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All of the rentals below have at least one available deal or discount, which can vary depending on when you book or when you plan to take your trip. Just click on the Explore All Specials button next to each listing to see the terms of the available deals. Searching your stay dates will show you all properties that have an available deal during that time. You can also view all of our current promotions and see the details of each one on our main Deals page.

Displaying 1 - 12 of 72 results matching your search criteria
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Ibis

Type

  • Cottage
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.

Treetop Paradise

2 Bedrooms
2 Baths
4 Guests
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Southard Square Hideaway

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.

Conch Wind

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!

Sundown Refuge

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Key West Charming

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!

Key West Casa

Type

  • Townhouse
3 Bedrooms
2 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.

Coral Breeze

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the logical choice!

Amelia Home

Type

  • Home
2 Bedrooms
2.5 Baths
6 Guests
After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home!

Lavender Jungle

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.

President's Walk

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind.

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