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 25 - 36 of 67 rentals matching your search criteria
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Alluring Porches

Type

  • Townhouse
3 Bedrooms
3 Baths
6 Guests
Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you!

Duval Penthouse

Type

  • Home
3 Bedrooms
2.5 Baths
7 Guests
Location, location, location! Practically overlooking famous Duval Street from large upstairs deck!

Casa de Rosalie

3 Bedrooms
2 Baths
8 Guests
Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard.

Southard Square Hideaway

Type

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

Bahamian Reed

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again

2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West.

Coconut Cottage

Type

  • Cottage
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.

William's Loft

Type

  • Cottage
2 Bedrooms
1 Bath
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.

President's Walk

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch

Crowner's Jewel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!

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!

Key West Found

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Just steps away from Harry Truman's "Little White House" you find your dream come true spacious vacation rental home

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