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Apartments in Key West, FL

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    Travellers to Key West are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 5
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 16
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 30 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 11
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • Internet Access
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    • Outdoor Dining Area
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 29 July 2015
    Everything you need, easy to get around island. Quiet, no view of water. Great place for the price. I would stay here again.
    4 of 5 stars Reviewed 26 March 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $335
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    • Secure Parking
    • Washer
    • Internet Access
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    • Satellite TV
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 stars Reviewed 26 October 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    1 / 13
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $384
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    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Porch
    • Washer
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
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    • x
    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 22 October 2015
    Being a Florida local, I travel to Key West quite often for the past 13 years and have never had a better and more pleasant stay than at the Duval Balcony. The owner was waiting...
    5 of 5 stars Reviewed 22 October 2015
    We stayed here in July and it was just what we were looking for. Pretty roomy for Key West, very clean and well kept, and right on Duval St. When we wanted to go out to eat, drink...
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    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    $3,493
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    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 week ago
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service to...
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    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    $152
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    • Patio
    • Internet Access
    • Grill
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
    • Smoking allowed
    • Elder access
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    About this property
    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $419
    / Night
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    • Grill
    • Satellite TV
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 September 2013
    We have been renting a condo at this property for many years under different mangement companies and the folks managing it now are top notch the are doing a great job
    4 of 5 stars Reviewed 31 July 2013
    The location was perfect for us since we had a boat and the rental came with a boat slip. Our balcony even looked down on our boat. Room space was very adequate for the eight of...
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    1 / 26
    5 of 5 stars (27) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $2,515
    / Week
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Satellite TV
    • Patio
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 December 2015
    We loved our stay at Casa del Sol. The location was perfect for sight seeing and walking everywhere. We never used our car for the week's stay. The beds were comfortable, the...
    5 of 5 stars Reviewed 31 August 2015
    Casa del Sol is in a perfect location in Key West with an easy 2 block walk to Duvall Street but in a quiet relaxing residential area. The condo is very clean, well equipped and...
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    1 / 23
    4.5 of 5 stars (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $419
    / Night
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 13 July 2015
    The actual unit was really nice and accommodating for us (a party of six). However, from the time of check in and a few times afterwards, the management official working at the...
    4 of 5 stars Reviewed 25 January 2014
    Nice location looking out on Garrison Bight Marina and close enough to Old Town. Super spacious unit was very nice and clean. Completely equipped and has washer/dryer stack. A...
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    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $270
    / Night
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Balcony
    • Porch
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living for yourself. From its fabulous... View all property information
    Location Information
    Key West, Florida Keys
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $210
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    • Outdoor Dining Area
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4 of 5 stars (37) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $360
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    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 16 December 2015
    We stayed in this property for two days. We had a good time. Staff is friendly. They have everything what we need there. I read reviews about this property and some one mentioned...
    4 of 5 stars Reviewed 12 December 2015
    Nice location. Hot tub, patio nice, porch fun to watch traffic a passerbys with morning coffee. Houe is cute but needs a little TLC. Fingerprints on walls and doors, missing...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Balcony
    • Terrace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $559
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    • Air Conditioning
    • Sauna
    • Satellite TV
    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool...
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Two Bedroom Premiere Ocean View This is a beautiful top floor two bedroom ocean-view unit at 1800 Atlantic. You cannot get a better view than this. King bed in the master and a queen in the 2nd bedroom. High speed wireless internet access. There is a full size fully equipped eat in Kitchen. Full... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 weeks ago
    We went on a family vacation in may 2013 to the Keys and decided to say in the condo because of the great location to the beach. The condo was very clean and had everything we...
    4 of 5 stars Reviewed 18 September 2010
    December 2009 was our fifth time staying at the 1800 atlantic condo. My husband and I are anticipating our stay this year as it is the best value for our dollar. Julia at all...
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    1 / 24
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $356
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    • Balcony
    • Terrace
    • Internet Access
    • Washer
    • Parking
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 28 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 that...
    5 of 5 stars Reviewed 17 January 2013
    We chose Banana Key just a few days before we actually got there due to a last minute vacation opportunity. I worked with Tim at Historic Hideways and couldn't have been happier...
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $992
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    • Internet Access
    • Satellite TV
    • Sauna
    • Waterfront
    • Hot Tub
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Construido en la década de 1950, el complejo rezuma encanto de la época, sin retraso en el crecimiento de las comodidades. Las habitaciones cuentan con obras de arte cubano, TV de pantalla plana, mini-nevera, y hamacas. El hotel presta huéspedes coloridos sarongs para relajarse, y algunas... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $454
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    • Satellite TV
    • DVD Player
    • Terrace
    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool...
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Additional amenities include: sofabed, coffee maker, nearby beach, nearby bank, nearby internet cafe, ice maker, near beach, nearby medical... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 16 July 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for the...
    5 of 5 stars Reviewed 14 June 2014
    This vacation rental was huge, nicely decorated, and a great place to stay. The pool, jacuzi, pool house, and courtyard were all amazing - so nice, we spent one full day just...
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    1 / 30
    5 of 5 stars (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $1,361
    / Night
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    • Balcony
    • Air Conditioning
    • Patio
    • Private Outdoor...
    • Internet Access
    • Washer
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 July 2015
    The home was just lovely. Very clean, nicely furnished and quite comfortable. The pool was so refreshing and the courtyard was tropical with beautiful outdoor furniture. The...
    5 of 5 stars Reviewed 5 July 2015
    This house is in the perfect location with all of the need amenities! Just a wonderful place to stay and a great time! Enjoy ....you won't regret it!
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $349
    / Night
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (58) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $349
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    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 3 weeks ago
    We enjoyed our stay and made use of the bikes and the pool. It is about a 10 minute drive to downtown and walking distance to a couple restaurants. We had a family of five and...
    5 of 5 stars Reviewed 4 July 2015
    Judy's condo, Tee by the Sea is really a great place to stay. The location is away from the crowds but close enough to be only a short drive or bike ride away. The condo has...
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    $432
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    • Internet Access
    • Terrace
    • Outdoor Dining Area
    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    5 of 5 stars (53) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $293
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    • Air Conditioning
    • Parking
    • Hot Tub
    • Balcony
    • Wi-Fi
    • Satellite TV
