Key West Vacation Rentals

If you have never been to Key West, you are in for a real treat. There are attractions for everyone and villa rentals, condo rentals, and vacation rentals to suit every need.

Key West is an island in the Straits of Florida at the southernmost tip of the Florida Keys. With a variety of accommodations, the island is about 4 miles long and 2 miles wide. Home to balmy weather and crystal blue skies, the island is famous for its diving, fishing, water sports and golfing. Many visitors rent a bicycle and explore the history and architecture of Old Town Key West. Walking tours and the Sunset Celebration at Mallory Square is a daily spectacle for visitors and residents. Boat excursions and tours provide a great way to view Key West from the water. Or come just to stroll along the harbor walk or dine at one of the many restaurants.

Owner Direct Vacation Rentals lets you discover the magic of Key West. However you choose to see the town, you'll discover that old town Key West is one of America's true architectural and botanical treasures. The streets, filled with sidewalk cafes, open-air bars, legendary pubs and world-class restaurants come alive. Discover a city where real estate titles date back to the Kings of Spain. One of Key West's best attractions is that no matter what time of the year you come here, there is always something going on. Choose your accommodation: a condo rental, villa rental or one of many other types of Florida accommodations to make your holiday extraordinary.

Although vacation rentals near Disney World are popular, Key West is a very fun place and can be as relaxing, romantic, or wild as you want it to be. There is lodging in Key West for every type of traveler. We have some of the most extravagant villa rentals and villas with beautiful tropical landscaping and free form pools. Diving and snorkeling the coral reefs and wrecks around Key West are spectacular. Tropical fish are abundant on the reefs and there is snorkeling available on a sailing catamaran or schooner out to the reef for a day of fun.

Owner Direct Vacation Rentals is a unique vacation home rental “matching service” that makes finding a perfect accommodation or villa rental quick and easy.

Thinking about your fresh seafood dinner at one of the fine Key West restaurants? One thing you can bank on while in Key West - fresh local seafood. Outside dining seems to be the favorite because those restaurants come with a view. Some have a beautiful view of the sunset, others have a view of Duval Street and downtown Key West, which can get interesting the further into the evening you stay.

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  • On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    2 BDR • 2 BA • Sleeps 5 • #69125
    245 to 405 USD/night
    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.
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  • Executive Bay 2 / 1.5

    Islamorada: Executive Bay Club: Townhouse in a gated community
    2 BDR • 2 BA • Sleeps 4 • #234599
    136 to 141 USD/night
    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.
  • Islamorada Luxury Condo

    Islamorada: Bay Harbour: Condo in a gated community
    2 BDR • 3 BA • Sleeps 6 • #209708
    243 to 343 USD/night
    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.
  • New Listing! Waterside

    Key Largo: Vacation Rental
    4 BDR • 2 BA • Sleeps 8 • #253128
    162 to 401 USD/night
    Located in Key Largo's prestigious Buccaneer Point, this custom 4BR home occupies a 12,000 square foot waterfront lot! Enjoy direct access to the bay, complimentary kayaks, a gourmet kitchen, and a gazebo sitting area in the large backyard. Sleeps 8.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** Located in Key Largo's prestigious Buccaneer Point, this custom 4BR/2BA home offers an idyllic waterfront setting on a 12,000 square foot lot! Enjoy direct access to the bay via a channel through the mangroves. Complimentary kayaks and a paddleboat are available for guest use. This home also boasts a screened private balcony, a large backyard with a convenient grill, and a gourmet kitchen with gleaming granite counters and stainless steel appliances. LIVING AREA Relax in a welcoming living area, appointed with two comfy couches, a reclining chaise lounge chair, and a 65'' flat-screen TV that’s ideal for movie nights. KITCHEN & DINING The gourmet kitchen boasts expansive granite counters and ample cookware. A full suite of stainless steel appliances includes a professional-grade gas range and roomy French door refrigerator. A three-person breakfast bar offers a casual spot to chat while the chef preps dinner. Nearby, a light-filled dining area seats four. BEDROOMS & BATHS This two-story home sleeps up to eight guests between four bedrooms. The spacious master bedroom offers a king bed and 46'' flat-screen TV. An en-suite bathroom features a jetted tub and a beautiful walk-in shower. A second bedroom has a queen bed and 32” wall-mounted TV, while a third bedroom features a queen bed and large desk area. The fourth bedroom is appointed with an inviting king bed. A guest bathroom is configured with a walk-in shower. OUTDOOR AREAS Step out for fresh air anytime on your screened private balcony, detailed with seating for two. The backyard offers a lush and private oasis of swaying palms. Barbecue burgers on the convenient grill and follow the paved footpath straight to the waterfront! EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi, cable TV, a washer/dryer. Guests also have access to five kayaks and a paddleboat. This home has driveway parking for four. The main entrance of the home is accessed via a flight of exterior stairs. THE LOCATION Drive 5 miles to John Pennekamp Coral Reef State Park -- offering the best diving in Florida. Or drive across the bay to stunning Everglades National Park (38.5 miles) for a day of wildlife spotting and outdoor adventures. Enjoy hiking and learning about local geology and botany at Windley Key Fossil Reef Geological State Park (14 miles), and meet rescued birdlife at Florida Keys Wild Bird Rehabilitation Center (5.1 miles). This home is also within 1-2 miles of great local eateries and shops.
  • New Listing! Oceanfront

