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Holiday Rentals in Key West, FL

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    €174
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    1 / 13
    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    €263
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    1 / 11
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €194
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    1 / 5
    3 of 5 stars (1) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €461
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    1 / 7
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
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    €858
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    1 / 14
    2 Bedrooms / 5 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Washer
    • Wi-Fi
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    • Suitable for children
    • ?
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    • x
    About this property
    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
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    €376
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    1 / 22
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Pets allowed
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    About this property
    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
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    5 of 5 stars Reviewed 5 March 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
    5 of 5 stars Reviewed 28 January 2015
    Loved our stay at toon hall. Awesome home away from home. Had all amenities we needed and location was great. Property was private and secure. Staff was responsive to...
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    €2,051
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    1 / 24
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Pool Table
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
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    €230
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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    €267
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    1 / 12
    4 of 5 stars (15) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining... View all property information
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    4 of 5 stars Reviewed 24 January 2013
    We spent 2 weeks at this condo, it was beautiful. We were right on the ocean and spent numerous hours on the large lani. The condo was very roomy and well kept. Our only problem...
    3 of 5 stars Reviewed 2 July 2012
    Going downtown to pick up the key at the rental place was a major pain, and we had to set there for a long while before someone even acknowledge us. The beach club #204 should of...
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    €1,383
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    1 / 6
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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    €3,502
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    1 / 15
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows... View all property information
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    4 of 5 stars Reviewed 6 February 2013
    We really loved the cottage and did appreciate all the little extras our host had provided. The location couldn't have been more convenient. We rented bicycles but could have...
    5 of 5 stars Reviewed 26 June 2009
    I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and...
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    €4,952
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's 'Guestbook' column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our... View all property information
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    5 of 5 stars Reviewed 8 August 2013
    Don't reserve at Olivia Cottage . . . because you may prevent us from doing so. We have traveled the world to just about every 5 star hotel of interest, and Olivia Cottage is the...
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    €1,383
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    1 / 11
    5 of 5 stars (40) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    5 of 5 stars Reviewed 25 June 2013
    Stayed at the Shipyard 253 and had a wonderful time. Very nicely decorated, comfortable and a great location - just 2 blocks from Duval St. I would stay there again!
    5 of 5 stars Reviewed 31 May 2013
    Great central location. Walking distance to most things of interest. Liked the fact it's a Gated community with assigned parking place. Not beach front, but that wasn't important...
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    €275
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of 4 exclusive units at Abbey Road, The original Cuban tile has been preserved throughout the house, wherever possible. Upon entering the spacious living room, a large tropical sectional queen sleeper sofa allows you to comfortably watch the 46” flat screen TV/DVD. Also available is an I-Pod... View all property information
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    5 of 5 stars Reviewed 30 March 2015
    This is my 5th time to Key West and by far the best place my friend and I stayed in. Previous stays had been hotels and sailboats. Very clean and secure and easy walking/biking...
    5 of 5 stars Reviewed 7 December 2014
    My spouse brought me to KW to celebrate my birthday, what a truly wonderful time we experienced on our entire trip. Lennon Lodge was absolutely cozy, comfortable, and private...
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    €277
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    1 / 20
    4.5 of 5 stars (18) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    5 of 5 stars Reviewed 18 July 2013
    I used to live in Key West and have had friends stay here before. I was excited to see the new renovations they had done. The room was beautiful and clean and our stay was great...
    4 of 5 stars Reviewed 2 November 2012
    We had a corner 2bed unit that was spacious. Kitchen was well equipped to accommodate 8. Helpful advice from office.
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    €127
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    1 / 27
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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    5 of 5 stars Reviewed 29 October 2014
    We have stayed in this lodging five times. It is very clean and service is excellent and friendly. The location is secluded and especially quiet.
