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
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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 Credit Card Star Rating
    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.
  • Located around the Corner
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    Located around the Corner

    Key West: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #239593
    298 to 665 USD/night Credit Card
    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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  • Islamorada Luxury Condo with 50' Private Boat Slip
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    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!
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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 139 USD/night 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
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    Across the Bay from

    Islamorada: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241141
    373 to 390 USD/night Credit Card
    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.
  • Escape to this 2br
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    Escape to this 2br

    Marathon: Vacation Rental
    • 2 BDR
    • 1.5 BA
    • Sleeps 6
    • #241101
    126 to 465 USD/night Credit Card
    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!
  • This Newly Remodeled 3br
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    This Newly Remodeled 3br

    Marathon: Vacation Rental
    • 3 BDR
    • 2.5 BA
    • Sleeps 8
    • #244891
    282 to 919 USD/night Credit Card
    This newly remodeled 3BR home boasts floor-to-ceiling ocean views in every room. Launch a kayak from the oceanfront yard, or hop on the provided bikes to explore the area. A nearby clubhouse offers a pool, hot tub, and private beach. Sleeps 8. Boasting stunning floor-to-ceiling water views in every room, this newly remodeled 3BR/2.5BA home promises a delightful oceanfront stay in the Florida Keys. A large patio provides ample seating and covered al fresco dining, while a private yard offers instant access to the clear blue waters. Launch one of the provided kayaks for fun-filled explorations, or hop on the bikes to cruise the surrounding area. You’ll also enjoy quick access to a nearby cabana club, complete with a sparkling pool, hot tub, poolside concession and bar, and a private beach. Renowned local attractions and adventures are also close at hand, including Crane Point Museums & Nature Center, Island Hoppers Aerial Adventures, and Captain Hooks Marina. LIVING AREAS This beautifully appointed oceanfront home features an open floor plan with abundant natural light, hardwood floors, and modern decor. In the living area, a leather sectional sofa accommodates seven in front of the 55” flat screen TV. An adjoining sunroom offers a cushioned wicker sofa and matching love seat -- a great spot to kick back and take in the incredible vistas. KITCHEN & DINING Sharpen your culinary skills in the well-equipped kitchen, complete with a full suite of stainless steel appliances - including a five-burner stove and a side-by-side fridge. When it’s time to eat, savor your creations at the breakfast bar for four, or gather at the five-person dining table. BEDROOMS & BATHS This single-story home sleeps up to eight guests in three bedrooms, each offering beautiful ocean views and direct access to the patio. Find quiet privacy in the master bedroom, replete with a king bed, 50” TV, and an en-suite bathroom with a walk-in shower. Both guest bedrooms have two queen beds, one of which includes a 50” TV. Across the hall, the guest bathroom is configured with a tub/shower combination. Providing added convenience, a half bathroom is situated just off the kitchen. OUTDOOR AREAS With gorgeous ocean views and comfy seating, the patio is a fantastic spot to unwind after a sun-soaked day. Fire up the gas grill and enjoy dinner outside. Play a game of outdoor shuffleboard on your very own court. As evening falls, gather around the fire pit and roast marshmallows under the stars. EXTRA AMENITIES Two kayaks and two bikes are available for guest use. This pet-friendly home also includes complimentary Wi-Fi, cable, a washer/dryer, beach gear, and parking for up to two cars in the driveway. (Please note that this property doesn’t have a dock or on-site boat parking. Kayaks can be launched via a small seawall. Bicycle availability is subject to any maintenance issues.) THE LOCATION Within a 9-minute drive, you’ll have quick access to the sparkling pool, hot tub, and private beach at the nearby cabana club. For more local excursions, Crane Point Museums & Nature Center, Conch Air, and Island Hoppers Aerial Adventures are 2 miles away, while Captain Hooks Marina & Dive Center and the Florida Keys Country Club are within 3 miles. 