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$249

3 BR / 2 BA / Sleeps 8

11 Reviews

$249

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Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West condo
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent11 Reviews

Details

Reviews

(11)

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 charm found only in …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(11)

Amazing location!!!

Left on Nov 05, 2013 for a stay in August 2013

Location was wonderful one block block of Duval street, 3 of us shared the rental each had their own bedroom and there were 2 baths, and we 3 grown men having the 2nd bath was very valuable. The backyard area while not being the most beautiful thing in the world was still a great place to sit out and have a few drinks with friends old and new, our upstairs neighbors were great people and we …

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$288

3 BR / 2 BA / Sleeps 6

Southernmost Retreat- 1 Block from Duval - Key West vacation rentals
1 / 10

$288

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Southernmost Retreat- 1 Block from Duval

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

Details

Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in the center of the Old…
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$558

3 BR / 3 BA / Sleeps 5

1 Reviews

$558

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Ocean Retreat

Key West condo
3 BR / 3 BA / Sleeps 5 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the beach. Only three …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Ocean Retreat- luxe comfort without pretense!

Left on Feb 28, 2014 for a stay in February 2014

This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded all our expectations. The new pictures are accurate representations of the condition and quality of the property. Tasteful and yet relaxed, this is, without a doubt, our favorite condo in our eight years of vacationing in …

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$743

3 BR / 4 BA / Sleeps 8

Ocean Paradise - Key West vacation rentals
1 / 25

$743

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Ocean Paradise

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

Details

Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing available as well. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$300

3 BR / 2 BA / Sleeps 8

1 Reviews

$300

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Oceanside Key West's Best Luxury Penthouse Condo

Key West condo
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities are rounded out with …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(1)

Awesome View. Great Place.

Left on May 01, 2015 for a stay in April 2015

My brother, mother and I and our spouses met up in Key West for a great vacation. This condo had plenty of space inside and out for 6 adults and was very comfortable. The deck offered a wonderful view for morning coffee, nap, conversation, and/or book read each and every day. The pool space was also great. This condo is technically on Stock Island which is on the opposite end from THE Duval …

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$286

3 BR / 3 BA / Sleeps 6

A Dream come True - Key West vacation rentals
1 / 10

$286

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A Dream come True

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

Details

******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a balcony off the master …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children

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$353

3 BR / 2 BA / Sleeps 8

8 Reviews

$353

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Hemmingway's Retreat

Key West house
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home Furnishings. The …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (8)

    1211 Catherine St.

    Left on May 10, 2010 for a stay in April 2010

    My wife and I spent time in April at 1211 Catherine St., Key West, FL and had a marvelous time. The house is wonderful expecially the private pool. All that Key West has to offer is within easy walking or cycling distance of the house. The house is beautifully furnished and appointed so much so we spent many days just staying home and relaxing around the pool. One of the bicycles provided had to…

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    $375

    3 BR / 3 BA / Sleeps 6

    5 Reviews

    $375

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    3 Bedroom Yacht On The Atlantic Ocean

    Key West yacht
    3 BR / 3 BA / Sleeps 6 | Quick view
    Excellent5 Reviews

    Details

    Reviews

    (5)

    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around town or shopping, eating and drinking your way down the famous Duval St. You may just want to stay on board and enjoy a …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Great place to relax with sunshine and water

    Left on Sep 20, 2012 for a stay in August 2012

    Loved the yacht Quest. It was docked in a really nice oceanfront marina. The parking was free, safe and just a few steps to the boat. My bed was so comfortabe and the a/C's worked real well. I had the best nights sleep. The owners Bob and Kimberly have been in Key West for 25 years and they are very helpful and honist on what to see and what to do. If you have never stayed on a yacht I highly …

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    $349

    3 BR / 2 BA / Sleeps 8

    5 Reviews

    $349

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    Key West 'Yacht And Breakfast!'

