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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 5
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 9, 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed December 29, 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 11
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 28, 2015
    Everything you need, easy to get around island. Quiet, no view of water. Great place for the price. I would stay here again.
    4 of 5 stars Reviewed March 25, 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 stars Reviewed October 25, 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    1 / 13
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    • Porch
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    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 22, 2015
    Being a Florida local, I travel to Key West quite often for the past 13 years and have never had a better and more pleasant stay than at the Duval Balcony. The owner was waiting...
    5 of 5 stars Reviewed October 21, 2015
    We stayed here in July and it was just what we were looking for. Pretty roomy for Key West, very clean and well kept, and right on Duval St. When we wanted to go out to eat, drink...
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    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 week ago
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service to...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    • ?
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    • x
    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $680
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    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Yard
    • Secure Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $541
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    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
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    • Private Outdoor...
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    • Pet-friendly
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    • Child-friendly
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    • x
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    • Elder access
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    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 35
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $199
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    • Internet Access
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    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    $405
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    • DVD Player
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    • Satellite TV
    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
    5 of 5 stars Reviewed December 15, 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
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    1 / 10
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $170
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    • Internet Access
    • Washer
    • Satellite TV
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 15, 2015
    The owners could not have been nicer. Clean, right downtown, close to all the action in town. Going to make it back and stay here again.
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $266
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    • Patio
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    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $270
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    • Washer
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    • Balcony
    • Parking
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed March 2, 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    $109
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    • Patio
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    • DVD Player
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $429
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $214
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    • Pet-friendly
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    • Child-friendly
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    • x
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    • Elder access
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    About this property
    'Island Wind' welcomes you to a sun drenched oasis in the heart of Old Town. Charming Bahamian style townhome with tin roof and white spindled porches reminiscent of Old Key West Just a block off Duval Street at the corner of Truman & Simonton in Windward Park a gated community consisting of 13... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Child-friendly
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    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
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    Key West, Florida Keys 33040
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    1 / 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $876
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    • Terrace
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    • ?
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    CORAL HAMMOCK Additional amenities include: close to pool, washer/dryer, stereo/cd/radio. View all property information
    Location Information
    Key West, Florida Keys
    1 / 54
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • Elder access
    • x
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    $1,100
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    • Pet-friendly
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    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • x
    • x
    About this property
    If only for a short time, gift yourselves the opportunity to experience life as a Key West yachter. This 42’ fully equipped blue water cruiser, docked at the Stock Island Village Marina affords you a “Dockside” overnight rate either before or after a scheduled Tortuga Sailing Adventure charter. A... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $214
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    • Washer
    • Terrace
    • Parking
    • DVD Player
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    7 day minimum please This fully furnished newly updated getaway is so close to all the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west (though parking space for one auto is available) Bike &... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 13, 2015
    My family loved this place! Cozy yet upscale furnishing and decor. Comfortable beds. Fully stocked kitchen. Very clean. And it was nice to have a washer and dryer. The location is...
    5 of 5 stars Reviewed March 5, 2015
    This place is more than a "touch" of Paradise. It's in a wonderful location. Beautifully decorated and came with everything we needed for our first Key West trip. Kitchen was...
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    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $17
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    • Waterfront
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
    • x
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    About this property
    I am happy you found this great Ocean View stay! Love to answer your Questions-fast- don't lose your dates just phone hurry! Scuze’ for site inconvenience. Because of variables happy to discuss anything further on this [by phone only] 3 blocks from Duval st. OCEAN VIEWS GALORE! although Not A... View all property information
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    Key West, Florida Keys 33040
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $299
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    • Child-friendly
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    About this property
    * This vacation home is available to rent on a monthly basis only * Dating all the way back to 1884, this delightful 3BR home is located in Bahama Village, part of Key West's prominent Old Town neighborhood. This single-family home is available to rent on a monthly basis. If you'd like more... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $457
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has to offer, as well as... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 28, 2014