    Islamorada: Vacation Rental
    3 BDR • 3 BA • Sleeps 6 • #253798
    225 to 253 USD/night
    This double-waterside home is a tropical dream! Your 3BR retreat boasts coastal-chic interiors and lovely ocean views, as well as canal frontage and private beach access. Highlights include a boat dock, a fish cleaning station, and kayaks. Sleeps 6.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** Perched across the lane from a white sand private beach and abutting the canal, this double-waterside home is a tropical paradise. Your renovated 3BR/3BA retreat features coastal-chic interiors and large picture windows that face the ocean. With lovely views and direct canal access, your home has all the bells and whistles for a dream vacation. Highlights include a private boat dock, a fish cleaning station, and two kayaks. With the private beach just steps away, this rental is ideal for island adventures. LIVING AREA Unwind in the sun-kissed living room, furnished with matching recliners, a love seat, and a sofa. Gather around the 40” flat-screen TV for a relaxing movie night. KITCHEN & DINING Whip up gourmet creations in the fully stocked kitchen, outfitted with stainless steel appliances and ample counter space. When it is time to eat, share meals at the dining table for six. BEDROOMS & BATHS This two-story home sleeps up to six guests between three bedrooms. Sleep soundly in the inviting master bedroom, appointed with a king bed and a 32” flat-screen TV. The en-suite master bathroom includes a walk-in shower. The second bedroom features a queen bed, a 40” flat-screen TV, and direct balcony access. A full bathroom is configured with a walk-in shower. The third bedroom studio is outfitted with two twin beds and a 40” flat-screen TV. A kitchenette is equipped with a wet bar, a toaster oven, and a microwave. The en-suite bathroom has a tub/shower combination. OUTDOOR AREAS Your rental is 150’ from the sparkling ocean – just across the adjacent open lot! Located on a quiet dead-end street, your tropical oasis includes a private boat dock with a convenient fish cleaning station. Spend leisurely afternoons lounging underneath your canal-side palapa. When evening falls, sizzle your fresh catch on the gas grill. Enjoy the breeze and incredible beach views from the private porch and balcony, both furnished with ample seating. EXTRA AMENITIES & MORE DETAILS Parking is available for four vehicles between the carport and the driveway. There is a side area for trailer parking only (if you choose to bring a boat). Complimentary Wi-Fi, cable TV, and a washer/dryer are provided. Extras include two fishing kayaks. The on-site 70’ long boat dock that can accommodate a large boat, or two 25' boats. There is a boat ramp next door to the home (free of charge). The cargo lift and boat lift are not available for guest use. The second-floor main living area of the home is accessed via a flight of exterior stairs. The separate downstairs studio has its own entrance. THE LOCATION Islamorada holds the title as the Sport-Fishing Capital of the World. Adventurers will love embarking on eco-tours, fishing expeditions, and snorkeling, all within minutes from your rental. Don’t miss a trip to the History of Diving Museum, home to an excavated 16th-century treasure chest. Visit the charming Morada Way Arts & Cultural District -- where you’ll find delicious restaurants, galleries, and boutique shops.
  • Marlin Bay Resort & Marina

    Marathon: Vacation Rental
    3 BDR • 3.5 BA • Sleeps 8 • #242079
    599 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.
  • New Listing! Spacious

