We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Key West House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $547 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    187 Matching Rentals in Key WestView all 417 rentals
    Sort by:
    Default
    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 15
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    KWO - 2 BR/2 Bath, Private Pool, Separate Cottage1 / 23
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    Great location in Old Town, away from Duval Street, but still within walking distance to great restaurants and Duval if that's your idea of fun. The house has everything you...
    Reviewed 23 April 2017
    We had an amazing time in Key West and we were pleased with the rental. We would go back to Key West Oasis for our next visit.
    See all reviews
    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Casa Havana1 / 24
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
    See all reviews
    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 19 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
    See all reviews
    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (49)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    Casa Del Sol is a wonderful town house - location absolutely central and within bike/walking to Old Town.All amenities are tip top as was the furniture, porch, bikes etc. They...
    Reviewed 30 May 2017
    This home is so clean and so beautifully decorated with art work in every corner! Has everything you need for a great vacation. It will be so sad to leave in two days. A great...
    See all reviews
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Save time - get the best Key West rentals sent straight to your email!
    Get the List
    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 20
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2017
    We have stayed here 2 or 3 times. It is small, but there are just 2 of us and our dog. Works for us! Very cute and cozy. Washer & dryer. Compound is quiet and...
    Reviewed 13 August 2016
    The Cigar House has one the best location you can expect in Key West, close to Fort Zachary, Hemingway's House or Duval St. and all its attractions.This lovely house is full of...
    See all reviews
    About this property
    OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    The Dolphin House1 / 23
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
    See all reviews
    About this property
    THE DOLPHIN HOUSE: Twice the comfort and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between....
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Eyebrow Suite-1 BR/1BA steps off Duval St.1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 23 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
    See all reviews
    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Alluring Porches1 / 24
    (16)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2015
    Everything as advertised and more. Immaculate, tastefully decorated, roomy. Close to Duval. Porches on each bedroom and off living room. Huge master bedroom with large porch...
    Reviewed 9 August 2015
    I was a little apprehensive about booking this place because it didn't have many recent reviews, but I am very glad we booked. The price was very reasonable for Truman Annex...
    See all reviews
    About this property
    ALLURING PORCHES - A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround this home and a beautiful open air feel brings the outside in while you just...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Bloom'n Paradise1 / 24
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
    See all reviews
    About this property
    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Amelia Home1 / 24
    (54)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2015
    What a great place to stay. Location is perfect. Everything you need is supplied. Decor and Landscaping were also wonderful. Already talking about next years stay. Nothing...
    Reviewed 2 April 2014
    Amelia Home was a great place to stay and experience Key West. The house is very clean and in excellent condition. The pool made the stay.The location is great. You can walk to...
    See all reviews
    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Amelia Home. This is the Key West Florida vacation home rental you have been seeking, tucked away in one of the...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Coral Casita1 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    We stayed at Coral Casita for two weeks with our extended family. We were very happy with the rental accommodation from start to finish. The property was very clean and well...
    See all reviews
    About this property
    Coral Casita - Weekly Vacation Rental Completely re-designed, re-decorated and ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A spacious 3 bedroom townhome...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    The Water's Edge1 / 25
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2017
    The house was gorgeous, and the sunset view from the balcony lived up to expectations... Short walk to Duval Street... Totally recommended
    See all reviews
    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Newly remodeled family home with a shared swimming pool and fitness center!1 / 32
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Terrace
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Washer
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca Too is the perfect get-a-way vacation rental for two! Casablanca Too is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Ecco Domani1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ECCO DOMANI – Ecco Domani means 'Here Tomorrow' which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off street parking and attractive appointments -- a wonderful Key West escape that you will want to come home to year after year. Enter...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Breezy Bungalow1 / 24
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Great location - within walking distance of Duval Street, Mallory Square, Hemmingway House, and many other attractions that we visited. The Truman complex, where it is located...
    See all reviews
    About this property
    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    HISTORIC KEY WEST  - Main House - Sleeps 101 / 23
    (4)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
    Reviewed 29 November 2011
    I rented The Main House at Bahama Gardens for a family vacation of about 10 days over Thanksgiving. There were 5 of us, myself, my husband, two adult sons and one son's...
