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$750

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Southard Street Queen Conch - A Historic compound with large sunny pool

Key West house
4 BR / 4 BA / Sleeps 8 | Quick view
Excellent27 Reviews

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(27)

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, …
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(27)

What a lovely property

Left on Jun 18, 2009 for a stay in May 2008

This is a great home in a great location. All of the rooms are wonderfully furnished and clean. The backporch and sun deck are truly amazing and relaxing. I especially enjoyed the privacy of the pool and backyard for relaxing and resting. I would stay here again over and over again.

$450

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Villa Paradiso: A unique mid-town paradise

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent35 Reviews

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Reviews

(35)

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavillion with an ornate…
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(35)

The 3 couples loved this home.

Left on Jun 18, 2009 for a stay in February 2009

We chose the Villa because it advertised 3 bedrooms and 3 baths. I would advertise it as 2.5 bedrooms. However, the space worked out very well for the 6 of us. The home is graciously appointed and easy to live in. The small pool area was a perfect gathering spot. There were other decks and seating areas when each of us choses a bit more privacy. The Villa was within walking distance of the …

$240

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Ann Street Cottage: A bright and airy home near Duval Street

Key West cottage
1 BR / 2 BA / Sleeps 2 | Quick view
Excellent47 Reviews

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Reviews

(47)

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. Within 2 blocks you'll …
  • Shared outdoor pool (unheated)
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  • Suitable for children - ask
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(47)

Nice

Left on Jun 18, 2009 for a stay in July 2006

My husband and I stayed at the ann street cottage. It is a nice cozy house. Nice size bedroom, and a equipped kitchen to make your own dinners. We went shopping for groceries and made a nice dinner every night--saved a ton on eating out. The cottage was quiet, and clean--there is also a nice private outdoor back patio area. There is also a nice community pool. Only drawback was that the tv …

$370

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Whitehead House: A unique two story home beside the Audubon House

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent42 Reviews

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Reviews

(42)

Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1 space for normal-…
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(42)

Hidden Jewel

Left on Jun 18, 2009 for a stay in July 2008

This house is fantastic! The location is awesome - right in the middle of everything!!! Everything you would want was there. House was clean, pool was excellent and off street parking is great! The 2 bedrooms and bathroom downstairs are small, but for the amount of time you really need them, they are fine. I would certainly recommend this house and plan to rent it again.

$240

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Ann Street Tranquility: A cozy and peaceful cottage

Key West cottage
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent48 Reviews

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Reviews

(48)

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 Joe's, and Hog's Breath …
  • Shared outdoor pool (unheated)
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(48)

Ann Street

Left on Jun 18, 2009 for a stay in May 2007

We enjoyed the cottage. The interior was beautiful and very clean. Very nicely decorated with higher end accessories. The location was absolutely perfect. The only improvement that could be made was the entrance and pool area was not well manicured. It was very overgrown and jungle like. We would not hesitate to return.

$1,000

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DREAMING ON DUVAL- Luxury 5 Bed & Private Pool- As seen on HGTV House Hunters

Key West house
5 BR / 4 BA / Sleeps 12 | Quick view
Excellent20 Reviews

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Reviews

(20)

Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to offer and accommodates …
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(20)

Fabulous...

Left on May 24, 2010 for a stay in May 2010

Dreaming in Duval is a beautiful, spacious home. The home is very well equipt,and accomodated 10 people easily.
The location was perfect, we could walk to everything.
Dean and Paul were both great and very helpful.
One of our best vacations ever, we are already planning a return trip.

$470

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Coconut Cabana: A restored Old Town home with charm & tropical ambience

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent38 Reviews

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Reviews

(38)

An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story historic home is …
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(38)

Coconut Cabana - Go Nuts!

Left on Jun 18, 2009 for a stay in November 2007

We loved Coconut Cabana! This house was perfect for a "sibling celebration" of my brother's 50th birthday. The house was darling, well equiped and the entire rental process was smooth sailing. There is no place like Key West and this house just off Duval was just where we needed to be. We would highly recommend!