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    €173
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    1 / 23
    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    The kitchen offers an under-counter fridge, microwave, coffee maker, toaster, blender and everything to cook, prepare and enjoy a light meal…and don’t forget the BBQ grill and Ice-maker by the pool! This very comfortable unit also has a very sexy two-person custom shower with glass door,... View all property information
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    5 of 5 stars Reviewed 30 June 2014
    The unit was clean and in a great location. Maintenance was attentive and cleaning staff also. The only trouble we had was virtually ever night some giant vehicle was running...
    5 of 5 stars Reviewed 4 April 2014
    The place we stayed at was small inside, but big on the outside space. The courtyard was beautiful and added another dimension to the space. Like a living room in the tropics!
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    1 / 24
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of Southernmost Sanctuary Suites The Osprey Suite (Formerly the Osprey Suite) - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a... View all property information
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    5 of 5 stars Reviewed 28 August 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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    4.5 of 5 stars (31) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    4 of 5 stars Reviewed 16 January 2015
    This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and walk...
    5 of 5 stars Reviewed 17 November 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a long...
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    €238
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    1 / 36
    4.5 of 5 stars (15) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features... View all property information
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    5 of 5 stars Reviewed 1 July 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
    5 of 5 stars Reviewed 4 February 2014
    We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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    1 / 25
    4.5 of 5 stars (15) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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    5 of 5 stars Reviewed 11 December 2014
    Amazing condo ! Great Staff ! Beautiful place with comfy beds and all the comforts of home and then some ! Hot Tub !!! Full kitchen w/washer and dryer. Gated parking and 2 pools...
    5 of 5 stars Reviewed 21 August 2014
    I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
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    5 of 5 stars (3) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park... View all property information
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    5 of 5 stars Reviewed 26 September 2014
    We felt grateful to have the opportunity to experience this historic home in Key West. It is conveniently located to restaurants and attractions. The home itself is beautifully...
    5 of 5 stars Reviewed 19 July 2014
    We were delighted when we entered this lovely house. Very "Key West," just what we were looking for. The house was clearly updated with high-quality finishes and in impeccable...
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    1 / 8
    4.5 of 5 stars (64) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (64) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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. Any reservation obtained under false pretense will be subject to eviction... View all property information
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    5 of 5 stars Reviewed 6 March 2014
    We had a wonderful time at this condo. The Condo was very large and comfortable. We were around a small corner from the elevator which really helped since I was the youngest at...
    4 of 5 stars Reviewed 13 November 2013
    Its very good Condo with ocean view scenic view. I had visited with my family and we like the condo very much it comes with fully equipped kitchen and is very comfortable and...
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    1 / 28
    4.5 of 5 stars (31) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and... View all property information
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    4 of 5 stars Reviewed 11 November 2014
    The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
    2 of 5 stars Reviewed 27 October 2014
    My friends and myself stayed at this house during the week of Fantasy Fest in October of 2014. The house was nice, but was too far from town to walk everyday. Next time we will...
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    4.5 of 5 stars (11) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork... View all property information
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    4 of 5 stars Reviewed 27 January 2015
    First things first - this property is a great value for the Keys. Craig in the office was extremely friendly and helpful. Booking the reservation was quick and easy. They...
    5 of 5 stars Reviewed 13 February 2014
    We stay at the Palm Isle on White Street every year, and love it! It's perfectly close to everything in Old Town Key West, as well as the beaches. You can walk most places, but...
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
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    5 of 5 stars Reviewed 13 October 2014
    The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
    5 of 5 stars Reviewed 25 July 2014
    I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveller have booked this property
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    • Air Conditioning
    • Grill
    • Gym
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with... View all property information
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    4 of 5 stars Reviewed 19 January 2015
    Great location; we loved having the back gate for direct access out to Angela Street and the close proximity to the Green Parrot and Blue Heaven - two of our Key West favorites...
    4 of 5 stars Reviewed 15 January 2014
    Love Key West and staying at the Shipyard condominiums put us right with in walking distance to every thing we love to do. We have been to Key West four times in four years and...
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    4 of 5 stars (37) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
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    5 of 5 stars Reviewed 26 January 2015
    Wonderful property, great location for walking around Key West. Rooftop deck for morning coffee and enclosed patio. Parking is at a premium, especially around the property, so...
