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.

Holiday Rentals near Duval Street

Duval Street, Key West, Florida 33040
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
    €231 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    Travellers to Key West are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    1/2 Block to Duval, World of its own -Nassau Suite1 / 34
    (20)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (39)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Center of It All - Paradise Island Suite1 / 14
    (30)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Duval Balcony - Suite Mischief1 / 13
    (10)Excellent
    0.1 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Balcony
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    Great place to stay. In the middle of things to do. Place was clean and Tom kept checking to make sure that everything was satisfactory. WILL definitely stay there again.
    Reviewed 16 July 2017
    This place was great. Clean and well equipped. You can watch the performers across the street from the balcony. The host was personable and informative.
    See all reviews
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (46)Very good
    0.3 kilometres from Duval Street
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Was very Happy with service and location. Would love to come back. Staff was very friendly and accommodating. Paradise island suite was neat and clean and we all had a Wonderful...
    Reviewed 2 weeks ago
    Key West Bahama House is great even if weather not so good. Pool is warm and Owner is very nice. Would visit again.
    See all reviews
    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    LOCATION! Mango Hideaway-King Suite w/ Jacuzzi steps off Duval St.1 / 18
    (5)Excellent
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Grill
    • Private Garden
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2017
    My husband and I stayed here for our wedding anniversary. Very cute and private little place. Perfect for couples. We would definitely come back again and recommend it to others...
    Reviewed 6 May 2017
    The Mango Hideaway is a nice spot in the middle of Old Town. Walking distance to everything. Private patio and entry off of the side street are a plus. Great location and a...
    See all reviews
    About this property
    Mango Hideaway 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 as...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Truman Annex Irish Condo Innisfree1 / 33
    (5)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 24 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
    See all reviews
    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May1 / 17
    (1)Excellent
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Secure Parking
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location!! Sunrise off Southard has it all! An upscale one bedroom home offers tropical beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 22
    (13)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have 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 18 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Truman Annex Shipyaard with Tropical Garden1 / 8
    (2)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Private Garden
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    We love staying here. There was plenty of room and the condo was nicely decorated. We walked and biked all over with ease -- great location.
    Reviewed 15 May 2017
    Love love loved the town house. Beautiful. Love cation was perfect. Was able to walk most everywhere. Felt safe walking late at night also. Beautiful location. Can't wait to...
    See all reviews
    About this property
    Decorated in shade of sea foam and coral, this property is located in the Truman Annex and puts all of Key West's top attraction within easy walking distance. French doors open to a garden with hibiscus and cat palms framing a comfortable patio. Both bedrooms have queen beds, with a sofa bed in...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 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  - Conch House - Sleeps 51 / 15
    (4)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2014
    My husband & I found the Conch House online. The property manager, Craig, met us upon our arrival and was very friendly. Throughout our trip, he was very helpful and very...
    Reviewed 22 June 2014
    This property is so beautiful and peaceful.!! Perfect location, 2 short blocks from Duval, 1 block from Ft. Zach beaches. We stayed in the Conch House , We could not have been...
    See all reviews
    About this property
    OVERVIEW The Conch 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 five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Terrace
    • Washer
    • Central Heating
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condominiums. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Duval Balcony - Street Suite1 / 15
    (2)Very good
    0.2 kilometres from Duval Street
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    Tom was very nice and accommodating. He greeted us when we arrived. Great location in the heart of all the action of Duvall st and with this comes noise bring ear plugs for the...
    Reviewed 22 February 2017
    Right in the heart of Duval Street! Great places to eat and party and experience the night life of Key West,
    See all reviews
    About this property
    Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Conch in Training1 / 20
    (6)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Secure Parking
    • Air Conditioning
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    Walking distance to practically everything. Mallory Square, Fort Zachary Taylor, beach, Duval st., grocery store, Hemingway house, and Southernmost point. I stayed for a week...
    Reviewed 14 June 2017
    Great location in the heart of Truman Annex. Re-modeled condo w/updated appliances. Minutes from Fort Zach Beach and Southernmost Beach. Green Parrot, Blue Heaven and...
