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$150

3 BR / 2 BA / Sleeps 8

30 night minimum stay requirement.  Manatee Manor - Summerland Key vacation rentals
1 / 8

$150

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30 night minimum stay requirement. Manatee Manor

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then cook some of the catch out on your deck with a few cold ones. And while…
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$117

2 BR / 2 BA / Sleeps 6

Amazing Grace - Summerland Key vacation rentals
1 / 17

$117

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Amazing Grace

2 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Amazing Grace is nestled in the middle of the island on Seidenberg Avenue that dead ends into Salt Run Canal that divides Key West in half. With 2 bedrooms, 2 bathrooms, off street parking and a hot tub you may find that you …
  • Dishwasher
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

4 BR / 3 BA / Sleeps 10

30 night minimum stay requirement.  Key Haven Retreat - 4 Bedroom House with - Summerland Key vacation rentals
1 / 31

$167

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30 night minimum stay requirement. Key Haven Retreat - 4 Bedroom House with

4 BR / 3 BA / Sleeps 10 | Quick view

Details

This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar area where you can …
  • 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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$260

2 BR / 3 BA / Sleeps 4

1 / 28

$260

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"THE FOREVER AFTER HOUSE" KW Golf Club Home on 18th Fairway w/ Pvt Pool, Spa

2 BR / 3 BA / Sleeps 4 | Quick view

Details

Luxury living on the 18th tee! Arguably the most beautiful home on the Key West golf course, meticulously created by Key West's premier interior designer. The best location to enjoy the peace and quiet with your special friends and family. BBQ on your spacious deck by the private pool. Ready access to the Key West…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$213

2 BR / 2 BA / Sleeps 6

1 Reviews

$213

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VO-093

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

180 degree wrap around porch with patio furniture. 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. Panoramic view from front room with three sets of glass sliders. TV, DVD player, queen sleeper sofa. Kitchen island, side by side refrigerator with water dispenser. Master …
  • Internet Access
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fabulous ocean views

Left on Mar 07, 2013 for a stay in February 2013

We absolutely loved every minute of our stay in Venture Out#93. The house was very clean and decorated in a wonderful tropical décor. We didn't want for anything...if anything, it was better than thought it would be. Being right on the water was spectacular, especially in the morning with the sunrise. We did not want to leave. Hard to complain about anything, but we were wondering where the …

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$186

3 BR / 2 BA / Sleeps 8

BRAND NEW 3 bedroom, 2 bath with dockage and great introductory pricing!!!!!! - Summerland Key vacation rentals
1 / 36

$186

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BRAND NEW 3 bedroom, 2 bath with dockage and great introductory pricing!!!!!!

3 BR / 2 BA / Sleeps 8 | Quick view

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A paradise is immersed when entering Ramrod Key. It offers you a close relationship with the nature displaying an exuberant vegetation bordering the sea water canals. Ramrod Key is known as Breezeswept because of the breezes that sweep it through. This is a well located house, walking distance to a Looe Key Tiki Bar…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$171

2 BR / 0 BA / Sleeps 6

1 / 21

$171

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WI-27321

2 BR / Sleeps 6 | Quick view

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Brand new home with high end features just two canals from open water. Large seawall with dock posts, fish cleaning table and swim ladder. Upstairs relax or dine on huge screened deck overlooking canal with dining furniture and two lounge chairs. Two sets of double glass sliders lead into main inside area. Living …
  • Internet Access
  • Dishwasher
  • Microwave
  • Satellite or cable TV
  • Ceiling Fans
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$329

2 BR / 2 BA / Sleeps 6

6 Reviews

$329

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Tropical Paradise Oceanfront Home with Pool

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of bed. This home …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(6)

Truly is a Tropical Paradise!!!