    Tavernier: Vacation Rental
    6 BDR • 5 BA • Sleeps 14 • #252416
    280 to 424 USD/night
    With 4,900 square feet of luxurious living space, this 6BR waterfront retreat is comprised of a spacious home and separate studio. Your tropical getaway features a palatial master suite, a game room, two kitchens, and a 70’ deepwater dock. Sleeps 14.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** Sail right up to your gated three-story getaway, highlighted by a private 70’ dock with direct ocean access. With 4,900 square feet of luxurious living space, this 6BR waterfront retreat is comprised of a spacious 5BR home and separate 1BR studio. Highlights include a well-equipped game room, two kitchens, and a palatial master suite. After a leisurely day on the water, enjoy breathtaking sunsets on the private waterfront balconies and deck. LIVING AREAS Make yourself at home in the second-floor living room, detailed with beach-chic decor, a comfy oversize sectional, and a 65” HDTV. Play a friendly game of pool, tennis, or foosball in the third-floor game room. Or settle in and watch a movie on the sleeper sofa. The studio occupies the entire first floor and has a cozy living area of its own, featuring plush seating and a 43” HDTV. KITCHEN & DINING The chef in your group will appreciate the gourmet second-floor kitchen, outfitted with ample granite counter space to prepare home-cooked meals. Chill favorite bottles in the convenient wine fridge. While dinner simmers, perch at the kitchen bar with seating for four. Or gather at the dining table with seating for seven. The studio also has a fully stocked kitchen, as well as a breakfast table for four. BEDROOMS & BATHS This three-story retreat sleeps up to 14 guests between the six bedrooms and a sleeper sofa in the game room. Sleep like royalty in the third-floor master suite, appointed with a king bed, huge walk-in closet, and covered waterfront balcony. Watch favorite shows in the sitting area on a flat-screen TV. The open-concept en-suite bathroom boasts a double vanity, walk-in shower, and jetted soaking tub. The second floor is configured with four more sunlit bedrooms. The second bedroom is furnished with a king bed, while the third and fourth bedrooms each hold a queen bed. The fifth guest room has a twin-over-queen bunk bed, and two adjacent bathrooms each have a tub/shower combination. The studio includes a queen bed, flat-screen TV, and bathroom with a walk-in shower. Find an additional bathroom with a walk-in shower off the game room. OUTDOOR AREAS Sip morning coffee on the huge back porch or covered second-floor balcony. Then embark on a coastal adventure straight from your backyard! Walk right down to your 70’ private deepwater dock and take advantage of direct ocean access. Make use of two provided kayaks and explore the gorgeous Upper Keys. EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi and a washer/dryer. Parking is provided for up to four vehicles (two under the carport and two in the driveway). Please note that street parking is not available. THE LOCATION Snorkel at John Pennekamp State Park, home to the only living coral reef in the country. Experienced boaters can explore Everglades National Park, just across the Florida Bay.
  • Waterfront 2BR w/ Huge

