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!

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Displaying 25 - 36 of 76 rentals matching your search criteria
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Conch Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals. A two-bedroom, two-bath condo, second floor condo in Truman Annex.

Pets Not AllowedWasher/DryerPoolGated Community
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Coral Breeze

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the perfect choice!

Pets AllowedWasher/DryerGrillPoolGated Community
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Newton's Nest

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
2 Guests

Newton's Nest is a quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence.

Pets Not AllowedWasher/DryerPool
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Shipyard Treasure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Finding a perfect property for your family vacation is easier said than done, but this contemporary condo at Truman Annex might just be the one.

Pets Not AllowedWasher/DryerPoolGated Community
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La Casita

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.

Pets Not AllowedWasher/DryerGrill
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Nautical Dreams

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.

Pets Not AllowedWasher/DryerGrillPool
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Atlantic Paradise

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.

ElevatorHot TubPets Not AllowedWasher/DryerGrillPool
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Tradewinds

Type

  • Condominium
Ocean Side
3 Bedrooms
2 Baths
6 Guests

A quick jaunt across the street takes you to Key West’s longest beach. A few blocks away you’ll discover dining and shopping galore on famous Duval Street. A short bike ride and you're at the Historic Seaport.

ElevatorHot TubPets Not AllowedWasher/DryerGrillPoolGated Community
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Tropical Dreaming

Type

  • House
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

Outdoor ShowerPets AllowedWasher/DryerGrillPool
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A Barefoot Retreat

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community. This two-bedroom, one bath, second floor condo will feel like your own tropical home the minute you walk through the door.

Pets Not AllowedWasher/DryerPoolGated Community
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Shrimp Party

Type

  • Townhouse
Old Town
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.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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