    See all reviews
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Poinciana House1 / 25
    (47)Excellent
    0.2 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    The house was a 1/2 block off Duvall Street. Was close to all restaurants and attractions. The house was very cute and clean. The pool was fantastic. We would definitely stay...
    Reviewed 5 April 2017
    The Poinciana House is a wonderful small house with pool for two people. My wife and I stayed for a week and had a great experience. The house is perfectly located for...
    See all reviews
    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Make Enquiry
    LOCATION! Eyebrow Suite-Spacious 1 BR/1BA suite w/ Jacuzzi steps off Duval St.1 / 24
    (4)Excellent
    0.2 kilometres from Duval Street
    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 22 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.2 kilometres from Duval Street
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Jan 20-27, Feb 3-10 OPEN: Beautiful, Large condo 2BR/King Beds, Truman Anx, Pool1 / 15
    (5)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Porch
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2017
    We spent two weeks at the shabby chicken. The condo was very comfortable, well-stocked, two large bedrooms. The patio was a wonderful retreat for conversation, relaxation...
    See all reviews
    About this property
    Jan 20-27 & Feb 3-10 is now AVAILABLE! We just reopened a few weeks on the calendar - so definitely book with us and come for a week in our warm winter climate! The completely renovated Shabby Chicken - come stay with the large and proud newest bird in town!! 5-STAR rating and the best floor plan...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Linger Longer1 / 24
    (22)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived...
    See all reviews
    About this property
    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Quilted Giraffe1 / 25
    (3)Excellent
    0.2 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Charming historic home, comfy beach cottage feel. GREAT LOCATION, beautiful pool area great for dining under the stars or a relaxing day in the sun. If your lucky you might get...
    Reviewed 7 June 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is...
    See all reviews
    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    ~ POINCIANA TREETOP ~ Swanky Suite w/ Pvt Hot Tub & Parking - Great Location!1 / 30
    (2)Excellent
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Parking
    • Washer
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 December 2016
    What a great little place to stay. It's so close to town but yet tucked away on a quiet block. The one thing we wished it had was a pool, but the hot tub did the trick. The...
    Reviewed 26 March 2016
    This was an exceptional getaway spot for us as a couple on our first visit to Key West. It's perfectly situated on a quiet lane but close to all the great Old Town attractions...
    See all reviews
    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The second floor unit 'Treetop' sleeps up to 2...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    HISTORIC KEY WEST  - Main House - Sleeps 101 / 23
    (4)Average
    0.3 kilometres from Duval Street
    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 28 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    The Courtyard1 / 25
    (20)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    100% our best rental place in Key West so far and we've been going for over 15yrs!Great location, nice pool, awesome to have a parking spot, secluded behind a gate. The cottage...
    Reviewed 15 March 2017
    The Courtyard is on Fleming, the ideal street to be on when staying in Key West. It's quiet(unlike Duval) and within easy walking or biking distance of any place in Old Town Key...
    See all reviews
    About this property
    Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (2)Excellent
    0.3 kilometres from Duval Street
    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 22 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Down Island Digs ~ Weekly Rental1 / 14
    (9)Very good
    0.2 kilometres from Duval Street
    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 29 November 2017
    This is such a cute and cozy home in a great location! The house is perfect for 3 people or less. The kitchen/den have limited space so it can get crowded with everyone...
    Reviewed 24 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...
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 20
    (2)Excellent
    0.2 kilometres from Duval Street
    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 22 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.3 kilometres from Duval Street
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    Duval Penthouse1 / 24
    (24)Very good
    0.1 kilometres from Duval Street
    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 26 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Key West Seashell Cottage-1 block to Duval, spa1 / 17
    (42)Excellent
    0.2 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2017
    Seashell cottage has become our home away from home in Key West. Great location, close but not too close. Within walking distance of restaurants, bars and all that happens...
    Reviewed 9 August 2017
    We were welcomed by Barbara, she was so nice and kind. This was a birthday gift to me from my husband and what a gift it was . Barbara and Carolyn added to my birthday with a...
    See all reviews
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Make Enquiry
    Shipyard1 / 24
    (26)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This condo was perfect. It has everything you could need for your stay. I loved the front porch and the back deck. It was private and the Annex was very well maintained. All...