    Marathon: Vacation Rental
    2 BDR • 2 BA • Sleeps 8 • #243237
    263 to 423 USD/night
    Enjoy access to the gulf and ocean, dock your boat along the seawall, and watch dreamy sunsets from a large sunroom. Walk minutes to dining. Sleeps 10.. Enjoy expansive views of Boot Key Harbor at this waterfront 2BR/2BA (plus loft) duplex in Marathon, with easy access to the ocean and gulf. After a day on the water, dock your boat along the 45-foot seawall. Then gather to watch gorgeous sunsets from a large sunroom overlooking the water. The home offers a great walkable location, with restaurants and entertainment just a few minutes away from your door. Head across the street to Florida Keys Country Club (open to the public) and enjoy the beautiful 18-hole golf course and tennis courts. Or grab bikes and cycle around the course’s winding trail. Beautifully furnished throughout, this contemporary duplex accommodates up to ten guests between two bedrooms and a spacious lofted sleeping area. ABOUT THE HOUSE The sunny and inviting living room beckons you home after a day at the coast. A leather couch and two armchairs sit beneath tall vaulted ceilings, and there’s a 50" flat screen HDTV for group movie nights. A beautiful sunroom boasts gorgeous views across Boot Key Harbor. Enjoy morning coffee in the love seat while gazing across the water. Later, gather for lazy lunches at the dining table with seating for four. A contemporary kitchen gleams with black granite countertops and stainless steel appliances. There’s plenty of room to stash groceries and snacks in a roomy side-by-side refrigerator. A two-person dining table in the kitchen offers a casual spot for breakfast. This rental sleeps up to ten guests in the two bedrooms and loft bedroom (doesn’t have a door). Ocean greens and blues create a serene ambience in the master bedroom — featuring a king bed, double door closet, and a 32” wall-mounted HDTV. Freshen up in an en-suite bathroom with a dual vanity and tub/shower combination. Guests in the second bedroom can rest in comfort in a queen bed. Find sleeping space for six in the expansive loft area, featuring two full-size beds, a queen sleeper sofa, and a sitting area with a glass-top table and chairs. In addition, the house has a guest bathroom with a stylish tile walk-in shower, complimentary Wi-Fi, cable TV, and a washer/dryer. The driveway offers parking space for two vehicles. THE LOCATION With a beautiful waterfront setting on Boot Key Harbor, you might be tempted to kick back at home for the duration of your stay. But tear yourself away, and you’ll find Marathon has countless attractions to fill your days. Drive 8 minutes to the palm tree-dotted shores of Sombrero Beach — one of the most stunning beaches in the Florida Keys. Golf lovers can stroll across the street from home for a round on the 18-hole public course at Florida Keys Country Club. Bringing the kids. Drive 7 minutes to Florida Keys Aquarium Encounters. Or head the same distance to hike amid the mangroves and forest of Florida Keys Wildlife and Environmental Area. Restaurants, bars and shops are within a 15-20 minute walk, while the majority of dining options are a 5-minute drive away. Sample tasty Keys specialties (Including alligator tail) at The Stuffed Pig, or indulge in fabulous local seafood fresh off the boat at Barracuda Grill. Upon arrival, easily access your unit 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, 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!
  • Bayside 3BR/3BA w/ Heated

    Marathon: Vacation Rental
    3 BDR • 3 BA • Sleeps 8 • #238859
    225 to 416 USD/night
    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.
  • Canal-Side 4BR Home w/

    Marathon: Vacation Rental
    4 BDR • 3 BA • Sleeps 10 • #240137
    344 to 753 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.
  • Luxury Home w/ 180-Degree

    Cudjoe Key: Vacation Rental
    3 BDR • 2.5 BA • Sleeps 6 • #253797
    226 to 248 USD/night
    You’ll be wowed by the epic 180-degree bay views at this 3BR Cudjoe Key home. Completely remodeled, this luxury home includes a chic chef’s kitchen, huge wraparound deck, two private boat docks, a firepit, and multiple outdoor seating areas. Sleeps 6.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** You’ll be wowed by the incredible 180-degree bay views at this 3BR/2.5BA home, located in Cudjoe Key. Completely remodeled inside and out, this high-end home boasts a stunning chef’s kitchen, huge wraparound deck, and multiple outdoor seating areas. Two private docks are ideal for fishing or mooring a small boat, and an outdoor firepit offers a tranquil spot beside the water for end-of-day drinks. LIVING AREA Vaulted ceilings soar above the welcoming living area. Recline on a pair of comfy sofas and take in the dramatic bay views. Watch a movie on the 36” flat-screen TV, or rack up the nearby pool table! KITCHEN & DINING Flex your culinary muscles in the spectacular kitchen. This ultra-modern cooking space boasts glossy white cabinetry and a full suite of stainless steel appliances -- including a roomy side-by-side refrigerator. A big kitchen island seats four -- a fabulous spot for casual dining. Nearby, a dark wooden dining accommodates six for festive vacation meals. BEDROOMS & BATHS This two-story home sleeps up to six guests between three stylish bedrooms. Full of coastal light, the master bedroom offers bay views, a queen bed, and access to the deck. A chic en-suite bathroom has a double vanity, walk-in shower, and inviting jetted tub. Upstairs, the second and third bedroom each have bay views, a queen bed, and a window-side sitting bench. The third bedroom also offers deck access. Adjacent, a sparkling guest bathroom is appointed with a double vanity and walk-in shower. A half bath provides added convenience. OUTDOOR AREAS A wraparound deck wows with gorgeous 180-degree views of Cudjoe Bay. Sip morning coffee at the bistro tables, or savor alfresco meals around the eight-person dining table. Beneath the house, there’s a picnic table, ping-pong table, gas grill, and a large lounge area with ample seating right by the bay! You’ll also find a firepit area, and two private docks for fishing or mooring a small boat (up to 16’ in length). EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi, a washer/dryer, and two kayaks. There’s parking for up to six vehicles (four under the home and two in the driveway). Boat trailer parking is available. The main entry-level of the home is accessed by a set of stairs. Use of the boat dock is available with a $15 daily fee. A boat launch is within a 7-minute drive at Cudjoe Gardens Marina. THE LOCATION Spend the day kayaking or boating the waters of Cudjoe Bay. Or walk minutes to arrange trips with a local fishing charter. The sandy shores of Bahia Honda State Park are only 14.8 miles away, and wildlife lovers will enjoy nature spotting around Florida Keys (6. 8 miles) and National Key Deer Refuge (8.6 miles).
  • Modern Coco Plum Estate w/