$320

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Havana Lane: A classic conch cottage with rustic charm

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent30 Reviews

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Reviews

(30)

Thoughtfully restored, Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally …
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(30)

Gorgeous surroundings, comfortable Key West home

Left on Jun 18, 2009 for a stay in April 2009

As soon as we unlocked the gate to the high wooden fence surrounding 1
Havana Lane, we knew we had picked a gem of a place to stay for Spring Break.
My husband and I came to Key West with our 15 year-old daughter and her
friend. The home was perfect for us four, and we enjoyed being there almost
as much as going out and about the island. We called the yard our "Secret
Garden." It was so lush…

$320

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Catherine House: A charming Old Town Key West cottage

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent37 Reviews

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Reviews

(37)

This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably sleep four and …
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(37)

Cozy spot in perfect location

Left on Jun 18, 2009 for a stay in March 2009

Catherine House is truely a shotgun house -- long and narrow -- but has been renovated into a cozy and lovely little two-bedroom. The beds are large and comfy, with two full baths perfect for two couples. The kitchen is basic, but open to the living area and more than sufficient for vacation meals. The pool is more like a tub, but is fine for toddlers and tired parents who want to dip their …

$239

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1/2 Block to Duval, World of its own -Nassau Suite

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent6 Reviews

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Reviews

(6)

The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an endless party, The …
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(6)

Wish I had found this place 15 years ago.

Left on Jan 06, 2014 for a stay in December 2013

Stayed in the Nassau the week of Christmas thru New Years. Came down with two other couples. The pictures do not do this place justice. Plenty of room for all. Having two bathrooms was also a plus. Very close to Duval street, and anywhere you really would want to go is in walking distance, minus the beach, but is a short/cheap taxi ride away. Our unit had 90% new furniture, and matresses. …

$850

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Villa Tropicale: A lush, secluded estate in the Casa Marina District

Key West house
4 BR / 4 BA / Sleeps 8 | Quick view
Excellent15 Reviews

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Reviews

(15)

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of mature palms, birds of …
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(15)

The coolest house ever!

Left on Jun 18, 2009 for a stay in November 2008

I would highly recommend this property to anyone looking for a place to stay in Key West with a group of friends. It offers the best of both worlds....You could never leave the property and have a wonderful time or a quick cab ride and you're at Duval Street. Our group ventured off on a day trip to the Dry Tortugas, which was set up by the properties conceier service...and that was awesome...…

$290

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Beach Club #204 - Unique Oceanfront living

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent14 Reviews

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Reviews

(14)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This is one of the most elegant and colorful 2 bedroom units in the Key West Beach Club. It …
  • Ocean or water views
  • Shared outdoor pool (unheated)
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(14)

Great Time

Left on Jun 18, 2009 for a stay in May 2008

I just wish I had the money to buy a condo at The Beach Club. It's the second time I've stayed there and each time was perfect.

$173

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Elizabeth Retreat: A three bedroom historic home in Old Town

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
Very Good3 Reviews

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Reviews

(3)

30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly restored eyebrow 3 …
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(3)

A month in Key West

Left on Jun 18, 2009 for a stay in January 2009

We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful - really stayed on top of everything and went out of their way to accomodate our schedule on check in and check out. The house was absolutely lovely and clearly well cared for. We liked it so much, we are coming back …

$270

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Key Lime Calypso: A cottage in the heart of Bahama Village

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view
Very Good43 Reviews

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Reviews

(43)

The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this two bedroom cottage…
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(43)

Lovely cottage and great location

Left on Jun 18, 2009 for a stay in September 2008

The cottage was a great "get away from it", but yet was right in the heart of the main area Key West, just off Duval St. As the property was centrally located along Duval St, it was also quiet and peaceful. The private pool was great to have and the garden had a lovely sunny aspect, but there was enough shade to get out of the sun if you wanted too. The pool was welcome as the main beaches on the…

$270

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Pete's West Cottage steps from Duval

Key West cottage
2 BR / 1 BA / Sleeps 4 | Quick view
Average2 Reviews

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Reviews

(2)

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
  • Shared outdoor pool (unheated)
  • Internet Access
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  • Suitable for children - ask
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(2)

Nice but could use some sprucing up

Left on Oct 13, 2014 for a stay in October 2014

Nice place. Quiet location. I would have thought someone might clean the pool during our stay since the iguanas in the trees used it for their bathroom quite frequently

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$127

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South Street Cottage: Bright & sunny in the Casa Marina district

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

30 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights, light tile floors and …
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1 / 17

$113

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Mango Menagerie: A treasury of island colors and Key West charm

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

30 DAY MINIMUM RENTAL Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite Flaming Buoy restaurant. The property is …
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$280

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Namaste : A blissful one bedroom cottage designed with relaxation in mind.