    Key West yacht
    3 BR / 2 BA / Sleeps 8 | Quick view
    Excellent5 Reviews

    Details

    Reviews

    (5)

    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig coffee, 3 burner …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Wireless Internet
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Key West - Yacht Style

    Left on Jan 12, 2015 for a stay in December 2014

    It never crossed my mind to look into staying on a Yacht in Key West. Now, everywhere we travel it is our first option. The boat accommodations were perfect for us. We could fish right off the docks, paddle the kayaks around the marina, and bike around town. Front Street and Duval were only steps from the marina. Staying on this boat made our trip better than we could have ever imagined. We were …

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    $350

    3 BR / 2 BA / Sleeps 6

    1 Reviews
    1 / 19

    (1)

    Poor

    $350

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    KEY WEST LIVIN' BEAUTIFUL 50' Yacht 3 Bed , 2 bath, WIFI, Flatscreen,Sleeps 6

    Key West houseboat
    3 BR / 2 BA / Sleeps 6 | Quick view
    Poor1 Reviews

    Details

    Reviews

    (1)

    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach , Heated Infinity -Edge …
    • Waterfront
    • Ocean or water views
    • Sauna
    • Internet Access
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Not worth your money: Falling apart and dirty.

    Left on May 18, 2015 for a stay in April 2015

    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels and beddings are dirty as well the seats, showers and the rest… No keys to lock it. We wanted to try "boat living" before buying a boat... The Marina is nice and quiet, 5 miles from Duval Street.

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    $185

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $185

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    Architects Cottage on Quiet Lane in Old Town

    Key West house
    3 BR / 2 BA / Sleeps 8 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Note, this is a monthly rental. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which will help make your…
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children

    Details

    Reviews

    (1)

    Tranquility and great music at night

    Left on Dec 08, 2014 for a stay in November 2014

    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at night. There is a little park at the end of the lane, and if you travel with a dog as I do, the park is a great place to meet other people and dogs. There is a large, light-filled room overlooking the pool in the …

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    $10,000

    3 BR / 2 BA / Sleeps 6

    2 Reviews

    $10,000

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    Ellen's Retreat, tropical living, MINIMUM 28 days

    Key West house
    3 BR / 2 BA / Sleeps 6 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is effortless with the design …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    A place in heaven!

    Left on Feb 19, 2013 for a stay in January 2013

    Ellen´s retreat was simply fantastic. The house was beautiful and luxurious. The grounds were spacious and it was like you had your very own private oasis. I need also to mention the fantastic and beautiful heated pool in which both children and adults spent most of their time.

    I will certainly come back again. I have never in my lift had such a great holiday stay.

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    $450

    3 BR / 2 BA / Sleeps 6

    8 Reviews

    $450

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    3 Bedroom Oceanfront Condo Key West

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

    Details

    Reviews

    (8)

    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at your fingertips. Sorry …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Suitable for children

    Details

    Reviews

    (8)

    Beautiful oceanfront condo

    Left on Jan 11, 2014 for a stay in January 2014

    We just rented this unit - it was wonderful!!! Beautiful kitchen,
    recently remolded. Large family room. Bedrooms nice sizes. Unit
    has a complete wrap around deck with ocean views. About 3 minute walk to Smathers beach. Really nice pool & 15 person hot tub. If you are
    a beach person this unit is for you!! Only negative - not that close
    to the down town area(5 minute car ride) - however unit …

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    $173

    3 BR / 4 BA / Sleeps 8

    3 Reviews

    $173

    Inquire

    Casa Alegria - a Bahamian style conch house

    Key West house
    3 BR / 4 BA / Sleeps 8 | Quick view
    Excellent3 Reviews

    Details

    Reviews

    (3)

    30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park bicycles. You can park…
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (3)

    paradise

    Left on Apr 24, 2014 for a stay in January 2014

    We were fortunate enough to stay in this immaculate and welcoming retreat. We loved swimming in the pool and riding the bikes around town. We could not have asked for a more perfect place to make our vacation more fabulous!!!! Love...love...love!

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    $193

    3 BR / 4 BA / Sleeps 6

    2 Reviews

    $193

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    Packer Retreat: A beautifully renovated "Conch" house

    Key West house
    3 BR / 4 BA / Sleeps 6 | Quick view
    Very Good2 Reviews

    Details

    Reviews

    (2)

    30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden area. Nicely decorated …
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Great house needs updating

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

    Packer retreat is a great house. So great I am renting it in 2010. The layout and outdoor space is unusually large for Key West. And the home is very private and quiet. the location is within walking distance to Duval and White streets.