    Marathon: Vacation Rental
    4 BDR • 4 BA • Sleeps 10 • #253340
    502 to 1,023 USD/night
    Boasting 3,356 square feet of state-of-the-art comfort, this new 4BR home is a fabulous Coco Plum getaway. Walk to the beach or cast off from the backyard dock. Lavish outdoor areas include an alfresco kitchen and sparkling pool with a hot tub. Sleeps 10.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** Newly built in Coco Plum, this 4BR/4.5BA estate features an opulent interior and luxe alfresco social spaces. Sunbathe on a sugar-white sand beach across the street, dip in the private pool, and unwind in the hot tub. A backyard dock provides easy access to deep-sea adventures. Bonus: two kayaks are provided for guest use! This home boasts three light-filled levels of modern comfort and stylish design. Other highlights include a high-end kitchen and serene marina views from the balconies. LIVING AREAS Ample plush seating awaits in the sunny living area. Watch movies on the 65” flat-screen TV. An impressive whole-house sound system allows you to cast audio to every room. Two love seats by the third-floor balcony offer a comfy reading nook on quiet afternoons. KITCHEN & DINING Indulge your inner chef in the kitchen, appointed with granite countertops and handsome custom cabinetry. A large island provides seating for four. Stainless steel amenities include a wine fridge and GE Monogram appliances. At mealtimes, gather around the table for six in the dining area. BEDROOMS & BATHS This home sleeps up to 10 guests between four bedrooms, a sleeper sofa in the living area, and two twin-size sleeper sofas on the third floor. Discover comfort and privacy in the spacious master bedroom, outfitted with a king bed and a 65” TV. The en-suite bathroom is configured with a double vanity and walk-in shower. Luxuriate in the bathtub while watching favorite shows on the 52” wall-mounted TV. The second bedroom features two comfy twin beds and a 42” TV. The second bathroom includes a walk-in shower. Sleep soundly on a plush queen bed in the third bedroom. The 42” TV is perfect for movie nights. An en-suite bathroom has a tub/shower combination. The fourth bedroom offers a queen bed, a 42” TV, and an en-suite bathroom with a walk-in shower. A half bath near the pool provides added convenience. OUTDOOR AREAS The back patio boasts a fully loaded outdoor kitchen with a gas grill, stovetop, mini-fridge, and wall-mounted TV. Enjoy meals around the dining table for four on the first balcony, which also features a shaded seating area. Peaceful marina views await on the second balcony. Soak up the sun in a chaise lounge by the sparkling unheated pool. At night, unwind in the hot tub and watch the stars come out. A storage room by the pool holds beach toys and an extra refrigerator. The dock behind your home includes a private slip and a fish-cleaning station. EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi, a washer/dryer, and two kayaks, as well as parking for four cars and a boat trailer in the driveway. THE LOCATION Enjoy easy access to the beach, the Florida Keys Aquarium Encounters, and ocean-view eateries in central Marathon.
  • Marlin Bay Resort & Marina

    Marathon: Vacation Rental
    3 BDR • 3.5 BA • Sleeps 8 • #242078
    599 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.
  • Canal-Front 4BR w/ Private