    Reviewed 13 July 2017
    Nice and clean accommodations. Would stay again. Only one drawback, parking situations. Have a reserved spot but occupied by another tenant and squabble between security and...
    See all reviews
    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Bahama House1 / 24
    (26)Very good
    0.1 kilometres from Duval Street
    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 15 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    0.1 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Coral Condo1 / 25
    (10)Excellent
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    The location is perfect, a short block from Duval St. There is a grocery store just around the corner so we could carry everything back to our place. The house is cute and cozy...
    Reviewed 12 April 2017
    Great location, enjoy the verandah and the walkability of this location. Great restaurants nearby as well as a grocery store with a good deli. Condo is a nice size, attractively...
    See all reviews
    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New! Solaris Cottage Garden, located on one of Key West most private slow lanes, and is a Bohemian Dream!. Perfect for a couple or single guest ready to explore all that Key West has to offer! This unique vacation rental just completed renovation December 1st 2016! All new furnishings and...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Secret Courtyard Cottage ~ Weekly Rental1 / 9
    (6)Very good
    0.1 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2016
    Everything was as advertised. The location was great and since the cottage sits back a bit from the road it was nice and quit at night. We had one plumbing problem (that could...
    Reviewed 1 March 2016
    I wanted to keep this little piece of paradise a secret, but I guess I can't. This is much better than a motel, and much cheaper. A wonderful little home equipped with...
    See all reviews
    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Campbell Suite1 / 23
    (15)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    Staying at the Campbell Suite is like coming home. We have plenty of room to relax after a day of seeing the sights of Key West. The location is perfect. We can walk to all of...
    Reviewed 13 December 2016
    We rented this condo for a week from Historic Hideaways. Tim was great to work with. The condo itself is very nice and some upgrades have been made from the photos. It was...
    See all reviews
    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Grande Dame Key West - 'The Watson House' ~ Weekly Rental1 / 38
    (10)Very good
    0.2 kilometres from Duval Street
    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    From booking to our stay everything was flawless. The house is amazing for large groups and centrally located one block off Duval. The home is beautifully appointed and the...
    Reviewed 4 July 2016
    We had 7 couples and 2 singles for 16 people total. There was plenty of room for everyone. Upon arrival we found the house to be in very good condition, clean, and stocked...
    See all reviews
    About this property
    Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    Shipyard 253 - 2 Bedroom Condo with a Shared Pool1 / 10
    (41)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 November 2015
    We enjoyed our stay at Shipyard 253. It is a nice two bedroom/one bath with a great location only two blocks from Duval and situated in the middle of the strip. Was very...
    Reviewed 25 June 2013
    Stayed at the Shipyard 253 and had a wonderful time. Very nicely decorated, comfortable and a great location - just 2 blocks from Duval St. I would stay there again!
    See all reviews
    About this property
    7 night minimum stay condo upstairs unit with 2 bedrooms and 1 Bathroom upstairs spacious unit with 1 queen, 2 twins and 1 pullout sofa. . The unit comes with one assigned parking spot. There is alot to see and do in historic Key West. Enjoy touring noted Key West attractions including the...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Key West Casa1 / 24
    (26)Very good
    0.3 kilometres from Duval Street
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    We just recently returned from our stay in Key West Casa. This condo has everything you need. We did not use the bikes because we did not know how to unlock them, but we never...
    Reviewed 12 June 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
    See all reviews
    About this property
    KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and walking distance to shopping,...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Penthouse On Duval ~ Weekly Rental1 / 20
    (10)Very good
    0.1 kilometres from Duval Street
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 October 2016
    A group of friends and I came down for my bachelor party and couldn't have asked for a better set up. The place is massive, more than enough room for everybody to get either a...
    Reviewed 2 July 2015
    We stayed at Penthouse on Duval for a week, renting the entire unit (4 Bedrooms and 4 1/2 baths) and it was absolutely as described including the pictures. It was large...
