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Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$689

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Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$316

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$1,303

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$2,009

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.

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$329

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. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$344

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!!!!

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$134

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 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

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,124

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$1,491

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!!

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$2,065

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,147

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$345

Beautiful Home Located In Quiet neighborhood

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$340

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$268

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$493

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 8 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$481

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$259

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$482

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

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$166

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

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$378

Sweet Caroline Seaport Floor 2

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$276

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$345

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,337

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$614

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,147

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$431

Sweet Caroline Seaport Key West Home Rental

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$314

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$859

“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!~

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$796

Lighthouse Suites Collection Duval St. and Pool

Key West house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,863

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$153

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$138

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$93

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$179

Great rentals within 20 miles that match your search

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$976

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