Key West house
1 BR / 2 BA / Sleeps 2 | Quick view

Details

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
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$200

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Eliza's Jewel is a charming property close to White Street.

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

30 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 architecture with …
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1 / 12

$580

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Tucked away near the Southernmost Point, Louisa's Hideaway is it!

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined path that leads to …
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1 / 13

$270

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Pete's East Cottage: Cypress east cottage steps from Duval

Key West cottage
2 BR / 1 BA / Sleeps 4 | Quick view

Details

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 4

$215

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Key West Hyatt Windward Pointe

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping. This unit rents …
  • Ocean or water views
  • Hot Tub/Jacuzzi
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  • Smoking allowed - ask
  • Suitable for children
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$540

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Casa de Cuba:Beautiful home loaded with style and elegance

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored and used as …
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1 / 28

$470

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Pete's Cottages: Twin Cypress cottages steps from Duval

Key West house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

$400

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Fantastic 1800 Atlantic Penthouse - C424

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared. The Master Bedroom has king bed, The guest bedroom has a queen and the living room has a queen pull-out sleeper sofa. High speed interent available. There is a full size fully …
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (1)

    Great mini vacation!!

    Left on Sep 09, 2010 for a stay in July 2010

    The condo we stayed in had obviously been remodeled. It was gorgeous with plenty of space for 4 people! Also, the pool and jacuzzi were huge! We really enjoyed the accomodations of the condo so much we could've stayed in the room the whole 4 days! Even though it was not within walking distance to Duval street, the island is very small. You can rent a scooter for the day and tour the entire …

    $300

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    1800 Atlantic Key West 2 bedroom garden-view A307

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent3 Reviews

    Details

    Reviews

    (3)

    Great 3rd floor 2 bedroom 2 bath rental unit at 1800 Atlantic. All furnishings replaced in 2011,decorated in an elegant contemporary style. This unit is spacious with a full size fully equipped eat in Kitchen. There is a king bed in the master bedroom, 2 twin beds in the 2nd bedroom and a queen sleeper sofa in the …
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      Reviews

      (3)

      Beautiful and spacious, highly recommend!

      Left on Sep 10, 2010 for a stay in June 2010

      Unit was clean and spacious, and very well equipped. Staff very helpful - no problems, but very responsive!

      $400

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      Two Bedroom Premiere Ocean-View C438

      Key West condo
      2 BR / 2 BA / Sleeps 4 | Quick view
      Very Good1 Reviews

      Details

      Reviews

      (1)

      This is a beautiful top floor two bedroom ocean-view unit at 1800 Atlantic. It is an extra large floor plan with expansive views You cannot get a better view than this. There is a full size fully equipped eat in Kitchen. Full size washer & dryer. Both bathrooms were renovated in 2013. The bedroom's and living room …
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Washing Machine
      • Balcony or terrace
      • Suitable for children - ask
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      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Very relaxing tropical stay, close to Smathers Beach

      Left on Sep 18, 2010 for a stay in December 2009

      December 2009 was our fifth time staying at the 1800 atlantic condo. My husband and I are anticipating our stay this year as it is the best value for our dollar. Julia at all Florida Keys Property Management is a pleasure to deal with when making reservations. Any questions or concerns with the unit when we have arrived, have always been handled promptly. The condo is close to Smathers Beach …

      $133

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      Casa Manana 2 bedroom Cottage in Old Town Key West

      Key West house
      2 BR / 2 BA / Sleeps 6 | Quick view
      Excellent8 Reviews

      Details

      Reviews

      (8)

      THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from Faustos grocery, Sandy…
      • Wireless Internet
      • Washing Machine
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      • A/C or climate control
      • Patio
      • Suitable for children - ask
      • Suitable for the elderly

      Details

      Reviews

      (8)

      Perfect Location

      Left on Sep 10, 2010 for a stay in June 2010

      We visited Key West with another couple for a week in June. We were extremely please with the charming home we stayed in. Has everything you could possible need. Perfect location, minutes from Duval Street, was great we walked everywhere. We plan on coming back next year and hope to rent the home again. Thanks all Florida Keys for making our stay so memorable!

      $200

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      Céad Míle Fáilte - Truman Annex

      Key West condo
      2 BR / 1 BA / Sleeps 4 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      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 home across the pond. We know you will enjoy your time in Key West as much as we …
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (3)

      Great Location

      Left on Sep 11, 2010 for a stay in August 2009

      The accommodation was very clean, spacious, and with an incredible location close to down town and local grocery shops. Renting this property was a great decision as it comes with access to swimming pool which was great for the kids.

