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Houses Key West

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46 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 56 minutes

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$300

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

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Price per night from

$480

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

Responds fast! avg. 3 hours 42 minutes

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$2,119

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 11 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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$430

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$339

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$1,144

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms / 1 bathroom / sleeps 5

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$1,144

** 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!~

Responds fast! avg. 2 hours 58 minutes

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$446

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$516

Olivia Place

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

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$344

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

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$1,488

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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$133

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$144

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.

Responds fast! avg. 1 hour 9 minutes

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$328

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

2 bedrooms / 1 bathroom / sleeps 6

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$258

Poolside Home, Salty ocean breezes, Morning Sunrises, 15 Minutes to Downtown.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

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$716

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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Price per night from

$2,060

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!

Responds fast! avg. 2 hours 59 minutes

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$544

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$179

Sweet Caroline Seaport Key West Home Rental

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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$208

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$313

Key West House

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$687

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$184

Sweet Caroline Seaport Floor 2

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$189

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

2 bedrooms / 1 bathroom / sleeps 5

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$184

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$174

LOTUS BLOSSOM - Updated 3 BR Home With Tropical Courtyard & Hot Tub, Convenient

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$93

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$264

Great rentals within 20 miles that match your search

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$175

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$233

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$177

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$172

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 10

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$384

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 8

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$332

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$4,008

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 6 minutes

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Price per night from

$423

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

4 bedrooms / 3 bathrooms / sleeps 11

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Price per night from

$896

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