Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 1 bedroom cottages to large 5 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 61 - 72 of 72 rentals matching your search criteria
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A Place In Paradise

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Pets Not AllowedWasher/DryerPoolGated Community
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Flagler's Oasis

Type

  • House
Mid Town
2 Bedrooms
1 Bath
4 Guests

Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.

Pets AllowedWasher/DryerGrillPoolMonthly Rental
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Ibis

Type

  • Cottage
Old Town
1 Bedroom
1 Bath
2 Guests

Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home with a shared pool on property.

Pets AllowedGrillPoolGated CommunityMonthly Rental
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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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Boat House

Type

  • Cottage
Old Town
1 Bedroom
2 Baths
2 Guests

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

Pets Not AllowedWasher/DryerPoolMonthly Rental
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Breezy Bungalow

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
4 Guests

When a name says it all you know you have made the perfect choice for your Key West island escape.

Pets Not AllowedWasher/DryerPoolGated Community
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Coral Palm

Type

  • Townhouse
Stock Island
3 Bedrooms
3 Baths
6 Guests

Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock on Stock Island.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental
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Under The Palms

Type

  • House
Mid Town
2 Bedrooms
2 Baths
4 Guests

Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

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Conch Wind

Type

  • Townhouse
Old Town
2 Bedrooms
2 Baths
4 Guests

Stop searching, Conch Wind is the rental home in Key West you have been hunting for!

Pets Not AllowedWasher/DryerPoolGated Community
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Windchime

Type

  • Condominium
Old Town
0.5 Bedrooms
1 Bath
2 Guests

Searching for an affordable monthly vacation rental in the heart of Key West? Do you plan on spending most of your time enjoying all that Key West has to offer and seeing what if feels like to really live like a local? Then tune into Windchime!

Pets Not AllowedMonthly Rental
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Parrot Perch

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.

Pets Not AllowedWasher/DryerPoolGated Community
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