    See all reviews
    About this property
    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    ~ CLOUD 9 ~ Heavenly Home In Perfect Location w/ Heated Pool & Parking1 / 27
    (16)Excellent
    0.2 kilometres from Duval Street
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Everything Key West is right outside the courtyard door! Less than one block from Duvall St. All the best restaurants and bars with great live music are within walking distance...
    Reviewed 30 March 2017
    This place was absolutely perfect! Steps from all the action of Duval and yet, amazingly, you couldn't hear anything but nature when sitting by the pool! The house was...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Key West Wabi Sabi ~ Weekly Rental1 / 31
    (3)Very good
    0.2 kilometres from Duval Street
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Great house, pool is awesome, location is perfect right next to grocery store and 1/2 block off Duval. Very quaint inside and out!
    Reviewed 28 December 2014
    We stayed here for a week over Christmas with 4 adult kids and had the best time ever. The accommodations were great for 6 of us and we couldn't ask for a better location...
    See all reviews
    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof....
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Breezy Bungalow1 / 24
    (1)Excellent
    0.3 kilometres from Duval Street
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    ~ MARTHA TRUMAN SUITE ~ Luxury Apt w/ Pvt Balcony, Steps to Duval St & Beach1 / 24
    (2)Excellent
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2017
    Right around the corner from Duval street, The Hemingway house, and some little light house. The property manager, Danny, was very helpful. He was able to give us coupons for...
    Reviewed 18 September 2016
    Had a great time as we truly relaxed after our wedding and enjoyed the best of Key West with bicycling, walks, food tours and being together. Historic Key West Rentals was...
    See all reviews
    About this property
    THE MARTHA SUITE 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...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    0.1 kilometres from Duval Street
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cleverly hidden from view at the end of a narrow island urban lane that intersects with downtown Duval Street, this Starlight Siesta vacation rental encompasses the rear half of the Key West penthouse property known as Penthouse On Duval. Perfectly staged in the island's city center, this...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    ~ SEAS THE DAY ~ Cute Condo w/ Parking & Pool Walk to Shops, Beach, Nightlife1 / 29
    (2)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Internet Access
    • Washer
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    We spent 2 weeks in this apartment. Clearly, the location is ideal. It is walkable to almost everything of interest in Key West -- museums, theaters, restaurants, Mallory...
    Reviewed 9 May 2016
    We had a very enjoyable week stay in Key West. Seas The Day is a very nice condo in the Shipyard area of Truman Annex on the western end of Key West. The condo was very clean...
    See all reviews
    About this property
    The 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
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Shipyard Treasure1 / 26
    (52)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • DVD Player
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    Shipyard Treasure is welcoming, comfortable, condo, decorated with Key West art in the bedrooms, living room, and entry, and with wonderful beds, bedding, and much better than...
    Reviewed 16 March 2013
    My family had a wonderful vacation while staying at the Shipyard Treasure. The condo was tastefully decorated and was stocked with all the comforts of home. The location was...
    See all reviews
    About this property
    SHIPYARD TREASURE: Contemporary Condo at Truman Annex - Walk to Beach/Duval Street Decorated in casual contemporary style, this second floor Shipyard condo is centrally located in the Truman Annex, within quick walking distance to all the sites and attractions of Old Town Key West. Relax in 2...
    View all property information
    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    ~ Poinciana Garden ~ Quiet Condo w/ Pvt Hot Tub & Parking In Perfect Location1 / 25
    (3)Very good
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Hot Tub
    • Grill
    • Parking
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    This is a very nice little apartment. It is clean and efficient. The location is great for walking to lots of the attractions of Key West, even though it's in a quiet...
    Reviewed 29 March 2017
    This is a very small place with a great location. The private hot tub is an added benefit. The biggest negative is the kitchen. It is tiny, with old cabinets and lots of ants...
    See all reviews
    About this property
    The Poinciana Paradise Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The Garden at Poinciana Place is a cozy and...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.1 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Would you enjoy truly modern luxury within walking distance to Key West's best restaurants, clubs, and art galleries? If so, this is the vacation house for you! We are set within Key West's Historic District, a block from famous Duval Street, 2 1/2 blocks from the Hemingway House, 7 blocks to...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1
    List your property
    Owner log in