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Elder Access Holiday Rentals in Key West

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    96 Matching Rentals in Key WestView all 420 rentals
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    Sunrise at Seaside Condo 2 Bedroom1 / 48
    (20)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (37)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Center of It All - Paradise Island Suite1 / 56
    (30)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 39
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Kathy and Bob have a great large two bedroom condo with generous resources; tv in each room, radios, games, wet bar, great space for cooking and lots of beach supplies: bikes...
    Reviewed 17 June 2017
    Everything with this rental was first rate from start to finish. Kathy, the owner, checked in with us multiple times in the weeks leading up to our arrival to make sure we knew...
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    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Condo close to the Ocean1 / 22
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
    Reviewed 22 November 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Florida Beachfront Condo1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2016
    Fantastic. No other word describes it better. The view, the amenities, the layout of the condo...all fantastic. Owner is a very nice lady too. Very easy to deal with. Will...
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    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    KWO - 2 BR/2 Bath, Private Pool, Separate Cottage1 / 23
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    Great location in Old Town, away from Duval Street, but still within walking distance to great restaurants and Duval if that's your idea of fun. The house has everything you...
    Reviewed 23 April 2017
    We had an amazing time in Key West and we were pleased with the rental. We would go back to Key West Oasis for our next visit.
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Shelleys Rooftop Hideaway1 / 15
    (5)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another...
    Reviewed 18 March 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...
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    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May1 / 17
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Satellite TV
    • Air Conditioning
    • Terrace
    • Secure Parking
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location!! Sunrise off Southard has it all! An upscale one bedroom home offers tropical beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 14
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed 14 July 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Truman Annex Shipyaard with Tropical Garden1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Garden
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    We love staying here. There was plenty of room and the condo was nicely decorated. We walked and biked all over with ease -- great location.
    Reviewed 15 May 2017
    Love love loved the town house. Beautiful. Love cation was perfect. Was able to walk most everywhere. Felt safe walking late at night also. Beautiful location. Can't wait to...
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    About this property
    Decorated in shade of sea foam and coral, this property is located in the Truman Annex and puts all of Key West's top attraction within easy walking distance. French doors open to a garden with hibiscus and cat palms framing a comfortable patio. Both bedrooms have queen beds, with a sofa bed in...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Mango Hideaway-King Suite just steps off Duval St1 / 18
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Grill
    • Private Garden
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    The Mango Hideaway is a nice spot in the middle of Old Town. Walking distance to everything. Private patio and entry off of the side street are a plus. Great location and a...
    Reviewed 4 March 2017
    We had a great time in Key West staying in the Mango Hideaway!Very private and comfortable yet only a minutes walk to Duval street.Also centrally located in old town so seeing...
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Terrace
    • Washer
    • Central Heating
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condominiums. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 BR (4bed) 2 BA Luxury Yacht-Sunset Cruise avail1 / 18
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2016
    We had such a great time staying on the Key West Yacht and Breakfast, It was definitely a different experience staying on a boat but we had such an amazing time. It was so...
    Reviewed 26 May 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places...
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    About this property
    Tourism permitted again starting Oct 1! Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tropical Escape1 / 26
    (84)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    This place is just perfect! Nice and clean, and check in was a breeze! But what I really loved about it is the location! You are in Key West, but you are far enough away from...
    Reviewed 7 July 2017
    Owners were great and very accommodating. The condo is beautiful. Has everything you need. Pool was great to use. We would rent again when we come to key West. We had a great...
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Catchin' Moments is a beautiful 82' Hatteras, located in Key West, Florida. She is docked at the best slip in Key West Harbor Marina. Stay fully accommodated with a four bedrooms/bathrooms, huge living area, large kitchen, outside dining area, and upstairs lounge. The marina has a pool with pool...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    KEY WEST LA BRISA CONDO - North Building1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Our party of 6 (2 adults, 2 boys ages 23 & 19, & 2 16 year old girls) rented this in July. Room was very well appointed. Everything we needed was provided. Well stocked...
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    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. Our condos' at La Brisa are two bedrooms with two full bathrooms on the third floor. The master bedroom has a king size bed with a walk...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LAST MINUTE DISCOUNT! 48' 4 Bed 4 Bath Yacht1 / 25
    (13)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    Renting the Bella Maggio is a unique experience. You stay aboard a luxury sailing yacht, with all ameneties one would ever need. The rooms are kept cool with A/C. The...
    Reviewed 5 days ago
    Great adventuring boat Watch for dolphins. Snorkeling,Views,Sun,fun,PalmTrees,Lifeisgood,tan,RoosticaIsVerygood,
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    About this property
    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class marinas giving you full access to its restaurant and private pool during your stay. Very spacious and warm with its galley...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oceanfront 2 Bedroom 2 Bath Condo Key West Florida1 / 17
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Sauna
    • Washer
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Our family of 4 returned from Key West yesterday after a wonderful vacation. The condo worked great for us - very roomy, clean, well-stocked with anything you might need while...
    Reviewed 8 March 2016
    The condo was great, had all the amenities! Perfect location, right across from the beach, beautiful view! Plus it wasn't far from downtown.
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    About this property
    The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Listing Family Friendly1 / 32
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2017
    Awesome condo. Perfectly placed near to the hustle and bustle of Key West yet far enough to be tranquil. Roy's condo has all the amenities of my home. Great kitchen, plenty of...