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
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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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    Pamela's condo in Key West, FL was clean, nicely decorated and had an "at home feel". The balcony view of the pool is very beautiful and relaxing. This was our first family...
    5 of 5 stars Reviewed 29 December 2015
    Stayed with my wife and two teenage kids. The condo was very clean and well stock with every day essentials. The owner Pam is super to deal with and I would go back anytime...
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    1 / 26
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ************************************************************************************************************************ ************************************************************************************************************************ Wake up to the sun rising over the sparkling Atlantic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 28 December 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
    5 of 5 stars Reviewed 5 November 2015
    We had such an amazing time in the Florida Keys. Staying at Atlantic Sunrise was icing on the cake. The condo is beautiful and the owners were so very kind! The notebook with...
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    1 / 32
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    • x
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    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 5 days ago
    The boat is big and very comfortable for my family (5) very luxurious to the smallest details, has a jacuzzi on the top and kajacs to navigate the beautiful sea. It was awesome...
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    1 / 31
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    $25,146
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    About this property
    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly... View all property information
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    Key West, Florida Keys
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    $2,550
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    About this property
    New owners invite you to enjoy this vacation rental aptly named 'Seas the Day!' This newly updated 2 bedroom 1 bath first floor condo is located in the Shipyard section of the Truman Annex. If you are looking for a great location central to all that Key West has to offer, look no further! Park... View all property information
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    Key West, Florida Keys 33040
    1 / 49
    2 of 5 stars (1) Poor
    11 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    $3,423
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    • Terrace
    • Porch
    • Balcony
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    • Pet-friendly
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    • x
    • ?
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    About this property
    The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $342
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    • ?
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 28 May 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed 30 March 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 15 October 2015
    Location, while good very close to Airport which was noisy at times. Bedrooms good size. However, plastic mattress protectors were uncomfortably hot, unnecessary and had to be...
    5 of 5 stars Reviewed 26 June 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $8,382
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    • ?
    • x
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    • Elder access
    • x
    • x
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $196
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    • x
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    • x
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    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 3 May 2014
    The condo was exactly what I was looking for and it was represented accurately. It was about fifteen minutes from Duval street, had a water view, it was quiet and the interior...
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    1 / 18
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    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 non-boat speakers) has all cooking, baking and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 weeks ago
    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 nice...
    5 of 5 stars 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 and...
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    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $1,781
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    • ?
    About this property
    La Casita en Cima is now available for monthly rentals! The 'Little House on the Summit' rests on the highest point of the Island of Key West. Located on Angela Street in the heart of Historic Old Town. This historic home built in the 1930's, has just completed a full renovation with loving... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $7,684
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    • Pet-friendly
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    • ?
    • x
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    • x
    • x
    About this property
    3 bedrooms, 2 full bathrooms, sleeps 6 Boat in, boat out. Inspired by Balinese design this private waterfront retreat has deep-water access and is the ultimate base for the ocean enthusiast. Choose to escape, relax and meditate by the waterfall or head out for a day of adventure on the high seas.... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $2,096
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    • x
    • 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
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    5 of 5 stars (58) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $286
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 weeks ago
    Very clean unit, everything up-to-date. Affordable rental. Located on North East side of the Island, away from heavy traffic but close to the bike path that circles the island...
    5 of 5 stars Reviewed 4 weeks ago
    Stayed for 3 days and had an excellent stay. Great place if you are travelling with kids. The swimming pool is right next to the condo so kids could get their water fun as the...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    $391
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    • x
    • ?
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    • x
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    About this property
    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
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    Key West, Florida Keys
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
    About this property
    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    $377
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    • x
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    • x
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    About this property
    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with... View all property information
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    Key West, Florida Keys
    1 / 17
    5 of 5 stars (22) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $279
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
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    • x
    • x
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    • ?
    • ?
    About this property
    Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'. The original local artwork throughout... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 13 September 2015
    I arrived on a rainy, nasty day in Key West. It was pouring. Duval Street was flooding. The temperature was in the 50s. But I was in Key West, so it couldn't be all bad. It...
    5 of 5 stars Reviewed 11 December 2013
    We have been traveling to Key West 1-2 times a year for about 15 years and have stayed everywhere from the most economical to the high end resorts and will confidently say this...
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    1 / 26
    5 of 5 stars (33) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $475
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    • Internet Access
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    • Sauna
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 22 December 2015
    The owner of this condo. goes out of her way to make your vacation enjoyable. She has beach chairs, beCh towels, sun screen, beach umbrellas, etc etc. available for you to use...
    5 of 5 stars Reviewed 4 December 2015
    The condo was very nice and included all of the items we needed. It is close to the beaches and only a few miles from dowtown. My grandkids loved the pool, tennis and ping pong.
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    1 / 12
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • ?
    • ?
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 11 February 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed 1 November 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $5,309
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    • Pet-friendly
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    • x
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    • x
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
    • x
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    • x
    • x
    About this property
    Share 5 Star $2.4m Beautiful New Large modern Home on very quiet street in Old Town of Key West. Advantage is Location, Location and Location! Own fully furnished bedrooms with Queen size bed for 1 - 2 (see photos) with 32' flat screen TV and 2 french doors leading onto private balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 19 April 2015
    Lovely air conditioned home well located for all of Key West amenities. Quiet and well designed and furnished. Great host, very accommodating. We had a ball. Liz & Graham
    5 of 5 stars Reviewed 2 April 2015
    We were out a lot, biking, visiting and eating. However, each time we came back to Don's place it felt welcoming and friendly. Don is a delightful host. The bedroom with...
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    Holiday Rental Accommodation on Key West