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 the 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
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    Take in Ocean Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #241694
    236 to 449 USD/night Credit Card
    Take in ocean views from the expansive rooftop deck of this 3BR/3BA Marathon home, featuring a master suite with new king bed and private deck. Make use of the complimentary bicycles and complex pool, and enjoy free membership to the Cabana Club. Sleeps 8.. Take in ocean views from the expansive rooftop deck of this 3BR/3BA Marathon home for eight. Your spacious master suite includes a new king bed and private deck. Spend time enjoying the sublime Florida weather on your covered patio and two-story deck. Pedal around the neighborhood on the bicycles provided and cool off with a refreshing dip in the complex pool. The home is located directly across the street from the boat house, where you can store and launch your boat for a fee. Plus, enjoy free membership to The Cabana Club beach and pool. ABOUT THE HOME Cool tile flooring flows throughout the open-concept living area, featuring exposed wood beams and floods of natural light. Settle onto the comfy sectional sofa with seating for five, and catch your favorite shows on the 46” wall-mounted flat screen TV. Whip up brunch in the granite kitchen with stainless steel appliances. Sip morning coffee at the breakfast bar for two, or gather for full meals at the glass dining table set for six. After a fun-filled day at the beach, fire up the grill on your covered patio, and dine alfresco at the table for four. The shaded porch swing offers a lovely spot to sit and read. Move to the upper deck with open-air dining for seven, or ascend the spiral staircase to your private 700-square-foot rooftop deck with outdoor shower. Soak up the Florida sunshine from two chaise loungers, or relax in the shade with a refreshing drink in hand. Whichever seat you choose, breathtaking ocean views are on full display. In the evenings, rest up in three spacious bedrooms with their own private bathrooms. The king-size master suite boasts a large walk-in closet, a 32” flat screen TV, and a private balcony with hammock chairs and a bistro table for two. Your en-suite master bath is configured with a walk-in shower and luxurious jetted tub. In the second bedroom, drift to sleep in the queen-size bed, watch your own 32” flat screen TV, and wake each morning to refresh in the en-suite bath with tub/shower combination. Upstairs, the third bedroom offers two twin beds, ample closet space, and a 37” flat screen TV. Next door, the third bathroom is equipped with a walk-in shower. Extras at this vacation home include complimentary Wi-Fi, Netflix, a washer/dryer, beach essentials, two bicycles, and parking for two cars under the house. THE LOCATION During your stay at this Marathon vacation rental, pedal around the neighborhood on the bicycles set aside for you, and cool off with a refreshing dip in the oceanfront complex pool. For a small fee, store and launch your boat at the Boat House across the street, and spend leisurely afternoons cruising on the water. Drive 4 minutes to The Cabana Club in Key Colony Beach, where you’ll have free member access to the private beach and pool club. Recline poolside at The Cabana Club Island Bar & Lounge, a local favorite for tropical cocktail specials. Treat yourself to dinner at the Island Fish Company, and enjoy seafood classics at a waterside table (only an 8-minute walk from your door).
  • Perched on the Largest
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    Perched on the Largest