    Marathon: Vacation Rental
    4 BDR • 3 BA • Sleeps 8 • #245109
    269 to 601 USD/night
    Enjoy a fabulous adventure in the Florida Keys at this luxurious, newly constructed 4BR/3BA canal-front getaway with a private pool. Bring your boat and tie up at the private dock, or explore the canals on a fleet of provided kayaks. Sleeps 8.. This gorgeous, newly constructed 4BR/3BA canal-front duplex property in Sombrero Beach offers the perfect Florida Keys getaway. With a private pool and a dock that can accommodate up to a 30’ boat, as well as a provided paddleboard and four kayaks, this rental offers unparalleled access to water adventures. Follow the canal all the way out to the open waters of the Atlantic Ocean where world-class fishing and diving awaits. Take advantage of the prime location and spend a day at the beach, or walk to local restaurants and attractions in Sombrero Beach. LIVING AREAS After a fun-filled day in the sun, relax in the living room, which is outfitted with a leather sofa and a plush armchair. Watch a movie on the 50” TV, and enjoy direct access to the balcony. KITCHEN & DINING Whip up delicious vacation meals in the gourmet kitchen, fully stocked with everything you might need. The chef in your group will appreciate the gleaming granite countertops and a full suite of stainless steel appliances. Perch at the kitchen bar with seating for three, or savor a family meal at the four-person dining room table. BEDROOMS & BATHS This home includes four bedrooms that sleep up to eight guests. Three full bathrooms are each stocked with a complimentary starter supply of toiletries and bath amenities, as well as plenty of plush towels. Retreat to the tranquil master bedroom, which has a king bed and a 32” TV, as well as two closets and a chest of drawers. The en-suite bathroom has a tub/shower combination and can also be accessed via the hallway. The second bedroom offers a queen bed and a 32” TV, while the third guest room features a twin-over-queen bunk bed and a 32” TV. A second bathroom is equipped with a tub/shower combination. Stretch out on a king bed in the fourth bedroom, which also offers a 32” TV. Curl up with a good book on the chaise lounge and enjoy the stunning canal views. An en-suite bathroom provides a double vanity and a walk-in shower. OUTDOOR AREAS Step out to your private backyard oasis. Take a refreshing dip in the heated outdoor pool, or gather around the table with seating for five on the covered patio. Watch the big game on the 32” TV while you barbecue burgers on the gas grill. The covered patio also provides a mini fridge and a bait freezer. This canal-front home has a private dock, and you can bring your own boat or utilize the provided kayaks and paddle board. A covered balcony off the living room invites you to kick back and enjoy the canal view while sipping a crisp beverage. EXTRA AMENITIES & DETAILS Guest amenities at this dog-friendly home include complimentary Wi-Fi and a washer/dryer. Covered parking is available for two vehicles under the carport, with parking for two additional cars and a boat trailer in the driveway. Please note, this rental has a 7-night minimum stay requirement. THE LOCATION Your rental is located in the welcoming community of Sombrero Beach. Walk to the grocery store, dining, and the Sombrero Beach Golf Course, or drive just 6 minutes to the sparkling sands of Sombrero Beach. 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!
  • Waterfront 3BR w/ Private

    Islamorada: Vacation Rental
    3 BDR • 2 BA • Sleeps 8 • #241141
    391 to 391 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.
  • Canal-Front Dream w/

    Marathon: Vacation Rental
    4 BDR • 3 BA • Sleeps 8 • #253342
    363 to 873 USD/night
    This 4BR canal-front home is just minutes from the beach! Spend hours of fun in the backyard oasis, complete with a private heated pool, spa, and boat dock. A lovely screened porch is the perfect place to end the day with after-dinner drinks. Sleeps 8.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** This canal-front 4BR/3BA home sits just minutes from the beach for sunny days on the sand. Stretch out in 2,368 square feet of welcoming living space and kick back by the sparkling heated pool and spa in your private backyard retreat. After fun-filled days on the sand, enjoy a home-cooked meal alfresco on the lovely screened porch. Bring a boat to tie to the private dock -- there’s even room for boat parking on-site! LIVING AREA Unwind in the spacious living area, where ample seating offers room for the entire group to watch a movie on the 60” smart TV. A pool table provides hours of fun, and a breakfast table is perfect for family game night. KITCHEN & DINING Whip up tasty meals in the well-appointed kitchen, equipped with a full suite of stainless steel appliances as well as helpful gadgets and cookware. Keep the chef company at the kitchen bar for two. When it’s time to eat, gather at the table for six. BEDROOMS & BATHS This home sleeps up to eight guests in four bedrooms. Find comfort in the tranquil master suite, which boasts a king bed, 40” smart TV, and private access to the screened porch. The beautifully tiled en-suite bathroom is configured with a jetted tub and walk-in shower. The guest bedroom is fitted with a queen Murphy bed, while the guest bathroom is appointed with a tub/shower combination. A third bedroom offers a queen bed, 40” smart TV, and an en-suite bathroom with a tub/shower combination. Sleep soundly in the fourth bedroom, furnished with a queen Murphy bed and 40” smart TV. OUTDOOR AREAS Fire up the gas grill and dine alfresco for eight on the screened patio, equipped with a bench swing and 51” TV. Spend sunny days by the heated 6'-deep pool and spa in the lush backyard. Soak up the sun on multiple loungers or at a patio table for four. This canal-front home offers its own private dock, perfect for fishing or tying up a boat (up to 30’). EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi, a washer/dryer, and parking for four cars in the circular driveway. There is also space to park a boat or boat trailer. THE LOCATION This mid-Marathon home sits just minutes from the Crystal Coast for exciting days on the beach. To discover even more of the beautiful Florida Keys, take a scenic drive on the Seven Mile Bridge.
  • Luxurious Canal Home w/