      $300

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      1800 Atlantic Condominiums Key West C327

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view
      Average4 Reviews

      Details

      Reviews

      (4)

      Fabulous spacious two bedroom condominiums, directly on the Atlantic Ocean in Key West Florida. The Condo is fully equipped with a full size Kitchen. There is also a full size washer & dryer for your convenience. All rooms have a color cable TV and the unit has high There is an extensive private balcony that can …
        • Suitable for children - ask
        • Suitable for the elderly
        • Wheelchair accessible

        Details

        Reviews

        (4)

        Key West

        Left on Oct 31, 2010 for a stay in October 2010

        The explanation & photos on the internet were not all true. I booked this condo expecting to be able to use the beach. But the beach was not accessible. The security guard said that the last time the beach was nice was about 5-6 yrs ago. So, we had to drive downtown to a park and pay to use the public beach. There's alot of traffic 24/7. There were workers on-site re-doing the hallway walls so …

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        $217

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        Historic Hideaway Olivia Retreat Key West

        Key West cottage
        2 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Look no further you have found a beautiful 2 bedroom 2 bath "Shot-Gun" house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining table in the …
        • Washing Machine
        • Outdoor Dining Area
        • A/C or climate control
        • Patio
        • Books
        • Suitable for children
        • Suitable for the elderly - ask
        1 / 8

        $2,500

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        Downtown Tree Top Studio

        Key West condo
        1 BR / 1 BA / Sleeps 2 | Quick view

        Details

        MONTHLY RENTAL ONLY Fantastic 2nd floor studio with a large private deck located just one block from famous duval street. This tree top studio is cozy. For your convenience there is a kitchennette with a 2 burner stove, microwave oven and a toaster oven. There is a brand new queen size sleeper sofa and of course the …
        • Internet Access
        • Housekeeping Optional
        • Outdoor Dining Area
        • A/C or climate control
        • Deck
        • Pet friendly - ask
        1 / 13

        $4,500

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        Lighthouse View Cigar Makers Cottage Key West

        Key West condo
        2 BR / 1 BA / Sleeps 4 | Quick view

        Details

        This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the famous Key West …
        • Internet Access
        • Housekeeping Optional
        • Washing Machine
        • Clothes Dryer
        • A/C or climate control
        • Pet friendly - ask
        • Suitable for children
        • Suitable for the elderly
        1 / 13

        $117

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        1800 Atlantic fabulous 3rd floor condo unit

        Key West condo
        2 BR / 2 BA / Sleeps 6 | Quick view

        Details

        This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the length of the unit. The unit is tiled throughout with a full size fully equipped eat in Kitchen. There is also a full size washer dryer for your convenience. Both bedrooms and the living room have TV's. …
          • Pet friendly - ask
          • Suitable for children
          • Suitable for the elderly - ask
          • Wheelchair accessible - ask

          $230

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          Royal Palm

          Key West house
          2 BR / 2 BA / Sleeps 5 | Quick view
          Very Good2 Reviews

          Details

          Reviews

          (2)

          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 offers privacy and …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Central heating
          • Suitable for the elderly - ask

          Details

          Reviews

          (2)

          Really Great Experience

          Left on Mar 15, 2013 for a stay in February 2013

          Had a great time. Historic Hideaways was very helpful. Our place was central to everything, very clean. Perfect for our needs.

          Thank you.

          $255

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          Banana Key

          Key West condo
          2 BR / 2 BA / Sleeps 4 | Quick view
          Excellent3 Reviews

          Details

          Reviews

          (3)

          Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just steps from the Gulf …
          • Ocean or water views
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (3)

          Better than the pictures!!!

          Left on Jan 11, 2012 for a stay in December 2011

          We absolutely loved the apartment and the fantastic walk behind the apartment that lead to Duval Street. If we could retire in Key West, this apartment is perfect. The master bedroom was so private, we barely noticed our two daughters in their room. The only complaint would be that the internet signal was weak and we a few problems with that.

          $183

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          Blackbeard's Treasure - MONTHLY Rental (30 night min.)