    The home is beautifully decorated but needs to be "freshened" up. The sofas and carpets are dirty. the kitchen has very little equipment (1 pan, no serving…

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    $470

    3 BR / 2 BA / Sleeps 6

    38 Reviews

    $470

    Inquire

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

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

    Details

    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 …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (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!

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    $370

    3 BR / 2 BA / Sleeps 6

    42 Reviews

    $370

    Inquire

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

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

    Details

    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-…
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (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.

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    $450

    3 BR / 3 BA / Sleeps 6

    35 Reviews

    $450

    Inquire

    Villa Paradiso: A unique mid-town paradise

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

    Details

    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…
    • Internet Access
    • A/C or climate control
    • Patio
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (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 …

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    $173

    3 BR / 2 BA / Sleeps 6

    3 Reviews

    $173

    Inquire

    Elizabeth Retreat: A three bedroom historic home in Old Town

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

    Details

    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 …
    • Internet Access
    • A/C or climate control
    • Patio
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (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 …

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    $200

    3 BR / 3 BA / Sleeps 6

    1 / 19

    $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 …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $580

    3 BR / 3 BA / Sleeps 6

    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 …
    • Internet Access
    • A/C or climate control
    • Patio
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $540

    3 BR / 2 BA / Sleeps 6

    1 / 18

    $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 …
    • Internet Access
    • A/C or climate control
    • Patio
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $183

    3 BR / 3 BA / Sleeps 8

    1 Reviews

    $183

    Inquire

    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 …

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    $495

    3 BR / 4 BA / Sleeps 6

    7 Reviews

    $495

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    The Townhomes on Windsor - 3BR / 3BA

    Key West house
    3 BR / 4 BA / Sleeps 6 | Quick view
    Excellent7 Reviews

    Details

    Reviews

    (7)

    Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels. Each has it’s…
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (7)

    Awesome stay!

    Left on Mar 04, 2013 for a stay in November 2012

    We had a fabulous time here. The townhouse is just a couple blocks from Duval Street. We walked everywhere it was great. The house itself was beautiful and had everything we needed. This would be a great house to rent for a week as it has a washer and drier. We loved our stay and will definately rent again. Hopefully soon

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    $600

    3 BR / 3 BA / Sleeps 6

    10 Reviews

    $600

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    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.

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    $743

    3 BR / 4 BA / Sleeps 6

    1 / 22

    $743

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    The Water's Edge

    Key West house
    3 BR / 4 BA / Sleeps 6 | Quick view

    Details

    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable three-bedroom, four-bath lies …
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area

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    $575

    3 BR / 2 BA / Sleeps 8

    6 Reviews

    $575

    Inquire

    Abaco Dreams ~ Weekly Rental

    Key West house
    3 BR / 2 BA / Sleeps 8 | Quick view
    Average6 Reviews

    Details

    Reviews

    (6)

    Some wonderful changes are happening at the Abaco Dreams vacation rental. From the moment the new owners first stepped inside this beautifully maintained historic home, it was a love story about to unfold. With a passion for Key West wooden homes, they immediately began making furnishing upgrades, with an eye to the …
    • Internet Access
    • A/C or climate control
    • Linens Provided
    • Satellite or cable TV
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Nice house....bad letting agent!

    Left on Jan 03, 2012 for a stay in November 2011

    DON'T EXPECT THIS COMPANY TO REPLY TO YOUR CALLS ON ANY OF THEIR TELEPHONE NUMBERS! THEY DON'T PICK UP, NOT EVEN IN THE MIDDLE OF THE NIGHT WHEN THE ALARM SYSTEM IN THE HOUSE IS AT IT'S LOUDEST.