    Marathon: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 10
    • #240137
    293 to 753 USD/night Credit Card
    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.
  • Newly remodeled home in
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    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3.5 BA
    • Sleeps 8
    • #242078
    399 to 949 USD/night Credit Card
    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.
  • Enjoy a Fabulous Adventure
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    Enjoy a Fabulous Adventure

    Marathon: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 8
    • #245109
    171 to 602 USD/night Credit Card
    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!
  • Enjoy Access to the
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    Enjoy Access to the

    Marathon: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 8
    • #243237
    155 to 423 USD/night Credit Card
    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!
  • All Photos, Amenities, Calendar,
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    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #241322
    149 to 701 USD/night Credit Card
    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.
  • Newly remodeled home in
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    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3.5 BA
    • Sleeps 8
    • #242079
    399 to 949 USD/night Credit Card
    Newly remodeled home in The Florida Keys with 3 bedrooms and 3.5 bathrooms. Located within a private yacht club with boat slips available for rent as well a centrally located clubhouse and pool area complete with top-notch amenities.. Marlin Bay Yacht Club is a newly remodeled private community located within Marathon, Florida in the heart of The Florida Keys. As you drive through the elegant gates of the property you are welcomed by an exquisitely decorated 2-story clubhouse. As you enter the clubhouse you are greeted by our accommodating concierge team who is more than eager to assist you in planning a trip of a lifetime. The clubhouse features numerous amenities for you to enjoy during your stay, including a full-service bar, a state-of-the-art fitness center, a yoga studio, sauna, steam room, billiards, shuffleboard, multiple big screen TVs, and beautifully appointed lounges for you to relax and spend time with your family and friends. As you walk through the clubhouse and step outside you are immediately taken back by the incredible views that The Keys have to offer. Here you will find a lovely lagoon style pool, a relaxing whirlpool, modern lounge furniture to enjoy the warmth, and a full-service tiki bar. Beyond this remarkable resort-like atmosphere we also feature a private 99-slip marina complete with an experienced dockmaster to prepare you and your vessel for an amazing sea excursion. Even if you do not plan to boat during your time with us, the clubhouse, the pool area and the dramatic 3-story residences are certainly designed to please all guests and provide you with luxury accommodations. Our 3-bedroom homes are fully furnished, professionally decorated, and feature an open floorplan. As you enter the ground floor from your 2-car garage you will find a lovely master bedroom complete with its own full bathroom and private patio. As you ascend onto the second floor you will find a state-of the-art gourmet kitchen which seamlessly flows into modern dining and living areas. On this level you will also find another private deck overlooking the beautifully landscaped pool area and a conveniently placed half bathroom. Last but not least, as you arrive on the third floor you will discover an additional master bedroom complete with its own full bathroom, wet bar, and private balcony. The third bedroom is also located on this level with 2 twin beds and a private bathroom as well. If the multiple levels concern you, there is no need to worry as our homes include elevators so you can easily access each floor.
  • Soak in Water Views
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    Soak in Water Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #238859
    147 to 416 USD/night Credit Card
    Soak in water views on the sun-kissed rooftop terrace of this 3BR/3BA home. Enjoy a master suite oasis with luxurious jetted tub and private deck. Keep your boat at your fingertips with plenty of dock space for rent nearby. Sleeps 8.. Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat nearby at one of the many spots available for rent, and then stroll back to the house to rest and recharge. You’ll feel on top of the world as you gaze over the clear waters of Florida Bay from the comfort of your 700-square-foot rooftop terrace, furnished with plenty of comfortable chairs, sofas, and recliners. End your day in the tranquil master suite. After a glass of wine or a nightcap on your private balcony, enjoy a soak in the jetted tub or a movie on the flat screen TV. ABOUT THE HOUSE For the ultimate movie night, gather your group in the spacious living area on the second floor and play your favorite films on the 55” flat screen TV. A sofa and love seat offer seating for five. Discerning chefs will appreciate the kitchen’s stainless steel GE appliances and dishwasher. Enjoy meals at the dining table for six or on the balcony with views of the neighborhood. Unwind in the first-floor master suite with a queen bed, walk-in closet, and 40” TV. The en-suite bath will be your oasis; rinse off in the walk-in shower or soak in the jetted tub. The private deck with a bistro set is perfect for enjoying coffee or a romantic cocktail for two. The second bedroom, located on the first floor, includes two twin beds, a 26” flat screen, and an en-suite bath. On the second level, the versatile third bedroom contains a queen bed and a queen-size futon to use as seating or sleeping accommodations for two. On the second-floor balcony, you’ll find a spiral staircase leading to your expansive private roof terrace. Lounge on recliners and soak in the sun, or gather your group in the shaded seating area to enjoy games, conversation, and panoramic bay views. Plan a barbecue on the shaded patio beneath the house, equipped with a gas grill and a dining area for eight. Two parking spaces are available, and you’ll find a washer/dryer on the first floor. THE LOCATION Take advantage of well-kept shared amenities. Lounge by the pool and enjoy sweeping bay views while you swim, or head down to the docks, where boat owners can rent bayside space to store their vessel. Idyllic Sunset Park Beach is just a 5-minute drive from your door. Florida Keys Aquarium Encounters, less than a half mile away, is perfect for a family-friendly afternoon of snorkeling and discovering marine life.
  • This 4br/3ba Key Largo
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    This 4br/3ba Key Largo

