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... read more
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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  • 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.
  • Buttonwood Bay Condo

    Key Largo: Condo
    3 BDR • 2 BA • Sleeps 4 • #256212
    171 to 186 USD/night  
    Beautiful bright and remodeled Buttonwood Bay Condo. It's one of the few 3 bedroom with 2 full bath units for rent in the community. No stairs inside the unit. It is a spacious corner unit with a 2000 sq ft single floor plan. Located close to the tennis courts and pool. Our home has new furniture and all new kitchen appliances. From the moment you enter the apartment you enjoy a beautiful view. It's the perfect place to sit back and relax. The master bedroom has a queen bed and a spacious private full size bathroom with double sinks along with a large shower. The master bedroom has his and hers walk in closets. The second bedroom has a queen size bed and plenty of closet space. The third bedroom has a trundle bed and a television. The second renovated bathroom has tub/shower and modern glass sink. The kitchen features all new appliances and is fully equipped. The dining table seats 5 and the kitchen bar seats 3. The relaxing and beautiful view of the waterway is fully visible from the living room and partly from two of the bedrooms. Enjoy sitting and relaxing on the large comfortable leather couch. The views are amazing. You can open the wall to wall glass sliding doors and bring the outside in as you feel the sea breeze. From the unit you can see manatees, tarpon or even porpoises. Enjoy the morning light as you sip your coffee or the beautiful sunsets off the Martini Deck located very close to the unit. Our home is equipped with Wi-Fi. The coral rock boat dock is adjacent to the building and a few steps to the Florida bay. In addition to the very rare sandy beach, the community of Buttonwood Bay has: - 3 heated pools - 5 tennis courts - a renovated clubhouse - a basketball hoop - a volleyball court - a game room - a library - a newer fitness center overlooking the marina - saunas - an observation deck - several sunset decks throughout the bay - Boat launch - large boat slips that may rented Buttonwood Bay has a 24 hr manned gate-house and security patrol throughout the private 42 acre community. There are many places to visit such as John Penne Kamp Coral Reef State Park, Everglades National Park, and all the other islands leading to Key West. There are many fun things to do like fishing, swimming with the dolphins and feeding the tarpon at Robbies. You'll also have excellent dining choices from casual to fine dining located nearby. We welcome you to our special home away from home and know you will love it
  • Executive Bay 2 / 1.5

    Islamorada: Executive Bay Club: Townhouse in a gated community
    2 BDR • 2 BA • Sleeps 4 • #234599
    140 to 140 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.
  • Marlin Bay Resort & Marina

    Marathon: Vacation Rental
    3 BDR • 3.5 BA • Sleeps 8 • #242079
    399 to 1,049 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.
  • Marlin Bay Resort & Marina

    Marathon: Vacation Rental
    3 BDR • 3.5 BA • Sleeps 8 • #242078
    429 to 1,049 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.
  • Bayside 3BR/3BA w/ Heated

    Marathon: Vacation Rental
    3 BDR • 3 BA • Sleeps 8 • #238859
    283 to 424 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.

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