Left on Nov 23, 2011 for a stay in November 2011

We spent an idyllic week at Walkabout Retreats' Tropical Paradise 12-19 Nov. The house is beautifully and comfortably decorated, and extremely well appointed - everything we needed to cook up awesome seafood was provided, there was a notebook full of information about local restaurants and attractions, and wireless internet allowed us to keep up with weather and sea conditions for boating. The …

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$133

2 BR / 2 BA / Sleeps 6

1 / 14

$133

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30 night minimum stay requirement. 2 Bedroom 2 Bathroom Condo with Beautiful

2 BR / 2 BA / Sleeps 6 | Quick view

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30- Night minimum stay: Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Beautifully decorated with palm tree décor, leather sleeper sofa, warm colors to give …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

3 BR / 3 BA / Sleeps 8

1 / 19

$167

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

3 BR / 3 BA / Sleeps 8 | Quick view

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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
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$275

2 BR / 2 BA / Sleeps 6

1 / 15

$275

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Keys Waterfront Vista

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Waterfront 2 bedroom stilt home with 2 full baths with tubs, large great room, fully stocked kitchen, cable, wifi, interenet, washer/ dryer, central a/c. `house is located on a clean, swimmable deepwater flow through canal with a 60 ft cement dock. Ladder for easy exit. Property large enough to handle a boat and …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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CAT ISLAND SUITE #205 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

2 BR / 2 BA / Sleeps 6 | Quick view
“ Terrible ” 1 Reviews

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Aweful

Left on Nov 11, 2014 for a stay in October 2014

Avoid this place at all costs . It is horrible ….. I would rather have stayed in my car. The apartment was disgusting . Furniture looked like it was from the early 80's and was dirty.

The walls are mirrored and broken, fixed with tape. The smoke alarms are missing but the wires are hanging out of the walls. I would never stay there again. I do have to say the girl at the front desk was nice …

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$200

3 BR / 3 BA / Sleeps 6

8 Reviews

$200

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Reel Paradise - Big Pine Key

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large screen plasma TV in …
  • Waterfront
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(8)

Comfort & Privacy at Reel Paradise

Left on Jul 29, 2013 for a stay in September 2012

Reel Paradise was the perfect place for our Keys trip last year. We completely loved the layout of this house and the comfort and luxury it provided. The entire interior of the house is covered in cedar planks including the interior of the roof. The furniture is all Tommy Bahama and the kitchen has a nice big island to prep and serve all the food we made each night.

The canal system is …

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$500

4 BR / 3 BA / Sleeps 8

5 Reviews

$500

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Ocean Front-Heated Pool-View Over The Atlantic

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

Unwind and take a deep breath, you have finally found your tropical paradise vacation home. This 4 vacation home is the perfect getaway from the hustle and bustle of everyday life. Only 20 minutes from Key West! If you are ready to kick off your shoes and sit by the pool or grab that fishing pole and hop the next boat…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(5)

What a clean, relaxing and fun place to stay!

Left on Jun 06, 2013 for a stay in May 2013

The house was much bigger than it looked on the site. The pool was able to be heated and we loved being in it all hours of the day or night. Other than the food we needed for the week this house had everything! We used the kayaks provided and really enjoyed the wildlife and nature in the area. Can't wait to rent it again for next years vacation!

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$171

2 BR / 2 BA / Sleeps 4

1 / 11

$171

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VO-198

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Wrap around open water view with a huge 61' concrete dock/seawall, complete with cleats, padded aluminum dock posts,mooring whip holders,and hose. Covered deck with lounge furniture to dine out or enjoy an evening drink. Or eat inside on upscale dining set and still enjoy the million dollar ocean view. Kitchen is…
  • Internet Access
  • Grill
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$118

2 BR / 1 BA / Sleeps 6

1 Reviews

$118

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VO-116

2 BR / 1 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Freshly redecorated canal front home. Living room has a 32' flat screen TV with DVD, two sleeper sofas . Master bedroom has full size bed, mirror closet and a vanity with drawers. Guest bedroom has twin trundel bed with mirror closet and slider doors to patio and canal. Spacious open kitchen area with many …
  • Internet Access
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Nice queit place to stay

Left on Nov 23, 2013 for a stay in October 2013

Two bedrooms, living room, full kitchen and bathroom was enough to accommodate five people. Place is quiet, but not very close to public beaches. For the end of October there are many vacant units, so it looks really peaceful. Good resting area on backyard. Internet is not provided, cell phone connection and Internet on phone are poor at house but well enough outside.