    We were told about this magnificent property by very good friends. The location is in a quiet residential area, but it is easy to access all the activities of Key West. The...
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    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 4, 2013
    We have been renting a condo at this property for many years under different mangement companies and the folks managing it now are top notch the are doing a great job
    4 of 5 stars Reviewed July 31, 2013
    The location was perfect for us since we had a boat and the rental came with a boat slip. Our balcony even looked down on our boat. Room space was very adequate for the eight of...
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    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    MONTHLY RENTAL (minimum 28 days), called Secluded Casa, makes island living easy. It's a spacious, warm, and inviting one bedroom unit in a four unit building, much larger than many other one bedroom homes in Key West. The home is located in the Casa Marina District close to Higgs Beach on the... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    5 of 5 stars (36) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    $325
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    • Pet-friendly
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    5 of 5 stars Reviewed December 18, 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
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    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $349
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    • Satellite TV
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    About this property
    Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2016! Max occupancy: 2 couples or 1 couple with up to 3 children under 12. The calendar on this site shows availability. We do not take partial weeks or bookings of less than 7 nights unless it is between... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    5 of 5 stars (27) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 30, 2015
    We loved our stay at Casa del Sol. The location was perfect for sight seeing and walking everywhere. We never used our car for the week's stay. The beds were comfortable, the...
    5 of 5 stars Reviewed August 31, 2015
    Casa del Sol is in a perfect location in Key West with an easy 2 block walk to Duvall Street but in a quiet relaxing residential area. The condo is very clean, well equipped and...
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    CORAL HAMMOCK Additional amenities include: sofabed, upstairs unit, washer/dryer, stereo/cd/radio, end unit. View all property information
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    Key West, Florida Keys
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Price and availability subject to change without change*** Situated on the Atlantic Ocean, the property captures Key West style with modern convenience. Conveniently located near Key West Int'l airport and only a short distance to beaches, shopping and more. A series of residential vacation... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 stars (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $300
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 13, 2015
    The actual unit was really nice and accommodating for us (a party of six). However, from the time of check in and a few times afterwards, the management official working at the...
    4 of 5 stars Reviewed January 24, 2014
    Nice location looking out on Garrison Bight Marina and close enough to Old Town. Super spacious unit was very nice and clean. Completely equipped and has washer/dryer stack. A...
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    1 / 22
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 5, 2015
    My Husband, I and my sister spent 6 days in Key West. This was a home like condo to stay in. It had a kitchen,dining room and living room on the main level with a bathroom(all one...
    4 of 5 stars Reviewed April 8, 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $239
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 22, 2015
    Traveled to Key West with my sister and my Mom to celebrate Moms 85th birthday. The house was so close to everything we wanted to do and see. The grocer nearby was great, the...
    4 of 5 stars Reviewed May 2, 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
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    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    You have use of one of four private cabins with a private marine style bathroom. Three cabins available for rent. You will share the common areas with new friends. The cabin is air conditioned with a queen like bed. Captain Charles and wife Deborah use one cabin. When conditions allow we offer a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 29, 2015
    Five of us stayed on the Anna B over the weekend. It is a very nice catamaran sailboat, clean and well maintained. Each stateroom had fresh linens, its own en-suite bathroom, and...
    5 of 5 stars Reviewed May 28, 2015
    Our stay was wonderful! It's was clean, quaint & relaxing! I hope to return soon. Captain Charles was a pleasure to speak to!
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $133
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    About this property
    OVERVIEW: Right in Key West -- NOT the upper keys. MONTHLY RENTAL ONLY. Swimming pool, Right on the water. Salt water fishing on location. Sea Kayaks on premises. Salt pond tours on premises. Swim with manatees on premises. Ping pong table. 7 doors down from Jimmy Buffett's old house. The... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $250
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    About this property
    'TEE BY THE SEA' vacation rental (we include 7 bikes free for our guests!!!) If you love...GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT...than you'll love 'Tee by the Sea'. We're less then 1/2 mile outside of Key West, located in Stock Island. We are 4 1/2 miles... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to the Duncan House - your home away from home in beautiful Key West. The Duncan house is a recently renovated private home with three bedrooms and two baths located in a quiet, Old Town, Key West neighborhood only 10 minutes to Duval Street and only 5-10 minutes to Smathers Beach. 3... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $193
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    About this property
    The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living for yourself. From its fabulous... View all property information
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    Key West, Florida Keys
    1 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
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    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 24, 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which also...
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    The master bedroom has a queen sized bed with a feather mattress topper to experience a floating cloud effect. It has cable flat-screen TV, DVD/VCR, and a balcony where you can sit (take director's chairs from bedrooms) for morning coffee or evening cocktails. The customized closet has a set of... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4 of 5 stars (37) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 15, 2015
    We stayed in this property for two days. We had a good time. Staff is friendly. They have everything what we need there. I read reviews about this property and some one mentioned...
    4 of 5 stars Reviewed December 11, 2015
    Nice location. Hot tub, patio nice, porch fun to watch traffic a passerbys with morning coffee. Houe is cute but needs a little TLC. Fingerprints on walls and doors, missing...
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West Vacation Rentals and Condos

    Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

    Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

    Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

    Where To Rent a Vacation Home in Key West

    Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

    Many House Rentals Near Attractions and Activities For All Ages

    Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

    Key West Bars and Restaurants

    Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

    Book a Key West Vacation Rental For Your Next Trip

    Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.