    Lovely Key West home, very traditional, as it looks in the brochure. Advertised to take 6, in our view only if 2 are small children. The lovely pool area is set for 4 .. chairs at the table, 4 …

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    $167

    3 BR / 2 BA / Sleeps 8

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    30 night minimum stay requirement. The Palms - 3 Bedroom House with a Swimmi

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

    Details

    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area is in between the …
    • Internet Access
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    • Microwave
    • Satellite or cable TV
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $183

    3 BR / 2 BA / Sleeps 6

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    $183

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    On Hemingway's Rounds ~ Monthly Rental

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

    Details

    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s …
    • Housekeeping Optional
    • A/C or climate control
    • Stereo or CD player
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $175

    3 BR / 2 BA / Sleeps 8

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    $175

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    Island Elegance ~ Near The Beach ~ Monthly Rental

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

    Details

    Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous…
    • Housekeeping Optional
    • A/C or climate control
    • Grill
    • Pet friendly - ask
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $200

    3 BR / 3 BA / Sleeps 7

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    $200

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    Luxurious Manor ~ Monthly Rental

    Key West house
    3 BR / 3 BA / Sleeps 7 | Quick view

    Details

    Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this Luxurious …
    • A/C or climate control
    • Parking
    • Satellite or cable TV
    • Stereo or CD player
    • Telephone
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $615

    3 BR / 3 BA / Sleeps 6

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    $615

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    Private Key West Sunset ~ Weekly Rental

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

    Details

    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island visitor should…
    • A/C or climate control
    • Balcony or terrace
    • Television
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    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $600

    3 BR / 3 BA / Sleeps 8

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    $600

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    Fantasy Resort Villa ~ Weekly Rental

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

    Details

    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in Old Town Key West. …
    • A/C or climate control
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    • Stereo or CD player
    • Smoking allowed - ask
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $400

    3 BR / 3 BA / Sleeps 6

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    $400

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    A Tropical Tradition (Gallup Arms) ~ Weekly Rental

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

    Details

    Nestled in one of Key West's original gated "mini-compounds," the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16…
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Linens Provided
    • Stereo or CD player
    • Telephone
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $250

    3 BR / 3 BA / Sleeps 8

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    $250

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    To The Nines ~ A Penthouse-Villa ~ Monthly Rental

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

    Details

    "Who says you can't have your cake and eat it too?" Well here's the proof you can ... and it's To the Nines -Key West vacation rental. When you rent this totally unique vacation rental, you will have the "best of both worlds" ... a penthouse and a pool courtyard villa, all wrapped up …
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $167

      3 BR / 3 BA / Sleeps 8

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      $167

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      30 night minimum stay requirement. Waterfront Escape - 3 Bedroom House on Ca

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

      Details

      Located in Big Coppitt is this secluded, waterfront paradise. This 3 bedroom, 3 bathroom house features a private pool. Relax in the grand outdoor patio area overlooking the pool and canal. Each of the three bedrooms has its own private bathroom. Located on the ground floor is the living room, dining area, kitchen and…
      • Internet Access
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      • Balcony or terrace
      • Linens Provided
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $175

      3 BR / 3 BA / Sleeps 6

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      $175

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      Mediterranean Caribbean Villa ~ Monthly Rental

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

      Details

      Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this "Casa el Paradiso" most …
      • Housekeeping Optional
      • A/C or climate control
      • Stereo or CD player
      • Telephone
      • Pet friendly - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $408

      3 BR / 2 BA / Sleeps 10

      3 Reviews

      $408

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      "TOON HALL @ TROPICAL VILLAGE" - Great For Large Groups. Close to ATL Ocean!

      Key West house
      3 BR / 2 BA / Sleeps 10 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the …
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
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      Details

      Reviews

      (3)

      Best vacation ever!

      Left on Jul 01, 2014 for a stay in June 2014

      We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable, perfectly situated blocks from the beach and Duvall Street. We were able to chill and grill at home by our pool or walk into town for a night of fun.We also loved the privacy and security the fenced yard offered.

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      $418

      3 BR / 4 BA / Sleeps 8

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      "ALEXANDRIA'S SECRET" Luxurious Home w/ Private Pool - 1/2 Block to Duval St

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

      Details

      Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost city has to offer- …
      • Internet Access
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      • Balcony or terrace
      • Grill
      • Linens Provided
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $508

      3 BR / 3 BA / Sleeps 10

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      $508

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      Conch Republic Cottages - 3 Bed 3 Bath Group Property - Steps from Duval St!