    Key Largo: Vacation Rental
    3 BDR • 2 BA • Sleeps 7 • #246830
    215 to 220 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 rentals follow local/state tax rules. Each reservation includes applicable taxes, cleaning fee, and Property Damage Protection policy.
  • New Listing! Renovated

    Marathon: Vacation Rental
    3 BDR • 2.5 BA • Sleeps 10 • #252448
    217 to 520 USD/night
    Relaxation comes easy at this 3BR canal-side home, located in the private Yacht Harbor neighborhood in Marathon. This stylish home is full of coastal charm and offers a waterfront patio for grilling and entertaining. Minutes to the beach. Sleeps 10.. ** This home is professionally managed by Vacation Rentals, four-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With , you can always expect exceptional service, a high-quality experience, and one-of-a-kind accommodations. ** Relaxation comes easy at this 3BR/2.5BA canal-side home, located in the private Yacht Harbor neighborhood in Marathon. Recently renovated with all-new interiors, this stylish home includes two living areas, a screened patio, and a waterfront patio for entertaining and grilling. Get ready for an unforgettable coastal getaway; you’re just minutes from sugar-white sands and turquoise waters at this prime location! LIVING AREAS Brimming with natural light, the main living area has a beachy vibe that will quickly lull you into vacation mode. Spread out with a book on the sectional, or watch a movie on the 42” wall-mounted TV. Ocean blues add a splash of color to a second living room, furnished with a comfy sectional and a coffee table surrounded by wicker chairs. KITCHEN & DINING A contemporary kitchen impresses with sparkling marble countertops, glossy white cabinetry, and a full suite of stainless steel appliances. When it’s time to eat, a wooden dining table seats eight. BEDROOMS & BATHS This house sleeps up to 10 guests between three bedrooms. Comfort awaits in a spacious master bedroom, outfitted with a king bed and 50" wall-mounted TV. A stylish en-suite bathroom features a walk-in shower. A tranquil second bedroom has two full-size beds, while the light and airy third bedroom features a queen bed. Both bedrooms have a 40" wall-mounted TV. The guest bathroom is configured with a tub/shower combination. An additional half bath provides added convenience. EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi, cable TV, and a washer/dryer. Parking is provided for four cars in the driveway (including one covered space). Street parking is also available on a first-come, first-serve basis. OUTDOOR AREAS A screened patio at the rear of the home offers a relaxed social space, with a pair of loungers and a high-top table for four. Just beyond, you can soak up the sun on a private waterfront patio. There’s plenty of seating to kick back with a drink — whip up your favorite at the outdoor wet bar! Fire up the gas grill and dine alfresco at the patio table for four. THE LOCATION This coastal retreat offers easy access to dreamy beaches, with a prime spot between the Atlantic Ocean and Gulf of Mexico. Spend a morning kayaking, jet skiing, boating, and swimming in warm turquoise waters. Later, dig your toes into the sugar-white shores of Coco Plum Beach (2 miles) or Sombrero Beach (4.4 miles). Spot wildlife and learn about local history at Crane Point Hammock & Nature Trail (3.6 miles). Animal lovers will want to visit the Turtle Hospital (5.2 miles); this non-profit rehabilitation center offers guided tours and opportunities to feed its permanent turtle residents.
  • Canal-Front 3BR w/ Private

    Marathon: Vacation Rental
    3 BDR • 2 BA • Sleeps 6 • #241322
    243 to 701 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.

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