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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

Duval Square Delight

Condo
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.

Albury Bungalow

House
Bedrooms 2
2 Bathrooms

28 Day Minimum Rental:  A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, one bathroom house also boasts a separate cottage bedroom with its own bathroom.

Villa Paradiso

House
Bedrooms 3
3 Bathrooms

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths.

Duval Square Retreat

Condo
Bedrooms 2
2.5 Bathrooms

Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.

Colony Poolside

House
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.

Elizabeth Retreat

House
Bedrooms 3
2 Bathrooms

28 Day Minimum rental:  Want to saunter through the historic streets of Key West and live like a local in a quiet, Old Town residential neighborhood? Look no further than Elizabeth Retreat.

Duval Square Courtyard Condo

Condo
Bedrooms 3
2 Bathrooms

In the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex.

Reynold's Retreat

House
Bedrooms 3
3 Bathrooms

28 Day Minimum rental:  Reynolds Retreat is quintessential Key West living.  Located just a few blocks off Duval Street, Reynolds Retreat is a delightful cottage filled with historic charm and modern convenience.

Map View