    See all reviews
    About this property
    OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of ten (10) guests - (1) queen bed, (1) full bed, (1)...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    The Hemingway1 / 25
    (26)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2015
    The property is located in a great convenient area. It is in close proximity to the beach , restaurants , shopping and entertainment.We enjoyed utilizing the rear deck each...
    Reviewed 7 December 2014
    We really enjoyed the condo. It was clean and well kept. It was close to everything in Key West. We had a great time. I would recommend this to anyone. I felt right at home...
    See all reviews
    About this property
    THE HEMINGWAY -- A beautiful 2 bedroom 2 bath Florida Keys rental home located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to restaurants, nightlife, entertainment,...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'. This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Leeward Isle Key West Retreat1 / 24
    (35)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2014
    We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.
    Reviewed 20 November 2013
    We just love this little get away home that we get to stay at when in Key West. The new owners have done a nice job of re-modeling and the Leeward Isle is so comfortable.
    See all reviews
    About this property
    LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot for this Key West vacation condo you know you are someplace special. A small gated and secured compound with only 13 properties, this townhome community is quiet and private while still...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most prestigious gated community in the heart of historic Old Town. 2 bedrooms, 2.5 baths; each queen-bed room has...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Petite Maison - Key West Cottage: Sleeps 4 Steps from Everything! Parking Too1 / 19
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Parking
    • Terrace
    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Right off the main street but behind a sister building giving you quiet. The cottage is small, especially the bedrooms and bathrooms. One bedroom didn't have a dresser. But the...
    See all reviews
    About this property
    Petite Maison is a designer Key West Guest Cottage that is located in the Gallery District of Duval Street. It is located on a quiet hidden lane behind Duval Street. Petit Maison is just a few blocks away from the Southernmost Beach, night clubs, and tourist areas which make it a perfect spot to...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2017
    Spacious property with two pools, friendly neighbors and charming location just a short walk to all of old town Key West.
    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...
    See all reviews
    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated historic 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. The house can be described...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Coral Garden1 / 23
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2013
    Our visit to Key West was amazing. At Home in Key West Inc. has the best services they were very informal and personal. At Home made sure we had everything that was needed for...
    Reviewed 16 August 2013
    We were thrilled to see that the home was so well kept and looked exactly like the photographs. I would definitely recommend people staying here especially if you have children...
    See all reviews
    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Tropical Dreaming1 / 24
    (58)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2017
    Nice and quiet with pool. Two bed rooms and two baths. Nice and clean house only draw back, has limited parking since we had 2 cars.
    Reviewed 22 July 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
    See all reviews
    About this property
    TROPICAL DREAMING -- A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of both worlds while vacationing in Old Town. Only a short stroll over to Duval Street, where entertainment and activity abounds or 4 blocks to the Atlantic...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Artist Garden1 / 24
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 October 2015
    We stayed at the Artist Garden for our triple birthday celebration (3 friends within a week). The house is beautiful. It is located within Truman Annex. And you can seriously...
    Reviewed 11 April 2014
    We enjoyed a 2 week stay in this beautiful house. The location is perfect. We were only a 5 minute walk to Mallory Square and a 10-15 min walk to other favorite restaurants. We...
    See all reviews
    About this property
    ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Patio
    • Central Heating
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MONTHLY RENTAL ONLY This spacious 3 bedroom, 2 bath has all new stainless steel appliances and cabinets in kitchen, 15 ft. bar with wine cooler, new 55' flat screen in living room with cable TV. Large master bedroom with king size bed and French doors opening to pool deck plus 55' flat screen...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Crowner's Jewel1 / 24
    (35)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2017
    Stayed recently for a week and while the condo was clean and well maintained , and the location was great the showers were just way too small. There are two bathrooms upstairs...
    Reviewed 6 November 2014
    Great Place! 2 blocks from Duval. Spacious, great amenities. Showers are tiny but at least there are 2 which helps bigger groups get ready. Clean. Nice neighborhood.
    See all reviews
    About this property
    CROWNER'S JEWEL: Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart of the exclusive gated community of Truman Annex. New owner has added lots of upgrades to make you feel welcome in his new home...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Central Heating
    • Washer
    • Balcony
    • Patio
    • Waterfront
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town. The Truman Annex offers...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Make Enquiry
    Duval Penthouse1 / 24
    (24)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    Love the Duval Penthouse; our second year staying there. Fantastic location, clean, well taken care of. Only one thing I would change... the mattress in the Master bedroom is...
