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 67 rentals matching your search criteria
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Bayview Harbor

Type

  • Condo
2 Bedrooms
1 Bath
5 Guests
Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West!

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.

Hidden Treasure

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space.

Shrimp Party

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

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

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!

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.

True Paradise

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Located in one of the most sought out neighborhoods "The Meadows" this lovely condo has everything you need to enjoy your time in Key West.

Duval Compound

Type

  • Home
6 Bedrooms
5.5 Baths
14 Guests
With an unbeatable location, two pools and all top of the line appliances Duval Compound is a true find among vacation rental properties

Key Lime Pie

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Private cottage that has all the amenities you would require for your stay, private pool, outdoor space for lounging, grill and dining. One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.

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