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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 65 results matching your search criteria
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Perfect Pineapple

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.

Windchime

0.5 Bedrooms
1 Bath
2 Guests
Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime!

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.

Osprey

Type

  • Cottage
0.5 Bedrooms
1 Bath
2 Guests
Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West has to offer!

Duval Breeze

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

Alluring Porches

Type

  • Townhouse
3 Bedrooms
3 Baths
6 Guests
Feel the tropical allure of this spacious home in the center-of-it-all community of the historic Truman Annex!

Easy Livin'

Type

  • Home
3 Bedrooms
4 Baths
8 Guests
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

The name says it all!

Beach House Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

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.

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.

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

The Dolphin House

Type

  • Home
4 Bedrooms
3.5 Baths
8 Guests
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.

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