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Key West Vacation Rentals

Book Key West’s Best Vacation Rentals

Rent Key West Vacations manages the best Key West Vacation Rentals. For over twenty years, we’ve connected with Key West property owners and represented many of Key West’s most historic homes. On this page, you'll find properties with private pools and ocean views. Each rental is unique, so you can easily discover the right place for your group. Browse Cottages, Beach Condos, and Historic Homes at the center of Old Town Key West.

Plan Your Dream Key West Vacation!

The following results matched your search criteria.

List View


One Bedroom
2 Bathrooms

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds: relaxing and taking advantage of all that Key West has to offer.

Bali Hideaway

Bedrooms 0.5
One Bathroom

Perfect for two, this Bali-style studio cottage has it all:  comfort, privacy and location.

Colony Poolside

One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork.

Duval Square Delight

Bedrooms 2
2.5 Bathrooms

28 Day Minimum Rental:  Duval Square Delight is located in a quaint town home community just steps from Duval Street. Upstairs there are residential units and a rooftop pool, while downstairs there are shops and restaurants surrounded by cobblestones and mature, tropical landscaping.

Ann Street Cottage

One Bedroom
1.5 Bathrooms

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.

Map View