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 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.
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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

    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.
  • Soak in Water Views

    Marathon: Vacation Rental
    3 BDR • 3 BA • Sleeps 8 • #238859
    144 to 372 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.
  • Newly remodeled home in

    Marathon: Vacation Rental
    3 BDR • 3.5 BA • Sleeps 8 • #242078
    449 to 849 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.
  • Across the Bay from

    Islamorada: Vacation Rental
    3 BDR • 2 BA • Sleeps 8 • #241141
    390 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.
  • All Photos, Amenities

    Key Largo: Vacation Rental
    3 BDR • 2 BA • Sleeps 7 • #246830
    224 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.

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