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$85

1 BR / 1 BA / Sleeps 2

6 Reviews

$85

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Tropical Garden Guest House (sleeps up to 3)

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

Want to visit the Florida Keys without the high price tag of Key West? Here is a great option for you. We have a tropical hidden guest house on our property in Big Pine Key to provide the perfect relaxing vacation that you need. *Please read below the disclaimer to understand you will be living in a trailer…
  • Internet Access
  • A/C or climate control
  • Parking
  • Books
  • Garden
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(6)

Just perfect!

Left on Dec 03, 2013 for a stay in November 2013

This beautiful small place in paradise was so nice. It was perfect for two of us. The place was so clean, just spotless. Lane was so helpful with all questions and needs.

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$121

2 BR / 2 BA / Sleeps 6

1 Reviews

$121

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VO-438

2 BR / 2 BA / Sleeps 6 | Quick view
“ Terrible ” 1 Reviews

Details

Reviews

(1)

Canal front home with spacious ambiance. 35’ seawall with dock posts, cleats, fish cleaning table with hose and outdoor shower. Covered back deck with ceiling fan, drop shades and patio furniture. Living room has large Flat Screen TV with DVD, sleeper sofa, two rockers, recliner and door to covered deck. Master …
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Dirty!

    Left on Sep 18, 2014 for a stay in September 2014

    Upon entering the house, floors were dirty. Cabinets had roach feces all through out and live roaches in the oven drawer and in cabinets. Did not cook food in the home the last few days because the roaches were coming out. Carpets and Lazy boy chairs were stained. Put towels on chairs as a barrier so we could sit on them. Washed all linens and towels prior to use. Washed floors, counter tops, …

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    $107

    2 BR / 2 BA / Sleeps 6

    1 / 8

    $107

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    Waterfront 2/2 with 35' Dock in the Lower Keys

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two bathrooms, central air…
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly - ask

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    $100

    3 BR / 2 BA / Sleeps 6

    1 / 19

    $100

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    Charming 3bedroom/2bath home in the Florida Keys

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and snorkeling has never …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask

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    $100

    1 BR / 1 BA / Sleeps 4

    1 / 9

    $100

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    VO-122

    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    This clean and very well maintained canal front vaction home features 1Bd/1Ba with master bedroom king size bed with access to the full size bathroom. Living room features a futon sleeper with 32' flat screen television with DVD player. 35'concrete seawall features dock posts, cleats, swim ladder.ships.concrete …
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $171

      2 BR / 2 BA / Sleeps 6

      1 / 11

      $171

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      VO-194

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Just three lots in from the open water!! Newly renovated and sophisticatedly decorated vacation home has an ocean view from 35’ concrete seawall. Dock has posts and cleats for mooring your boat also lounge furniture and mosaic picnic table for relaxing and dining al fresco. Living room with canal view has flat …
      • Internet Access
      • Satellite or cable TV
      • Ceiling Fans
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $150

      4 BR / 3 BA / Sleeps 8

      1 Reviews

      $150

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      "SEABREEZE" Monthly Rental -Sanctuary- Golf Course

      4 BR / 3 BA / Sleeps 8 | Quick view
      “ Very Good ” 1 Reviews

      Details

      Reviews

      (1)

      28 NIGHT MINIMUM STAY REQUIREMENT - SEABREEZE 4 Bedroom 3 Bath with Off Street Parking, Private Heated Pool, Fitness Center, Gorgeous!! A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the "Sanctuary" on the Key West …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (1)

      Awesome Month!!!

