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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

Sanctuary on Simonton

Condo
Bedrooms 2.5
3 Bathrooms

28 DAY MINIMUM- Dogs allowed, with restrictions

Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway.

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.

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.

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.

Colorscape

Condo
One Bedroom
One Bathroom

28 Day Minimum Rental: Colorscape is a spacious one bedroom condo in a four apartment complex in the Casa Marina District of Key West, close to the Atlantic Ocean, but still just a few blocks from Duval Street.

Villa Serena @ Duval Square

Condo
Bedrooms 2
2.5 Bathrooms

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary.  Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.

La Brisa #403E Ocean Vista

Condo
Bedrooms 2
2 Bathrooms

La Brisa Beach Condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation.

Duval Square Castaway

Condo
Bedrooms 2
2.5 Bathrooms

This condominium is located in the heart of Old Town and is convenient to just about everything! 

Dreaming on Duval

House
Bedrooms 5
4 Bathrooms

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval!

Southard Street - Queen Conch

House
Bedrooms 4
4 Bathrooms

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.

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