          Key West house
          3 BR / 3 BA / Sleeps 8 | Quick view
          Excellent1 Reviews

          Details

          Reviews

          (1)

          SPRING SPECIALS! 10% off MAY & JUNE 2015! Please see Specials Page for terms, rules and limitations. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water…
          • Ocean or water views
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • Suitable for the elderly - ask

          Details

          Reviews

          (1)

          Beautiful condo.

          Left on Apr 28, 2015 for a stay in February 2015

          We very much enjoyed this condo. It is beautifully decorated and there is a high priority for safety. Each condo has a private elevator that can only be entered with a specific fob. The roof-top dipping pool was wonderful on those really hot days. We enjoy laying in the sun & it was nice to be able to dip in the pool from time to time. We walked everywhere we chose to go, it's wonderful …

          $400

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          Casa Camilla

          Key West house
          2 BR / 2 BA / Sleeps 4 | Quick view
          Excellent11 Reviews

          Details

          Reviews

          (11)

          You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the property is beautifully …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (11)

          absolutely gorgeous!

          Left on Dec 07, 2011 for a stay in November 2011

          The house is absolutely beautiful and in a great location; easy to get to Duval street. Very quiet neighborhood. The house had everything except internet access and a heated pool/jacuzzi.

          $700

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          Admiral's Lane

          Key West house
          4 BR / 3 BA / Sleeps 8 | Quick view
          Excellent15 Reviews

          Details

          Reviews

          (15)

          As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere gated waterfront …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (15)

          Excellent experience

          Left on May 11, 2010 for a stay in March 2010

          Beautiful accommodations, helpful and friendly staff, and excellent experience
          overall. Highly recommend both the house and the management company.

          $286

          Inquire

          Havana Hideaway

          Key West condo
          2 BR / 2 BA / Sleeps 5 | Quick view
          Excellent10 Reviews

          Details

          Reviews

          (10)

          Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure …
          • Ocean or water views
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • Suitable for the elderly - ask

          Details

          Reviews

          (10)

          Week in Paradise

          Left on Jan 16, 2013 for a stay in December 2012

          This was one of the greatest stays that we have had. Condo was within walking distance to everything block to most. Very nice place to stay. Easy check in and check out process. This place has a great view from pool. We were here in December with about 80 degree temps each day so we shut down the air and had the doors open most of the time the only draw back to this is the chickens will wake…

          $275

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          Casablanca

          Key West villa
          1 BR / 1 BA / Sleeps 3 | Quick view
          Excellent25 Reviews

          Details

          Reviews

          (25)

          This gracious one bedroom, one bath conch cottage with private pool is the perfect place for your dream vacation. Casablanca is set back from White Street which runs the fourteen-block width of the island from the Gulf of Mexico to a fishing pier jutting out into the wide Atlantic Ocean. The street, named after …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly

          Details

          Reviews

          (25)

          Good Times!!

          Left on Sep 23, 2008 for a stay in September 2008

          This was one of my most pleasent vacation rental experiences I have ever had. Even though we got the boot for hurricane Ike we got back in our car and drove right into town as soon as we were aloud. With the quiet neighborhood and the private pool, the location to downtown and private parking was just the icing on the cake. My wife and ten month old baby had a wonderful time and would …

          $286

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          Foundry's Corner

          Key West house
          2 BR / 2 BA / Sleeps 4 | Quick view
          Excellent22 Reviews

          Details

          Reviews

          (22)

          Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was built around 1845 as …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (22)

          Awesome Hideaway

          Left on Nov 19, 2008 for a stay in October 2008

          I was absolutely thrilled with this property, the townhouse was well appointed and beyond comfortable. The location cant be beat as its just a minutes walk to the north end of Duval St. and all its bars and restaurants. We were there for Fantasy Fest and having a secluded, quiet place to come back to away from all the madness that is FF was quite wonderful. I suppose if I had to rate this …

          $350

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          Poinciana House

          Key West house
          1 BR / 2 BA / Sleeps 4 | Quick view
          Excellent40 Reviews

          Details

          Reviews

          (40)

          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 back and forth, you can…
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (40)

          Awesome pool and patio, flowers everywhere!