      Left on May 01, 2014 for a stay in February 2014

      We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the pool. [the pool company not sweeping the pool} a lot of vegetation so many leaves and such in pool. Gym [we were told it was included and they tried charging us, took a few days to get key] But, I will say everything worked …

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      $100

      2 BR / 1 BA / Sleeps 6

      1 / 10

      $100

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      VO-313

      2 BR / 1 BA / Sleeps 6 | Quick view

      Details

      Affordable vacation home beautifully decorated in peaceful pastel colors. This home has many nice features including being bright, spacious and tropically decorated. The living room area has a Flat screenTV with DVD & VCR, queen size sleeper sofa, glass top table and comfy chairs. Master bedroom has a queen size bed…
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $136

      2 BR / 2 BA / Sleeps 6

      1 Reviews

      $136

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      VO-392

      2 BR / 2 BA / Sleeps 6 | Quick view
      “ Excellent ” 1 Reviews

      Details

      Reviews

      (1)

      Relax enjoying water views from both front and back decks. This home was recently redecorated with comfy upscale furniture and art. Large open living room has flat screen TV with DVD. Furniture is microfabric sleeper sofa, love seat and an armchair with hassock. Kitchen is conveniently laid out with a side by …
      • Internet Access
      • Dishwasher
      • Microwave
      • Satellite or cable TV
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      This clean and inviting house is nicer than I had imagined.

      Left on Nov 10, 2014 for a stay in November 2014

      We had a wonderful stay at Venture Out. It was very peaceful and enjoyable. The internet was fast and the cable TV had plenty of channels. The appliances and furniture are modern and well cared for.

      We are hoping to return soon.

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      $100

      1 BR / 1 BA / Sleeps 4

      1 Reviews

      $100

      Inquire

      VO-608

      1 BR / 1 BA / Sleeps 4 | Quick view
      “ Very Good ” 1 Reviews

      Details

      Reviews

      (1)

      38' seawall with dock posts, cleats, fish cleaning table and swim ladder. This home has a large covered, screened porch with upscale patio furniture including a large table with four comfortable chairs, a swinging love seat and several swivel chairs. The master bedroom has a queen size bed with mirror closet and …
      • Grill
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Very nice place

      Left on Apr 23, 2014 for a stay in April 2014

      The unit was nice and clean. Everything worked good. The screen porch was very popular.. I did not have a chance to have my boat there but the dock area was in good shape. The only thing the owners should do is get some better sleep sofa's. The one we used was uncomfortable.

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      $114

      2 BR / 2 BA / Sleeps 6

      1 / 9

      $114

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      VO-529

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Check-out this vacation home! It is situated on the widest canal in Venture Out!! Located on a 35' concrete dock with cleats and dock posts. Beautiful views of the open water from the living room, dining area and kitchen. Recently remodeled, clean fresh decor. Living room has a 26' flat screen TV and queen size …
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $186

      2 BR / 2 BA / Sleeps 6

      1 Reviews

      $186

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      VO-218

      2 BR / 2 BA / Sleeps 6 | Quick view
      “ Very Good ” 1 Reviews

      Details

      Reviews

      (1)

      Panoramic open water view! Enjoy this hypnotic view from living room, dining area and kitchen. Unusually large 50' seawall with cleats, swim ladder and fish cleaning table. Flat screen TV with DVD conveniently placed for viewing from living room, dining area and kitchen. Living area has comfortable queen size …
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Comfortable with a gorgeous view!

      Left on Oct 27, 2014 for a stay in August 2014

      Enjoyed our stay. Lots to see and do! The view was breathtaking and the resort was in a great location. The pools and hot tub were very convenient. We would definitely visit again!

