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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

Louisa's Hideaway

House
Bedrooms 3
3 Bathrooms

Tucked away near the quite end of Duval Street, you'll find this stylish, newly renovated, three bedroom, three bath home.  Thoughtful details are luxuriously appointed to appeal to the traveler looking for privacy, style and elegant design.

Beach Club #408

Condo
Bedrooms 4
3 Bathrooms

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths.

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.

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.

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.

Eliza's Jewel

House
Bedrooms 3
3 Bathrooms

28 Day Minimum rental:  Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West.  Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved hist

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.

Canalfront Cottage

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental:  Away from the hustle and bustle of Old Town, behind the coral-topped privacy fence, lies this stunning, secluded apartment overlooking the Riviera canal.

Southard Rooster Conch Suite

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.

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.

Map View