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Houses Key West

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58 houses

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 14 minutes

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$345

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 20 minutes

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$481

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 38 minutes

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$2,190

Seaside Place Key West FL 5 Bedroom House 4 Baths

Key West house

5 bedrooms / 4 bathrooms / sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

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$1,955

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 18 minutes

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$492

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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$328

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$340

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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$492

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

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$688

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms / 1 bathroom / sleeps 5

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$688

** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **

Key West house

1 bedroom / 1 bathroom / sleeps 4

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

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$281

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$517

Olivia Place

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

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$345

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

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$1,148

Old Town, 5 Bdrm Home with Private Pool in Gated Backyard

Key West house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 9 minutes

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$475

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms / 1 bathroom / sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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$103

A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20

Key West house

8 bedrooms / 8 bathrooms / sleeps 20

Responds fast! avg. 1 hour 44 minutes

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$2,028

Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$147

The Mermaids House, Historic Old Town Key West

Key West house

2 bedrooms / 1 bathroom / sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

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$287

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$259

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Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$487

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

4 bedrooms / 2 bathrooms / sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

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$1,722

Ocean View Estate with Private Pool 15 minutes from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

“Absolutely Perfect for Our Family of 11” We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we needed something, we could find it easily, or we called Cynthia---her help and knowledge is priceless! Kris stopped in twice to check on us, and we found him delightful. He knows so much history about the area! There is a large pool and a large play area with anything and everything you can imagine to play with, Since we had very young children with us, we were very happy with the lack of ocean access, as well as the locking gates to the pool area and the outside stairs. When we come back to the Keys, we will definitely stay at the White Ibis Inn!

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$487

Bahama House - A++ Location with private pool/parking - walk to everything!

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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$1,002

Ecco Domani Spacious, three story, private condo with private pool, downtown

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$202

FLAGLER'S OASIS Private Home, Lagoon Pool, Pet Friendly, Outdoor Living Space

Key West house

2 bedrooms / 1 bathroom / sleeps 4

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$184

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$179

The DOLPHIN HOUSE Spacious Home, Private Pool, BBQ, Great for Families

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

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$926

First Breath by AT HOME IN KEY WEST

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$202

Paradise Palms Traditional Conch House in Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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$116

ARTIST GARDEN Private Home, Patio + BBQ, Shared Pool, Family Fun, Quiet Lane

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$414

Private Pool with Atlantic Ocean View- 20 minutes away from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

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$601

LA CASITA Monthly Rental in the Heart of Old Town, Downtown Key West

Key West house

2 bedrooms / 1 bathroom / sleeps 4

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$153

TROPICAL DREAMING Private Home with Private Pool, Patio + BBQ, Pet Friendly!

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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$590

CASA GRANDE - Entertainers Dream, Great for Families and Events, Private Pool

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

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$1,506

AMELIA HOME Spacious Private Home with Private Pool, BBQ Grill + Pet Friendly

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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$587

Lighthouse Villa - Large, Tri-level Historic Conch Home with Private Pool

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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$309

UNDER THE PALMS with a Private Pool by At Home in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$184

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