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      $210

      2 BR / 2 BA / Sleeps 6

      1 Reviews

      $210

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      Penthouse Condo in Key West Florida

      2 BR / 2 BA / Sleeps 6 | Quick view
      “ Average ” 1 Reviews

      Details

      Reviews

      (1)

      Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the beautiful pool and …
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Parking
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (1)

      Noisy inconsiderate poorly behave guests

      Left on Sep 03, 2013 for a stay in September 2013

      Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day they were all over the pool and parking and once again kept me up until 4:29 PM. By Sunday I was a wreck, very tired and could not stop yawning with a severe headache and not for having a hang over but from lack of …

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      $350

      3 BR / 2 BA / Sleeps 8

      12 Reviews

      $350

      Inquire

      Key West - Libra

      3 BR / 2 BA / Sleeps 8 | Quick view
      “ Excellent ” 12 Reviews

      Details

      Reviews

      (12)

      Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of "members only" amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and much more! This …
      • Waterfront
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • A/C or climate control
      • Balcony or terrace
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (12)

      Fantastic time

      Left on Mar 28, 2013 for a stay in October 2012

      We all had a great time. It was far away from everything yet close to everything at the same time. Restaurant had excellent food and pool was great. On the downside the boat was not cleaned when we got there and the hammock I so looked forward to was not there. All n all it was a great time n we rented it again this year. Hope it's clean n ready this year when we get there

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      $114

      2 BR / 2 BA / Sleeps 6

      1 / 7

      $114

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      VO-417

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Newly renovated canal front home. 35’ seawall with dock posts and swim ladder. Glass sliders to Florida room with view of canal, flat screen TV, sofa and beautiful dark wood furniture. Living room also with glass sliders to off street parking has a flat screen TV in decorator wood armoire, sleeper sofa and table. …
      • Internet Access
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $107

      1 BR / 1 BA / Sleeps 4

      2 Reviews

      $107

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      VO-513

      1 BR / 1 BA / Sleeps 4 | Quick view
      “ Very Good ” 2 Reviews

      Details

      Reviews

      (2)

      Enjoy fabulous canal and open water views from the dining room, living room, and covered deck. 35‘ dock with cleats, dock posts, swim ladder and picnic table. Florida living room has TV with DVD & VCR, two queen sleeper sofas, two wicker chairs and love seat. Dining area with wood dining table is bright and …
      • Grill
      • Satellite or cable TV
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (2)

      Really Lovely place…BUT “ADD-ON FEES” WILL KILL YOU…!!!

      Left on Nov 15, 2013 for a stay in November 2013

      I really liked the Ventue Out Experience, Nice clean, quaint, charming, Island Condo Style unit…Located in an VERY upscale RV park, on the water… 30 mins to Key West..

      …ONE BAD THING WAS “ADD-ON FEES”…

      Price for Room on the internet shows $107 per night…

      But you have… Cleaning fee $95, Processing fee $30, Taxes $45, Security fee $45, PLUS A CHECK-IN FEE OF $53.75 (pay in cash …

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      $86

      1 BR / 1 BA / Sleeps 4

      1 / 7

      $86

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      VO-003

      1 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Private backyard with dining/lounging furniture. Bright open Florida room with TV and two sleeper sofas. Attractive dining area with glass and white wood table. Kitchen conveniently arranged with appliances. Bedroom with full size bed. With this rental enjoy all the Venture Out amenities - pool, hot tub, tennis, bocce…
      • Grill
      • Satellite or cable TV
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $350

      3 BR / 2 BA / Sleeps 8

      12 Reviews

      $350

      Inquire

      Key West - MV Coconuts

      3 BR / 2 BA / Sleeps 8 | Quick view
      “ Excellent ” 12 Reviews

      Details

      Reviews

      (12)

      The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over 1100 sq ft of indoor …
      • Waterfront
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • A/C or climate control
      • Balcony or terrace
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (12)

      awesome stay in Key West

      Left on Apr 04, 2013 for a stay in September 2012

      Great large space to share with friends, yet you all have privacy with multiple floors and decks. The beds could use some new mattresses and sheets, but otherwise it was much better than a b & b. The marina is just outside of town and provides a safe quiet stay. The club house has great food and services. During our stay, our a/C went out and our host worked into the wee hours of the morning …

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      $157

      2 BR / 2 BA / Sleeps 6

      1 Reviews

      $157

      Inquire

      VO-279

      2 BR / 2 BA / Sleeps 6 | Quick view
      “ Very Good ” 1 Reviews

      Details

      Reviews

      (1)

