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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

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

Havana Lane

House
Bedrooms 2
2 Bathrooms

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends.

Townhomes on Windsor #6

House
Bedrooms 3
3.5 Bathrooms

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft.

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.

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 Sophistication

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  This restoration of a majestic Key West bungalow is simply incredible. Modernists will love this property. This two bedroom, two bath home has just been completely renovated.

Ann Street Cottage

House
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.

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.

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.

Heavenly Zen

House
Bedrooms 4
3.5 Bathrooms

Just a few blocks from Higgs Beach sits Heavenly Zen.

This four-bedroom home was recently renovated in February of 2019. Enter the home through the deep front porch— perfect for relaxing with a cocktail and chatting with the neighbors.

Map View