    Reviewed 7 March 2017
    The townhouse on Stock Island (Key West) met all of our needs. It was clean, roomy and convenient. Having 3 full baths was a real plus for 6 women. The pool was delightful...
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    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean Front View Every Room*90' Scenic Balcony WIFI IN KEY WEST NOT ISLANDS AWAY1 / 18
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Children's Pool
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 February 2017
    The property offered the most beautiful sunrise views to wake up in bed to! Every bedroom has sliding glass doors that open to the balcony overlooking the ocean and if you leave...
    Reviewed 24 February 2017
    This property is amazing. You wake up to your own private view of the ocean! I love how in this unit, unlike others you have complete privacy. The pool and hot tub are...
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    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West. 2200 sq. ft living area. This place is really incredible! it's one of the largest oceanfront suites in Key West. 3 bedroom, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Beautiful property. This house was stunning, thank you so much for letting us stay there. All amenities were provided. I love all the plants and trees surrounding the pool and...
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    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included.
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Ray with amazing view1 / 14
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    Tried something like this for the first time. Very satisfying experience overall. Will recommend to others.
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    About this property
    Enjoy Key West with a unique experience to remember forever. Your water home, a 35' Sea Ray, is a moored (heavy duty anchors) boat in Key West with an unobstructed view of the boats & harbor, stars, and beautiful water. Access is provided by a short water taxi ride. I will help to escort you to the...
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    Location Information
    Key West, Florida Keys 33040
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a luxury 43 foot yacht. Everything is first class. Full galley. Very clean. Brand new. Great friendly marina. Lots of artists and creative people work and live here. Great restaurant the Hogfish Bar and Grill is right next door. Six beds behind 4 doors and 2 baths. Three AC units....
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Housekeeping Included
    • Ocean Views
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT PENTHOUSE with LOFT - 2BR/2BA + GREAT VIEWS OF THE GALLEON MARINA, HISTORIC SEAPORT & OCEAN 5th FLOOR CONDO RENTAL / SLEEPS 8 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout / Available Jan 13-20, 2018 / EXCEPTIONAL LOCATION, CONVENIENCE & CASUAL LUXURY / On...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new stainless appliances including a mini-refrigerator,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Catamaran CALYPSO with Summerallthetime Sailing Co1 / 31
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2017
    We had the pleasure to sail around the Florida Keys on the Calypso last month. The boat was great and very well kept. Beds were comfortable and cabins felt clean and polished...
    Reviewed 27 March 2017
    Capt John took our family of 4 on an ultimate Spring Break Keys journey!The sailboat is well equipped and very clean and modern. We had plenty of room to rest and play on...
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    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southernmost Retreat- 1 Block from Duval1 / 99
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2017
    This is a nice spot right of strip. Place is more for a family w young kids. Third bedroom is kinda small. Other than that place was real confronting. Enjoyed how close to...
    Reviewed 9 November 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
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    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 bedroom Condo Presented Key West Style1 / 28
    (127)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I had booked this condo months before and had great responses from Pamela. Our arrival times was Sunday September 10th. We were leaving Houston ( Hurricane Harvey...
    Reviewed 19 August 2017
    The Condo in Key West was awesome!! It has a balcony with a view of the beautiful pool. The condo was well equipped and immaculately clean. It is convenient to all of the...
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    About this property
    This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West 2bd/2ba Condo - Monthly1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West is like a little piece of the Caribbean at the lowermost point of the United States: it’s reliably warm, the waters are a gorgeous turquoise, and it is a small, intimate community. From this second floor condo it’s just a short walk to Mallory Square’s sunset celebrations, the Ernest...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Central Heating
    • Washer
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    • Waterfront
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM RENTAL REQUIREMENTS due to licensing restrictions; rates go down the longer you stay; deals and specials offered. Quiet end unit located in the Truman Annex. Just steps away from Fort Zachary State park/beach; two blocks from Duval Street and one block from The Green Parrot. Walking...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Top Of Duval- 6 Bedroom Penthouse1 / 27
    (10)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Washer
    • Grill
    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    • Outdoor Dining Area
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2017
    Top of Duval is centrally located in town which made it perfect for walking to restaurants and bars and to see the suset at Mallory Square. We rented all 6 of the suites and...
    Reviewed 30 June 2017
    We stayed in this location first in 2008 and it was an incredible experience. We did it a few years in a row until the ownership changed and it was hard for us to find it. I was...
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...
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    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Sailboat Camping 4 The Adventurous!1 / 15
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pearson Sloop anchored only a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing penthouse condo has one of the best view in Key West. Located in historic Mills Place in the main part of Truman Annex, you have the views of the Gulf and ships that pass by the windows as they arrive and leave port. The apartment has four exposures and three of them with balconies....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Banana Key1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Terrace
    • Air Conditioning
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    • Satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2017
    Truman Annex is a great location with access to all old town amenities. Pool areais great and neighbors are friendly. Condo was recently sold & new owner is planning on...
    Reviewed 27 June 2015
    Great place and nice location to Mallory Square. Not too far of a walk to Blue Heaven which is a must. The pool was very nice and very clean. The Banana Key is a great condo...
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    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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