Key West Vacation Rentals by Owner

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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Key West last minute deals on vacation homes will be highlighted in red if available. Start your accommodation search in Key West now. Just enter your travel dates, number of travelers, and click 'search' for a list of properties for rent.

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  • On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #69125
    avg $288 USD/night Credit Card
    1350sq. ft. of fabulous living space located in a ocean front condo on the 2nd floor. Garden and partial ocean view from a 38ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. The property is decorated and managed / maintained by me personally assuring you of a memorable vacation in a property that is way above the average investor owned rentals offered by management companies. The average temperature is 77.8 degrees, making Key West the warmest city (average temperature) in the United States. It has never been below 41 or above 98 degrees.
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  • Islamorada Luxury Condo

    Islamorada: Bay Harbour: Condo in a gated community
    • 2 BDR
    • 3 BA
    • Sleeps 6
    • #209708
    avg $239 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.
  • This beautiful condo is on

    Key Largo: Moon Bay Yacht and Tennis Club: Condo in a complex
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #13373
    avg $161 USD/night Credit Card
    This beautiful condo is on the fourth floor. There is an elevator in the building. Being on the fourth floor makes for a spectacular view from the screened in porch, living room, dining room, and master bedroom. Ceiling fans. Moon Bay has everything you need for a great vacation. There are free tennis courts, pool, saunas, a private boat slip,basketball hoop, and a dock for fishing and swimming to mention just a few of the amenities. There is a recreation room with ping pong and a water front grill. Wireless Internet.
  • Paradise in Marathon in

    Marathon: House
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #203104
    avg $219 USD/night Paypal
    Diving, swimming and fishing all minutes from your private dock & garden patio, in the heart of the beautiful Florida Keys, 45 minutes to Key West & 15 minutes to one of the worlds few living reefs. This large private home has all the needs and comforts of home and then some, just bring your tooth brush. From the 6 person Hot Tub to the 42" DLP HD T. V, to walks on the world famous 7 Mile Bridge. No need for clocks here...You are in Paradise. Less than 10 miles to 3 State Parks an 1 mile to town Large Master bedroom with King Bed & Private Bath and tumbled marble double vanity. Sun Room with water view and Large Patio Set for your relaxation with lighted dock for night fishing. Fish from your private 50' Dock or Take a Dive at Sombrero Reef. Less than 15 min away.

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