Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 37 - 48 of 63 rentals matching your search criteria
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Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
A beautifully designed yet comfortable private home that you may never want to leave, only to go outside to your private pool and secluded space to hang out - that's the Verandah!

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!

Tropical Dreaming

Type

  • Home
2 Bedrooms
2.5 Baths
6 Guests
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido!

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!

Bahamian Reed

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

A Barefoot Retreat

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Looking for the perfect home away from home? No need to look any further!

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community.

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.

Linger Longer

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation!

Parrot Perch

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.

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.

Duval Sea Turtle

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything!

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