      Key West cottage
      3 BR / 3 BA / Sleeps 10 | Quick view

      Details

      This nightly group rental consists of 3 separate units. 1) Porchside Paradise 2) Orange Blossom Suite 3) Deckside Suite . Three separate bedrooms with queen sized beds. Two sleeper sofas and two private hot tubs! Located at 510 Petronia St, literally steps from Duval St! Take advantage of the vivid nightlife, …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • Deck
      • Grill
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $418

      3 BR / 4 BA / Sleeps 8

      50 Reviews

      $418

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      TROPICAL RETREAT- Upscale Home w/ Private Pool & BBQ Grill 1/2 Block To Duval

      Key West house
      3 BR / 4 BA / Sleeps 8 | Quick view
      Excellent50 Reviews

      Details

      Reviews

      (50)

      Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting nightlife, music, bars and …
      • Internet Access
      • A/C or climate control
      • Patio
      • Grill
      • Linens Provided
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (50)

      Perfect place to stay with a family

      Left on Jun 24, 2009 for a stay in July 2007

      It was truly a perfect place with the pool, patio, location, and was laid out just great. We had 8 people (4 adults & 4 teenagers) and had more than enuff room for everyone. Can't imagine anyone would be dissappointed. Also had a large enuff secure driveway that we could park our full size rental van inside behind a lockable gate (i.e. no parking problems).

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      $418

      3 BR / 3 BA / Sleeps 8

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      $418

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      ABSOLUTELY PARADISE - Luxury Home w/ Pvt Pool Just 1 Block To Duval St

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

      Details

      Absolutely Paradise! That's what you will think the moment that you arrive at this luxurious, tropical retreat. Located in the heart of Old Town Key West, this beautiful home will entice, entertain, and excite even the most discriminating traveler. This spacious (almost 2000 sq ft) three story, 3 bedroom, 2.5 bath …
      • Suitable for children - ask
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      • Wheelchair accessible - ask

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      $183

      3 BR / 3 BA / Sleeps 10

      1 / 24

      $183

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      "CAYO HUESO HIDEAWAY' - Luxury Monthly Rental - Pvt Pool & Pvt Hot Tub

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

      Details

      ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Cayo Hueso: As you approach the front door to 1120 Curry Lane the transformation starts to happen. The small lush tropical lane, the two wonderfully inviting porches... your journey to the tropics and relaxation has begun! …
      • Hot Tub/Jacuzzi
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Grill
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $408

      3 BR / 2 BA / Sleeps 6

      1 Reviews

      $408

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      COCONUT PALM - Bahama Village Home w/ Huge Pvt Hot Tub - Great for Families!

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

      Details

      Reviews

      (1)

      Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been transformed with bits and …
      • Internet Access
      • A/C or climate control
      • Ceiling Fans
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Absolutely perfect house for our group!

      Left on Jul 29, 2014 for a stay in July 2014

      This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management company was quick with checking in/out and very nice! We are making this an annual trip and will stay here again.

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      $338

      3 BR / 2 BA / Sleeps 8

      10 Reviews

      $338

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      "CASA KEY WEST @ DUVAL SQUARE" Extra Large Condo Located On Duval St.

      Key West condo
      3 BR / 2 BA / Sleeps 8 | Quick view
      Very Good10 Reviews

      Details

      Reviews

      (10)

      Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential units upstairs and …
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Linens Provided
      • Pet friendly
      • Suitable for children - ask
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      • Wheelchair accessible - ask

      Details

      Reviews

      (10)

      Beautiful Condo, Relaxing Community

      Left on Apr 02, 2013 for a stay in March 2013

      Had a great two-night stay with my all-adult family of 5. The condo has three full bedrooms so it was very comfortable for our group. The condo also features 2 completely windowed living areas (one upstairs, one downstairs) with stunning views of the harbor. The patio gets lots of sun for reading and sunbathing. We spent evenings cooking in the open kitchen and on the patio grilling.

