Key West Vacation Rentals

You are here

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!

Displaying 1 - 12 of 66 rentals matching your search criteria
Map View
List View

Lighthouse Villa

Type

  • House
Old Town
3 Bedrooms
4.5 Baths
8 Guests

Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

The Dolphin House

Type

  • House
Old Town
4 Bedrooms
3.5 Baths
8 Guests

Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.

Papaya Place

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

This great 2 bedroom, 2 bathroom, Key West condo located at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve.

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.

Paradise Place

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

Lavender Jungle

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.

Cottage by the Pool

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

In this cozy home you will find yourself nestled in the center of the Key West Golf Club on a secluded lane that cuts through the heart of its community.

Brisa Del Mar

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Enjoy spectacular ocean views from this lovely rental!

Beach House Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

Wind Swept

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
6 Guests

Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. All that and much more awaits you at Windswept!

Duval Sea Turtle

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle town home within easy walking distance to everything!

Coral Garden

Type

  • Townhouse
Stock Island
2 Bedrooms
2.5 Baths
4 Guests

Coral Garden is a two bedroom town home in the quiet gated community of Coral Hammock located on Stock Island. Perfect for families or those who are working from home. Close to all that Key West has to offer.

Pages