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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

Pete's Cottages

House
Bedrooms 4
2 Bathrooms

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall. 

Beach Club #103

Condo
Bedrooms 2
2 Bathrooms

Unique oceanfront living only 65 feet from the Atlantic!

The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water.  The breathtaking view can be seen as soon as you enter the unit.  

Southard Rooster Conch Suite - R

House
One Bedroom
One Bathroom
Rooster Conch is a one bedroom one bathroom suite in a house consisting of three vacation suites. Decorated with tropical color palette and has a queen bed. Accessed from the second floor covered porch that overlooks the shared gardens and pool below.

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 Calypso

House
One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Calypso is a peaceful retreat. Enter the home through the tranquil and inviting living space, accented with sage green walls, new tile floors and pops of color from local artwork and photography.

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 Penthouse

Condo
Bedrooms 4
4.5 Bathrooms

Freshly renovated in January 2019- and ready for you! 

Duval Square Penthouse has enough luxurious square footage for your whole crew to gather, relax, and make lasting memories together. 

Louisa House

House
Bedrooms 4
3.5 Bathrooms

An absolutely perfect location, just a half a block off Duval Street and within walking distance to amazing restaurants, turquoise beaches and the Southernmost Point in the United States. Louisa House has it all for the perfect Key West vacation.

Catherine House

House
Bedrooms 2
2 Bathrooms

This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.

Map View