    Key Largo: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 6
    • #242718
    367 to 588 USD/night Credit Card
    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.
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    All Photos, Amenities

    Key Largo: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 7
    • #246830
    215 to 230 USD/night Credit Card
    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.
  • Enjoy a Sublime Location
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    Enjoy a Sublime Location

    Marathon: Vacation Rental
    • 4 BDR
    • 4 BA
    • Sleeps 8
    • #246154
    306 to 851 USD/night Credit Card
    Enjoy a sublime location directly on the Gulf of Mexico at this updated 4BR/4BA Marathon home — boasting gulf views and the best sunset views in the Florida Keys. Gorgeous private pool, entertainer’s kitchen, and a spacious sunroom add to the luxury.. Offering an unbeatable location directly on the Gulf of Mexico, this updated 4BR/4BA Marathon home comes with dreamy gulf views, and some of the best sunset views in the Florida Keys. Admire the stunning coastal views from a beautifully landscaped private pool, or the privacy of your spacious sunroom. The house also features a sleek kitchen with stainless steel appliances, a master bedroom with a plush king bed, and three guest bedrooms with comfy queen beds. LIVING AREAS Grand vaulted ceilings soar above an open-concept living space, with tons of room for your group to socialize. Sprawl out on a huge sectional couch to enjoy movie nights on the 60” flat-screen TV. In the mornings, enjoy breakfast in the sunroom. A glass top table seats four, and the views across the gulf are incredible. It’s also a fabulous spot for sundowners, with cushioned chairs to sit and admire the coastal scenery. KITCHEN & DINING The living room opens to a spacious entertainer’s kitchen with sparkling white granite countertops. There's a full suite of stainless steel appliances, including a French door refrigerator. A large kitchen bar seats four, and four more can sit at the nearby breakfast table. On the opposite side of the living space, another dining table seats six. BEDROOMS & BATHS Each of the stylish bedrooms are awash with light and coastal colors. A spacious master bedroom comes with a king bed, 50" flat-screen TV, balcony access, and an en-suite bathroom with double vanity, a walk-in shower, and a separate soaking tub. The second guest room offers a comfy queen bed. The third guest room is outfitted with a queen bed and a 42” flat-screen TV, while a fourth bedroom has a queen bed, 32” flat-screen TV, and a private patio. Both rooms have their own en-suite bathroom with a mosaic-tiled walk-in shower. A guest bathroom with a stylish walk-in shower provides added convenience. OUTDOOR AREAS Chances are you’ll want to spend the whole day by the beautifully landscaped pool. Palm trees sway in the coastal breeze, and there’s a stellar view of the gulf. Enjoy alfresco dining around the four-person patio table. Or laze on a poolside sun lounger. In the evening, fire up the gas grill and enjoy some of the best sunset views to be found in the Florida Keys. EXTRA AMENITIES Additional home amenities include complimentary Wi-Fi, cable TV, and a washer/dryer. Driveway parking is available for four vehicles (or three cars and a boat trailer). THE LOCATION You’re just minutes away from a host of lovely beaches. Sombrero Beach (a 17-minute drive) is one of the prettiest spots, with sugar-white sands and palm trees aplenty. Drive 3 minutes to watch and interact with dolphins at Dolphin Research Center. Or drive 10 minutes to dive, snorkel, and feed the resident marine life at Florida Keys Aquarium Encounters. When dining out, check out the fabulous local seafood restaurants, including Sparky's Landing and Island Fish Company — both within an easy 10-minute drive. 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 the 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!

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