USD/night  
    We guarantee all listing information is accurate and up to date. From the moment you book, you’ll be provided timely and helpful communications regarding your trip. Upon arrival, easily access your home 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!
  • Newly remodeled home in

    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242079
    $549 to $799 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.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241323
    $226 to $695 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.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #241322
    $222 to $662 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.
  • Situated in an Exclusive

    Situated in an Exclusive

    Key West: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242177
    $243 to $543 USD/night  
    Situated in an exclusive gated enclave, this brand-new 3BR/3.5BA offers a private elevator, patio, five balconies, and community pool access. Located in the heart of Key West, the Old Town district boasts great shopping, dining, and entertainment. Sleeps 6. PROPERTY OVERVIEW Situated in the exclusive gated enclave of Old Town Villas at Key West, this stunning brand-new 3BR/3.5BA townhome offers a private elevator, patio, five balconies, and community pool access. Relax in one of two living rooms with large HD TVs, or simply watch the sun set from the private terrace in your bedroom. Located in the heart of Key West, the Old Town district boasts epic shopping, dining, and entertainment. LIVING AREAS This luxurious townhome is designed to blend classic Key West style with modern upscale comforts. The inviting open-concept downstairs living room has ample seating, a 55” HD TV, and balcony access, while the upstairs family room offers a 55” HD TV, a wet bar with a wine fridge, and a large balcony with a table seating for five. An upstairs study is a great place to read or check emails. Step out onto the rooftop balcony to enjoy the marina views. KITCHEN & DINING The chef in your group will appreciate the gourmet kitchen with high-end stainless steel appliances, expansive granite counters, a double sink, glass-top range, and bar seating for four. When it’s time to eat, gather around the dining table with seating for six. BEDROOMS & BATHS Find quiet privacy in the master bedroom with a stately king bed, a spacious walk-in closet, a private balcony, and a 48” HD TV. Refresh in the en-suite bathroom with a double vanity, a jetted soaking tub, and a walk-in shower with a rainfall showerhead. The junior master bedroom boasts a king bed, walk-in closet, private balcony, 32” HD TV, and an en-suite bathroom with a walk-in shower. The third bedroom provides two twin beds, a 42” HD TV, two closets, and an en-suite bathroom with a walk-in shower. A half bathroom is located on the top floor off the second living room. OUTDOOR AREAS Kick back on the ground floor patio, enjoy some personal time on one of two private balconies, or watch the sun set from the rooftop terrace. Spend sun-drenched afternoons at shared year-round (unheated) pool, then gather your party for an al fresco meal on the top story balcony with a table and chairs for five. EXTRA AMENITIES & DETAILS Perks include complimentary Wi-Fi, a private in-home elevator, and a washer/dryer. On-site parking is limited to one car in the garage; additional paid parking is available nearby. All leases require a minimum 31-day term. THE LOCATION When dining out, visit local favorite Michael’s Restaurant for American dishes and fondue offered in a sophisticated atmosphere with a garden patio and outdoor bar. Or check out Caroline’s Cafe for po' boys and conch fritters in a circa-1838 house with outdoor seating. Take a five-minute walk to the Key West Aquarium which features a touch tank for hands-on experiences, plus free guided tours. Upon arrival, easily access your vacation home 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!
  • Soak in Water Views

    Soak in Water Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #238859
    $157 to $446 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.
  • 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.
  • This 2br/2ba with Canal

    This 2br/2ba with Canal

    Key Largo: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 8
    • #238387
    $185 to $247 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.
  • This 4br/3ba Key Largo

    This 4br/3ba Key Largo

    Key Largo: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 6
    • #242718
    $353 to $728 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.
  • 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.
  • 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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