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 86 rentals matching your search criteria
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Cayo Hueso Sunshine

Type

  • Home
2 Bedrooms
3 Baths
6 Guests
French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool.

Parrot Perch

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Unbeatable location! Only a block to famous Green Parrot bar yet in a secluded, quiet community of Truman Annex

Nautical Dreams

Type

  • Cottage
2 Bedrooms
2 Baths
6 Guests
In a small gated community this perfect cottage with a large private deck to allow all the privacy you would need to grill, dine and lounge.

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

Duval On The Square

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Rooftop community just steps away from Duval Street to great restaurants, shopping and entertainment.

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.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
8 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.

Mermaid's Dream

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home.

Boat House

1 Bedroom
2 Baths
2 Guests
This unique 1 bedroom, 2 bath cottage is about to become your home away from home!
Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE!

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.

Duval Penthouse

Type

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

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