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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

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. 

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.

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.

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.

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.

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.

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

Namaste

House
One Bedroom
2 Bathrooms

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds: relaxing and taking advantage of all that Key West has to offer.

La Brisa #303W

Condo
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium is situated opposite the largest beach on the island, while offering the amenities of a resort hotel.

Map View