    5 of 5 stars Reviewed 4 November 2014
    My wife and I stayed at the Sunset Suite - Nightly which is managed by Key West Vacation Rentals. This was our first trip to Key West as we went for the Meeting of the Minds. We...
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    4.5 of 5 stars (3) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house.... View all property information
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    5 of 5 stars Reviewed 29 July 2014
    Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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    5 of 5 stars (8) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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    5 of 5 stars Reviewed 9 March 2015
    We loved our stay at Catherine St. The home is set up with everything that you could ever need. The pool is very private. Skinny Dipping a definite. All of the furniture is custom...
    5 of 5 stars Reviewed 26 February 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
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    4 of 5 stars (30) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
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    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    About this property
    Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and... View all property information
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    5 of 5 stars Reviewed 18 April 2014
    This house will not be for everyone. It's rustic, and advertised as such. If you like new, bright, cookie cutter houses with granite countertops and pillowtop mattresses, with...
    5 of 5 stars Reviewed 22 August 2012
    The house was even more perfect than we'd imagined. It perfectly captured the Key West charm that we wanted while visiting. The backyard was amazing and we enjoyed the pool and...
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas.... View all property information
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    5 of 5 stars Reviewed 4 May 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    4.5 of 5 stars (20) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was... View all property information
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    5 of 5 stars Reviewed 15 May 2014
    Everything was just perfect! We couldn't have dreamed up a better place to stay. It was so comfortable and accommodating, not to mention ... soooo Key West! We loved it! Thank you...
    4 of 5 stars Reviewed 5 November 2013
    the best feature is the patio. everything else is good too. great location - quiet - wifi works - tim at historic hideaways is great to work with.
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    4.5 of 5 stars (22) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Gym
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
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    2 of 5 stars Reviewed 12 August 2014
    Overall the unit was nice. A few rips in the living room chair; could use recovering. The kitchen had all the amenities and we lacked for nothing. The master bedroom was very...
    5 of 5 stars Reviewed 6 August 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry detergent Traveled...
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
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    4.5 of 5 stars (24) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Grill
    • Gym
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    4 of 5 stars Reviewed 25 March 2015
    Had a great time in Key West and this place made it all possible! First of all, it is within a block or two of Duval St. Staying that close was important to us because we wanted...
    5 of 5 stars Reviewed 24 October 2012
    We loved this place. We travel with out camper but thought staying in old town would be a good choice. We were right. We stored the camper and parked the van (one of the few...
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    4.5 of 5 stars (28) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
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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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    5 of 5 stars Reviewed 8 May 2013
    Great place for singles And families. Easy access to entertainment and even Publix, Walgreens, restaurants everything! staff great, Highly Recommend! gorgeous view
    1 of 5 stars Reviewed 30 April 2013
    We have been going to Pelican Landing for the past several years. This has been the best experience so far. Any concerns we had were addressed immediately and the pool looks great...
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    4.5 of 5 stars (50) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Gym
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    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
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    4 of 5 stars Reviewed 16 December 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You will...
    5 of 5 stars Reviewed 25 July 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story 'cottage' offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living... View all property information
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    5 of 5 stars Reviewed 18 January 2015
    My wife & I have been to Key West a few times, and this last trip we brought some first timers with us. We stayed at the Pineapple Cottage and it was amazing. It truly is a...
    5 of 5 stars Reviewed 28 January 2014
    This place is amazing. I have been to Key West numerous times and it is rare to find a place so perfectly located in the Old Town area that also has the privacy and feeling of...
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    3 of 5 stars (5) Average
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex. Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of... View all property information
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    4 of 5 stars Reviewed 14 July 2014
    Coral Cove was a great place to stay for 2 people. We only stayed for one night, which was just enough. It was a little cramped, but was a safe and comfortable place to sleep. It...
    2 of 5 stars Reviewed 2 June 2014
    We stayed for 3 nights. Yes it's small, but tiny describes it better. I have never had back problems with all the traveling I've done, until now. The worst bed. Extremely cheap...
