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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Shipyard Treasure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Finding a perfect property for your family vacation is easier said than done, but this beautiful apartment might just be the one.

Contemporary Condo at Truman Annex - Walk to Beach/Duval Street

Captains Wheel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!

Emma's Escape

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

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

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!

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.

Conch Adventure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends

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!

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.

Duval Penthouse

Type

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

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.

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