          Left on Aug 15, 2008 for a stay in June 2008

          I can't say enough about how beautiful this property is. Lots of flowers, the Royal Poinciana tree is very unique. The pool is awesome and the patio on the back of the house leads right into the pool. The decor is very Key West and I loved it. We did have one problem, the AC went out in the living room/kitchen area ON MY WEDDING DAY! There is an AC unit in the bedroom that still worked. It …

          $215

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          Ann Street Gardens

          Key West cottage
          1 BR / 1 BA / Sleeps 3 | Quick view
          Excellent43 Reviews

          Details

          Reviews

          (43)

          (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 offers the …
          • Shared outdoor pool (unheated)
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • Suitable for the elderly - ask

          Details

          Reviews

          (43)

          The Great Escape

          Left on May 02, 2009 for a stay in March 2009

          Location, Location, Location: One block from Duval Streets north end, three blocks to Mallory Square, The Westin,The Hyatt and Pier House, Historic Seaport Boadwalk, multiple wonderfull musuems. No need for any form of city transportation. The best of Key West is 10 minutes(at most)away by foot..even a beautiful public beach at the end of Simenton, two well equiped grocery stores and a …

          $189

          Book

          Beautiful Island Style Cottage

          Key West house
          1 BR / 1 BA / Sleeps 4 | Quick view
          Excellent7 Reviews

          Details

          Reviews

          (7)

          Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share an affinity for Key…
          • Internet Access
          • Housekeeping Optional
          • Outdoor Dining Area
          • A/C or climate control
          • Deck
          • Pet friendly
          • Suitable for children - ask
          • Suitable for the elderly
          • Wheelchair accessible - ask

          Details

          Reviews

          (7)

          Very cozy cottage

          Left on Aug 03, 2012 for a stay in May 2012

          Very cozy cottage, with all the comforts of home. The cottage had everything you needed. Pots, pans, plates,flatware, coffee cups, nice wine glasses, coffee maker, toaster. Name it's there. It was like a home away from home.

          $400

          Inquire

          The Meadows House

          Key West house
          2 BR / 2 BA / Sleeps 6 | Quick view
          Excellent19 Reviews

          Details

          Reviews

          (19)

          If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around residency, relatively …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (19)

          Week In Key West

          Left on Aug 16, 2011 for a stay in July 2011

          The house was very nice, the back yard/pool
          were great...Enjoyed it very much.
          Check in & out very easy.

          $600

          Inquire

          Kemp House

          Key West house
          3 BR / 3 BA / Sleeps 6 | Quick view
          Excellent10 Reviews

          Details

          Reviews

          (10)

          This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary …
          • Wireless Internet
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (10)

          very lovely

          Left on Feb 09, 2009 for a stay in November 2008

          Beautiful house. Near everything. Comfortable and well kept.

          $250

          Inquire

          Rose Cottage

          Key West house
          1 BR / 1 BA / Sleeps 2 | Quick view
          Excellent70 Reviews

          Details

          Reviews

          (70)

          Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way, the lane intersects…
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for the elderly - ask

          Details

          Reviews

          (70)

          Great Getaway Spot

          Left on Sep 23, 2008 for a stay in April 2008

          I am working in Iraq and had just a short time for a break, dreamt about a place with a pool down in the Keys.
          This location sounded great - and it lived up to our expectations. Everything worked, it was spotless, it had all the amenities, it was completely private and just a short walk from the main street of Key West. Outstanding location. The back yard was great, there were no bugs, the ladder…

          $215

          Inquire

          Coral Condo

          Key West condo
          1 BR / 1 BA / Sleeps 4 | Quick view
          Excellent3 Reviews

          Details

          Reviews

          (3)

          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 the second floor of…
          • Internet Access
          • Outdoor Dining Area
          • A/C or climate control
          • Porch
          • Garden

          Details

          Reviews

          (3)

          Paradise

          Left on Oct 05, 2013 for a stay in September 2013

          Beautiful condo...paradise away from home. Not one complaint. Well managed & maintained. Def recommend to anyone headed to Key West.

          $700

          Inquire

          Truman House

          Key West house
          4 BR / 3 BA / Sleeps 10 | Quick view
          Excellent11 Reviews

          Details

          Reviews

          (11)

          The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located on an upscale and …
          • Hot Tub/Jacuzzi
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • Suitable for the elderly - ask

          Details

          Reviews

          (11)

          Extremely comfortable house in a great neighborhood

          Left on May 13, 2011 for a stay in February 2011

          The Truman house is an extremely comfortable house in a great neighborhood. We rented the house two years in a row for three months. We loved the huge heated pool and the privacy afforded by the landscaping. The location gives you the opportunity to enjoy some of the best restaurants in Key West, all within walking distance. While only a few blocks from Duval Street, you are far enough away to …

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