      You will fall in love with the happy colorful tropical decorations in this canal front home. 35' seawall with whips, high end dock posts, cleats, swim ladder. Large table, comfortable patio chairs and lounging furniture to enjoy the seawall view and shade under the home. Upper deck has a view of canal, table and …
      • Grill
      • Satellite or cable TV
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Nice property on a friendly resort

      Left on Jan 03, 2015 for a stay in December 2014

      Nice property on a friendly resort. Goods and bad points:-

      Small shop with a simple selection of key essentials

      Onsite parking underneath the property

      Plenty of storage

      No Wi-Fi in the property and we had problems connecting in the hall, some other guests were having the same problem

      Fault with the smoke detector went off all night long

      Queen beds.

      No hairdryer or cleaning liquids …

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      $467

      5 BR / 5 BA / Sleeps 14

      1 / 40

      $467

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      "SHARK KEY CHATEAU" Incredible 3-Story Mansion w/ Private Beach, Pool, & Spa

      5 BR / 5 BA / Sleeps 14 | Quick view

      Details

      ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is designed in true keys …
      • Private Beach
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $220

      2 BR / 1 BA / Sleeps 4

      7 Reviews

      $220

      Book

      Sail Florida Adventures | Days and Sunset sails

      2 BR / 1 BA / Sleeps 4 | Quick view
      “ Excellent ” 7 Reviews

      Details

      Reviews

      (7)

      What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet. Fully functional …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • A/C or climate control
      • Suitable for children - ask

      Details

      Reviews

      (7)

      Very Relaxing

      Left on Feb 23, 2014 for a stay in February 2014

      The boat is exactly as stated and I found the accommodations very pleasant and comfortable . We stayed three nights. However some people might not as there are very "tight quarters" on relatively small boats. And I would not recommend it to individuals with mobility issues. The marina is very safe and the clubhouse and pool very nice. Our host was very nice and met us at the boat and …

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      $129

      2 BR / 2 BA / Sleeps 4

      1 / 7

      $129

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      VO-085

      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      This charming two bedroom, two bath home has been totally renovated and updated for your comfort and enjoyment! Spacious, open floor plan in the living room/dining room/kitchen area is excellent for entertaining!! Nice covered patio area - perfect for relaxing or reading your favorite book. 35' concrete dock/…
      • Grill
      • Microwave
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $493

      6 BR / 4 BA / Sleeps 12

      6 Reviews

      $493

      Inquire

      Family Retreat Oceanfront Home with Pool

      6 BR / 4 BA / Sleeps 12 | Quick view
      “ Excellent ” 6 Reviews

      Details

      Reviews

      (6)

      Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. Floating dock is great to fish and swim off of and it will …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Washing Machine
      • Pet friendly
      • Smoking allowed - ask
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (6)

      Can Book Correctly

      Left on Jun 21, 2011 for a stay in March 2011

      I am very disappointed. I had the families all sold on this place and ready to go. Now I need to phone and say the dates you said were available are not as you didn't look at the dates.

      Sorry, but I am not impressed.

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      $83

      2 BR / 2 BA / Sleeps 6

      1 / 29

      $83

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      "SEASIDE HIDEAWAY" Beautiful Key West Condo w/ Shared Pool & Tennis Courts

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      ***Due to licensing restrictions, this property requires minimum stay of 28 nights*** This condominium is located right near the entrance of Key West and offers unparalleled seclusion and privacy. Although it is on the opposite side of the island from world famous Duval St, it is only about a 10 minute drive away. …
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $110

      2 BR / 1 BA / Sleeps 4

      1 / 13

      $110

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      VO-536

      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Two bedroom home with ocean view from living room and deck. Living room has a queen size sleeper sofa, flat screen TV.Smart TV with Wifi for your devices. Kitchen is open and inviting with wood tone cabinets. Dining area located in a pleasant alcove near kitchen has a glass top table with seating for four. Master …
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $200

      3 BR / 3 BA / Sleeps 7

      1 / 16

      $200

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      Luxurious Manor ~ Monthly Rental

      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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      $83

      2 BR / 2 BA / Sleeps 6

      1 / 24

      $83

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      "SALT POND HIDEAWAY" 2/2 Condo w/ Huge Shared Pool & Hot Tub. Close to Beach!