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    4 of 5 stars (5) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million... View all property information
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    4 of 5 stars Reviewed 25 November 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St. Everything...
    5 of 5 stars Reviewed 7 February 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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    4.5 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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. Eaton Manor sits on the north side of LaBrisa and provides easy access to... View all property information
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    4 of 5 stars Reviewed 14 May 2013
    Overall the condo is very nice. Towels and sheets could use an update along with all of the kitchen amenities. Mainly pots, pans, silverware etc. overall the place worked out...
    2 of 5 stars Reviewed 4 April 2013
    First off, we are not the type of people looking for a 4star place on a beer budget, then trash the accommodations on trip advisor because a lamp was out or the water tasted...
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    5 of 5 stars (27) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living... View all property information
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    5 of 5 stars Reviewed 7 December 2012
    The Queen Conch property is a very well maintained property and provides the perfect setup for a small gathering of friends or family. The main common areas are large enough and...
    5 of 5 stars Reviewed 5 December 2012
    Had a large party (8 adults) and this was just the right kind of property for our group with 3 separate units in one. All amenities were great!! Loved it & highly recommended!
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    4 of 5 stars (20) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    5 of 5 stars Reviewed 21 July 2013
    I chose the Pelican Landing due its proximity to Duvall Street and the ability to secure the rental for daily rates. The unit was spacious and had a lot of accommodations within...
    4 of 5 stars Reviewed 21 May 2013
    We stayed in a two bedroom unit, and had other friends in a separate unit. When we first pulled up we were a little worried because the outside is rather plain. We were...
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    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Hot Tub
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    About this property
    Part of Conch Republic Cottages 'Porchside Paradise' is located in the front section of the 'Conch Republic Cottages'. This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
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    1 / 26
    4 of 5 stars (9) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
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    5 of 5 stars Reviewed 14 November 2014
    Loved this place.It's exactly as pictured online. Loved the heated pool and the tropical feel of the pool area.Great location. Our only complaints: pull out couch needs replacing...
    5 of 5 stars Reviewed 20 May 2014
    This property is in a fabulous location right in the heart of old Key West and walking distance to everything, we didn't use the car for the six days we were here. Loved the...
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    1 / 27
    5 of 5 stars (11) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    • ?
    About this property
    SeaShadows is a townhouse located just 2 blocks from Duval Street and a few minutes walk from Mallory Square. Down the street is Ft. Zachary Taylor Park where you can spend the day fishing, swimming, barbecuing, walking, and anything else that you can think of doing in the sun. It sleeps 4... View all property information
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    5 of 5 stars Reviewed 1 July 2013
    The house was very nice and well kept and within walking distance to just about anything. We did a lot of walking and actually ate in most of our meals.
    5 of 5 stars Reviewed 25 May 2013
    An absolutely fantastic holiday home away from home. The cleanliness of the house is an absolute joy, and there is every household amenity to make your stay comfortable. It is...
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    4.5 of 5 stars (20) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder,... View all property information
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    5 of 5 stars Reviewed 11 December 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    5 of 5 stars Reviewed 25 October 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    4 of 5 stars (18) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located inside the Villas known as Old Town Garden Villas Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, cordless telephone, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, a/c... View all property information
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    5 of 5 stars Reviewed 25 June 2014
    I can't say enough about this rental! Excellent location, very clean and the courtyard is amazingly beautiful.. You feel like you are in a private paradise on the island.. The...
    5 of 5 stars Reviewed 14 June 2014
    We stayed here the first week of June 2014. We were welcomed by management at the rental office, offered a cold beverage, and given an umbrella for our use. We were picked up at...
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    From
    €230
    / Night
    View Details
    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    TAKE 25% OFF: -- Stay April 4-6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1,025. -- Stay April 11-14 (3 nights) and pay a reduced rate of $1,125 for all three nights instead of $1,500. -- Note, taxes and fees will be added to all rates. Wake up to the sun rising... View all property information
    Make Enquiry