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      $318

      3 BR / 2 BA / Sleeps 8

      9 Reviews

      $318

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      "AMELIA HOUSE" - Private Hot Tub - Half Block To Duval St - Sleeps 8!

      Key West house
      3 BR / 2 BA / Sleeps 8 | Quick view
      Excellent9 Reviews

      Details

      Reviews

      (9)

      Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which includes a kitchen …
      • Hot Tub/Jacuzzi
      • Internet Access
      • A/C or climate control
      • Deck
      • Grill
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (9)

      We didn't want to leave the amelia House!

      Left on Dec 02, 2013 for a stay in November 2013

      From the beginning, Craig in the office helped us find the right house for our vacationing family. He was a pleasure to work with! I am so glad we picked the amelia House. The location off Duval Street is the best. And a parking spot! Close to everything yet quiet for sleeping. It is so perfect for a group wanting 3 bedrooms. I expected a lot... but the house actually exceeded my expectations. …

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      $338

      3 BR / 2 BA / Sleeps 8

      45 Reviews

      $338

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      "HEMINGWAY'S VIEW" - Great Location, 3 BR 2 Bath, Decked Viranda and Hot Tub

      Key West house
      3 BR / 2 BA / Sleeps 8 | Quick view
      Excellent45 Reviews

      Details

      Reviews

      (45)

      One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks and large vanity …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • A/C or climate control
      • Patio
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (45)

      Great vacation home

      Left on Jun 25, 2009 for a stay in May 2009

      We stayed with a party of 5 and enjoyed the Hemingways view vacation home very much!
      The house is very well equipped and the backyard with the jacuzzi is perfect for relaxing after a day of sightseeing in Key West. Location is also perfect. Close to everything but quiet enough so you can have good night sleep. We would definately stay there again next time travelling to the keys.
      Arrangements for…

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      $408

      3 BR / 2 BA / Sleeps 6

      31 Reviews

      $408

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      "CASA SERENDIPITY" - World Class Comfort in Lush, Tropical Paradise

      Key West house
      3 BR / 2 BA / Sleeps 6 | Quick view
      Excellent31 Reviews

      Details

      Reviews

      (31)

      Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and one full bath …
      • Internet Access
      • A/C or climate control
      • Deck
      • Grill
      • Linens Provided
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (31)

      Very quaint

      Left on Jun 24, 2009 for a stay in March 2008

      Loved the house, nicely decorated and well kept. Lots of room except you
      need to watch your head going down the stairs - low clearance. Nice wrap
      around porch and yard with small pool (too cold for me but the kids loved it).
      The walk to town (Duval St area) was longer than expected especially since the
      house is across from the cemetary (above ground).

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      $133

      3 BR / 2 BA / Sleeps 6

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      $133

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      "SANDY BREEZE" 3 Bd 2 Bth Home w/ Private Pool

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

      Details

      ***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This newly renovated 3 bedroom "home away from home" sits right smack in the middle of the Key West island and is a short distance to everywhere you will want to go during your vacation! Located on Seminary St, in a quiet …
      • Internet Access
      • A/C or climate control
      • Grill
      • Linens Provided
      • Satellite or cable TV
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $408

      3 BR / 2 BA / Sleeps 10

      13 Reviews

      $408

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      "POOLSIDE PARADISE" Amazing Home 1/2 Block to Duval w/ Pool and Pvt Parking

      Key West house
      3 BR / 2 BA / Sleeps 10 | Quick view
      Excellent13 Reviews

      Details

      Reviews

      (13)

      POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living room. The bath with …
      • Internet Access
      • A/C or climate control
      • Deck
      • Grill
      • Linens Provided
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (13)

      Enjoyed our Stay

      Left on Oct 14, 2011 for a stay in September 2011

      The place was perfect for our group. My husband and I traveled with my parents and another couple. It worked out great because the parents stayed with us and our friends had their own little apartment which gave us all our privacy if needed. The location was pretty nice as well. We were one block off Duval. Even though we were down on the end closest to SouthernMost everything was within …

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