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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

Dreaming on Duval IV

House
Bedrooms 4
3.5 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.

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.

Townhomes on Windsor #3

Villa
Bedrooms 3
3.5 Bathrooms

Once you enter this newly renovated and professionally decorated oasis…your vacation begins. This property has been created to meet your every need. The location is simply perfect: just three short blocks from Duval and tucked away on a quiet lane so you can choose your level of activity.

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.

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.

Map View