    Reviewed 27 March 2014
    The place was awesome. As everyone says, the back bedroom is a bit noisy being right on Duval and next to Willie T's but still a great place. I found that leaving doors open...
    See all reviews
    About this property
    DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist,...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Conch Wind1 / 23
    (36)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Terrace
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2016
    This place is very nice and has all the convenience's of home. Located one block off of Duval street so you can walk Duval, drink and not have to drive home. The weather was...
    Reviewed 15 May 2015
    Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.
    See all reviews
    About this property
    CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound. Plenty of space, beautifully furnished with all attention given to your comfort and...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Potter`s Cottage: Sleeps 5, Walk to the Beach & Nightlife, Private Dip Pool!1 / 29
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    The pictures are entirely accurate, this place is adorable and perfect for two couples. The two bathrooms was a deal sealer for us. It's near the main drag and we love, love...
    Reviewed 18 September 2016
    We stayed at the Potter's Cottage and thoroughly enjoyed our experience. The property was in fantastic condition - fully modern with generally high quality finishes. One full...
    See all reviews
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Bahama House1 / 24
    (26)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2017
    Bahama House was a wonderful choice for a family gathering and week-long vacation in Key West. Its location in a quiet, short street, a block back from Duval Street, provided us...
    Reviewed 13 April 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
    See all reviews
    About this property
    BAHAMA HOUSE - Location, Location, Location! Totally gorgeous, this spacious house rental Key West is conveniently located on a quiet street in the heart of Old Town Key West around the corner from the fabulous shops, activities, restaurants and nightlife on Duval Street. Luxuriously appointed...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Beautiful property. This house was stunning, thank you so much for letting us stay there. All amenities were provided. I love all the plants and trees surrounding the pool and...
    See all reviews
    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included.
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Royal Palm1 / 25
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2016
    Highly recommend this rental property. Located in a lovely quiet area but 5 minute walk to Duval Street. Fully equipped property could not have asked for anything more. Lovely...
    See all reviews
    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Down Island Digs ~ Weekly Rental1 / 14
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2017
    We stayed for a week at 508 Bahama St. We were 1 block behind Duval but you would never have known it. The backyard is so peaceful and where we basically lived all week...
    Reviewed 13 June 2016
    If you want to be near the heart of Duval, but never hear it when you choose to take a break, then this is your place. The backyard garden is amazing with gorgeous landscaping...
    See all reviews
    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Havana Moon ~ Weekly Rental1 / 11
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2016
    The staff, the home were great our second time in Havana Moon, we stay there again, and cannot beat the privacy
    Reviewed 17 March 2015
    We had a great time staying here because we could walk/bike to everything! There is a bike/electric car rental place across the street and they are so nice! (Tropical Rentals...
    See all reviews
    About this property
    Open the front door of the hand crafted Havana Moon Key West cottage located on Upper Duval Street, step from the porch, and look south toward Havana Cuba and... Mmmm... You'll catch a view of the ocean where the full moon rises with a soft salt southern breeze. Originally built in the late 1800's...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Island Wind1 / 23
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2016
    Spent a a week here. We loved everything about it. Great neighbors and relaxed atmosphere. House was absolutely perfect. Everything you need is there, just bring a bathing suit...
    Reviewed 6 December 2013
    Enjoyed Thanksgiving week here. Island Wind is in a perfect location. It is an easy walk to the southern most beach & a doable walk to Mallory Square. Duval is only a...
    See all reviews
    About this property
    ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award winning Windward Park, a gated and secure compound consisting of...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Casablanca: Perfect Getaway for 2, Soak up the Sun! Private Pool & Parking1 / 34
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    Nice to have a separate living room with a desk for relaxing in the evenings. Wi-Fi was fine - didn't watch TV. Spent a good part of every day outside, by the lovely private...
    See all reviews
    About this property
    Casablanca is the perfect get-a-way vacation rental for two! Key West Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a spacious vacation rental with the added bonus of off street parking and a private heated...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Previous
    List your property
    Owner log in