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 Cottages

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €196 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    Applied filters: Clear All
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 99
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 20
    4.5 of 5 stars (50) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    1 / 22
    4 of 5 stars (45) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in the heart of Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room but appreciate the amenities of a vacation rental. Sunny and bright this cottage has... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 24 July 2016
    We stayed at the osprey in bungalow #8. This place was clean with a very comfortable bed, sitting area, kitchenette with a full size refrigerator and a nice deck for morning...
    5 of 5 stars Reviewed 21 March 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
    See all reviews
    1 / 24
    4.5 of 5 stars (27) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Terrace
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor...
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 28 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
    5 of 5 stars Reviewed 6 April 2015
    Great unit, very well maintained. Repeat customer and would recommend this to anyone! I would only add chairs to the front porch.
    See all reviews
    1 / 16
    4.5 of 5 stars (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool...
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This charming one bedroom cottage is the perfect hideaway. 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. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 19 September 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
    5 of 5 stars Reviewed 11 May 2013
    My new husband and I selected ann Street Tranquility for our honeymoon and we could not have been more happy with our choice!Everything about ann Street Tranquility was amazing...
    See all reviews
    1 / 15
    4.5 of 5 stars (47) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Satellite TV
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming 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
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 2 July 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    5 of 5 stars Reviewed 1 August 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
    See all reviews
    1 / 14
    4.5 of 5 stars (46) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. 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. Within 2 blocks you'll find Key West... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 3 July 2016
    Very quaint home with just enough space for two. Decor makes you feel like you are in Bali and it has everything you need including pool towels. The property is very secluded...
    5 of 5 stars Reviewed 27 June 2015
    We were fortunate enough to spend a week in this little gem of a studio! From the moment we picked up our keys at Rent KW, we were impressed. The staff were not only super...
    See all reviews
    1 / 41
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 23 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    5 of 5 stars Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised however...
    See all reviews
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Private Outdoor...
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This newly renovated unit is located just two blocks from world famous Duval Street surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway. The bungalow features an one level open space living/dining area, full kitchen and a spacious... View all property information
    Location Information
    Key West, Florida Keys
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 26
    5 of 5 stars (21) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Shared Garden
    • Hot Tub
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 17 December 2015
    My husband and I stayed with Kayla and Steve for five days and it was the most relaxing fun filled stay ever. The accommodations were very clean and our hosts were the...
    5 of 5 stars Reviewed 12 February 2015
    Atlantis House is a very special hideaway. It is called a guest house, and we were truly the guests of Steve and Kayla. They were so welcoming from the day we arrived: helping...
    See all reviews
    1 / 25
    4.5 of 5 stars (52) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Grill
    • Shared Outdoor Pool...
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 15 August 2016
    I honestly hesitated to write this review because I want to keep it all to myself. My husband and I are unwilling transplants, having lived in Key West until about 6 years...
    5 of 5 stars Reviewed 26 July 2016
    Key West was a bucket list trip for my husband & I. It was perfect!! Tim with Historic Hideaways was wonderful in making this an unforgettable trip. We've decided we will be back...
    See all reviews
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    1 of 5 stars (1) Terrible
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
    Location Information
    Key West, Florida Keys