    The diversity of the holiday rental accommodation available on Key West means that there is something available to suit every budget and surely all tastes. From cottages and modest condos, to villas and townhouses, to penthouses and country estates, Key West has it all, meaning that your holiday in Key West can be as free of restriction as possible, at a price you can afford. If you want the freedom to explore Key West at a time and in a manner of your choosing, selecting the holiday rental best suited to your individual requirements is the way to achieve your goal.

    Water sports in Key West

    The weather and geography of Key West make it an ideal location for a great many different types of water sports. Fishermen of all disciplines can choose from the art of fly fishing for tarpon, to deep sea fishing expeditions from a boat and most options in between. Those simply interested in being out on the water can go pleasure cruising on a charter boat, perhaps to view the dolphins and other marine life, hire a kayak and meander through the waterways at their own pace, or even jump on a jet ski and enjoy some high speed thrills. Scuba divers can admire the natural coral reefs or explore the wrecks in the area, some of which were deliberately sunk to form artificial reefs.

    Popular attractions in Key West

    The beaches of Key West are both numerous and beautiful but a visit to the Fort Zachary Taylor State Park allows you to combine your beach relaxation and activities with an inexpensive tour of the fort, or perhaps a casual stroll along one of the nature trails. Art lovers will find a great many galleries of interest in Key West, with the majority local to the popular Duval Street part of town. Key West Golf Club is not only about allowing golf lovers to practise their swing, it also has a popular restaurant and bar, which could perhaps serve as a point at which non-golfers can arrange to meet players after their round. One monument not to miss in Key West is the small round landmark which denotes the most southerly part of the continental United States.

    Restaurants and bars in Key West

    Duval Street is the popular centre of Key West in so many ways, not least when it comes to restaurants. When you are eating out from your Key West holiday rental of an evening, you may wish to sample popular outlets such as Nine One Five or Mangoes, or try the Banana Café for breakfast or lunch. Blue Heaven in the Bahama Village is the place to sample outdoor dining of the highest quality, with an indoor option available if preferred. The bars and clubs of Key West are plentiful in the extreme, with options to suit all tastes and requirements and allow you to party the night away in style.