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • A/C or climate control
      • Deck
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $139

      2 BR / 2 BA / Sleeps 6

      4 Reviews

      $139

      Book

      Captain Ron's Keys Caribbean Retreat

      2 BR / 2 BA / Sleeps 6 | Quick view
      “ Excellent ” 4 Reviews

      Details

      Reviews

      (4)

      This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of concrete seawall with bumpers to protect boat …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (4)

      Great place to stay and relax

      Left on May 19, 2013 for a stay in May 2013

      Loved this place very clean and peaceful would definitely go back!!! The key deer were amazing, came right into the yard, so cute. Canal right behind the house perfect to have a boat. It feels out of the way but it is still close enough to attractions the keys have to offer.

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      $215

      2 BR / 2 BA / Sleeps 6

      1 / 4

      $215

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      Key West Hyatt Windward Pointe

      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
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Smoking allowed - ask
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

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      $250

      2 BR / 2 BA / Sleeps 6

      1 / 17

      $250

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      Sunrise Suites Resort

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling, parasailing, or just …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $121

      2 BR / 1 BA / Sleeps 4

      1 / 8

      $121

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      VO-309 DO NOT RENT FOR LOBSTER

      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Cute as can be! Tastefully decorated with cozy comfortable furniture. Close to all of the amenities, including the pool, community store, marina, recreation hall, bocce ball courts, etc. Queen bed in one room and a double bed in the second bedroom Nice, large deck on front of home with table and chairs and water …
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $129

        2 BR / 2 BA / Sleeps 4

        6 Reviews

        $129

        Book

        A tropical paradise in the florida keys

        2 BR / 2 BA / Sleeps 4 | Quick view
        “ Excellent ” 6 Reviews

        Details

        Reviews

        (6)

        This is a very cute 24x32 two bedroom, two bathroom home located on mile marker 23 just 19 miles from the entrance to key west. The house has a very nice fully equipped kitchen. All the floors are tile with the exception of the master bedroom which is bamboo. The master bedroom comes with its own bathroom, queen size …
        • Waterfront
        • Ocean or water views
        • Hot Tub/Jacuzzi
        • Housekeeping Optional
        • Washing Machine
        • Suitable for children - ask
        • Suitable for the elderly - ask

        Details

        Reviews

        (6)

        Cute Place surrounded by beauty!

        Left on Apr 19, 2012 for a stay in April 2012

        The house was wondefully decorated and clean. The ammenities was a hit with my 5 year old. He loved the pool and playing boccie ball and shuffle board. It is close to some really good restaurant. It was nice to sit on the back dock and relax and look at the beautiful view. The house worked really well for us with the 2 bed rooms and bath rooms everyone had there own privacy.
        Had a Great time …

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        $300

        2 BR / 3 BA / Sleeps 6

        1 / 11

        $300

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        Island Brownstone ~ Weekly Rental

        2 BR / 3 BA / Sleeps 6 | Quick view

        Details

        An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as "Truman Annex", this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean reinterpretation. …
        • A/C or climate control
        • Porch
        • Grill
        • Television
        • Stereo or CD player
        • Suitable for children - ask
        • Suitable for the elderly - ask
        • Wheelchair accessible - ask

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        $198

        2 BR / 2 BA / Sleeps 6

        1 / 25

        $198

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        SAINT MARTIN SUITE #207 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

        2 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
        • Shared outdoor pool (unheated)
        • Hot Tub/Jacuzzi
        • Internet Access
        • A/C or climate control
        • Balcony or terrace
        • Pet friendly
        • Suitable for children - ask
        • Suitable for the elderly - ask
        • Wheelchair accessible - ask
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