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.

Vacation Rentals in Key West, FL

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
    $406 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Applied filters: Clear All
    1 / 25
    4.5 of 5 bubbles (13) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 29
    4.5 of 5 bubbles (28) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 28
    4.5 of 5 bubbles (23) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 29
    4 of 5 bubbles (24) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Balcony
    • Shared Outdoor Pool...
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit opens to the living room,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 13 March 2015
    We have stayed in quite a few places in Key West, and the location was good, but there are things to be aware of. One thing to know is that it is a vacation rental unit in a...
    3 of 5 bubbles Reviewed 19 January 2015
    Overall was okay. Some details that were lacking made the stay not quite as good as expected for the cost. TV was small. Guest BR bed was not comfortable. There was mold on...
    See all reviews
    1 / 25
    4.5 of 5 bubbles (21) Very good
    Studio, 3 Bathrooms, Sleeps 7 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private,... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 29 October 2015
    The location is perfect, almost in the middle of it all. Downstairs are nice restaurants. If you don’t want to cook, go to NY Pasta Garden down stairs. They serve a fantastic...
    5 of 5 bubbles Reviewed 13 September 2015
    The check in process for KWVR was fast and easy. The office staff is very friendly and helpful. We found Casa Bonita spacious for the four of us and our dog. The kitchen is well...
    See all reviews
    1 / 27
    4.5 of 5 bubbles (15) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 10 December 2014
    Amazing condo ! Great Staff ! Beautiful place with comfy beds and all the comforts of home and then some ! Hot Tub !!! Full kitchen w/washer and dryer. Gated parking and 2 pools...
    5 of 5 bubbles Reviewed 21 August 2014
    I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
    See all reviews
    1 / 32
    4.5 of 5 bubbles (36) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 March 2016
    My husband and I stayed at this condo for 2 nights with another couple. The location was great. Although we were near the main street, this unit (R9) was quiet (except for the...
    4 of 5 bubbles Reviewed 19 January 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
    See all reviews
    1 / 16
    4.5 of 5 bubbles (47) Very good
    Studio, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Terrace
    • Private Outdoor...
    • Balcony
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the action at Duval Square just south of Truman. The residential units sit in a courtyard setting above a retail/office courtyard below with the shared pool... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 22 October 2014
    6 of us stayed in this condo the last week of September, it was fantastic. Our nephew got there a few hours before us but we had called ahead and told them about it so they had no...
    5 of 5 bubbles Reviewed 3 April 2013
    Our group of 8 stayed at Duval Square Penthouse for 6 nights in March and we had a great time. The location of the condo is awesome, as we were able to walk to everything. The...
    See all reviews
    1 / 15
    4 of 5 bubbles (22) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Terrace
    • Private Outdoor...
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch, two bedrooms and two baths. There is a shared... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 18 August 2014
    All the reviews were spot on. Best accomodation we've stayed at by far which made our holiday that much more enjoyable. Location is perfect - far enough down Duval to be away...
    5 of 5 bubbles Reviewed 20 January 2014
    We did stay at this place but through a private owner. We did have contact with Rick from Rent Key West Vacations. He went out of his way for us. He helped out some friends and...
    See all reviews
    1 / 18
    4.5 of 5 bubbles (15) Very good
    Studio, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Parking
    • Terrace
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers a well- equipped kitchen, a living room that opens to a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 11 April 2013
    Total great experience at Duval Square Retreat. From the initial contact, through help with some transportation, to the warm welcome and tips on local must-sees, this is a fine...
    5 of 5 bubbles Reviewed 28 March 2013
    The location of Duval Square is right on. Convenient, safe, comfortable. The decor was not to my liking, but that is a matter or individual taste. It wasn't horrible. It was...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 15
    4.5 of 5 bubbles (40) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool...
    • Air Conditioning
    • Patio
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 4 August 2016
    My family and I stayed for 6 days and had a great time. As it was very hot in Florida this time of year the location was great to stop for a quick snack and break. Centrally...
    5 of 5 bubbles Reviewed 27 April 2016
    We had a great time, the house was nice, but the dishwasher was broken on the bottom rack, the electrical outlet upstairs blew and they had to come fix it, the faucet in the...
    See all reviews
    1 / 23
    4 of 5 bubbles (26) Very good
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Private Outdoor...
    • Balcony
    • DVD Player
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone WALK-UP buildings in the Duval Square complex. You enter a large open living, dining,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 20 December 2012
    Very clean and great location right off Duval Street. Excellent Restaurants in the courtyard. "At Home in Key West" rental department was very helpful in secruing the perfect...
    4 of 5 bubbles Reviewed 12 September 2012
    The 3 bedroom condo I stayed in is nicely furnished and quiet, except for the roosters in the early morning! But even the roosters added to the charm of Duval Square. The 2...
    See all reviews
    Also consider these instantly bookable condos
    4.5 of 5 bubbles (215) Very good
    Rose Lane Villas
    Apartment / Speciality Lodging
    Show Prices
    4 of 5 bubbles (421) Very good
    Sunrise Suites Resort
    Apartment / Speciality Lodging
    Show Prices
    4 of 5 bubbles (138) Very good
    1800 Atlantic Suites
    Apartment / Speciality Lodging
    Show Prices
    4 of 5 bubbles (48) Very good
    Coral Hammock Key West by KeysCaribbean
    Apartment / Speciality Lodging
    Show Prices
    4 of 5 bubbles (11) Very good
    Key West Harbour Guest Suites
    Apartment / Speciality Lodging
    Show Prices