Vacation Rentals in Key West - Page 6 of 13

This canal-side modern estate is sanctuary living at its finest. Located on the island's only canal, this property features 3 separate master suites, modern gourmet...

Our 2bed/1 bath condo in the lovely gated community of Truman Annex provides the perfect way to experience Key West- like a local.

Historic charmer, one block from Hemingway's home, great location, and off street parking for two cars. There is historic context to Ernest Hemingway with this home.

The timeless charm of this distinguished Classic Revival mansion is at once authentic and magnificent. If you have ever had the opportunity to stroll the historic...

Beautiful courtyard property with pool just steps off Upper Duval St. in Historic Key West You would never know this private hidden compound is just one block off...

The Grande Dame Key West is by far one the rarest and most exclusive private estate residences in Key West offered as a licensed single-family vacation home. An...

You’ll be carried away by the stunning ocean views from this luxurious Key West condominium. Make your first order of the day to breathe in the fresh ocean breezes...

Swim, boat, fish, dive, sun and relax while staying in this stunning and newly renovated Key West ocean front home.  Walls of glass look out over the ocean from...

This charming property is located in the historic Old Town Upper-Duval Street neighborhood. This quadrant of our island offers excellent gourmet restaurants, gallery...

Rare one-of-a kind designer luxury suite located in an exclusive gated beachfront property. Breath taking views overlook the ocean and natural aquatic bird...

This beautiful historic home is conveniently located in a quiet Old Town neighborhood, just a few steps from the galleries, restaurants and shopping of the White...

Originally built in 1938, this fully renovated luxury home is a spectacular ‘show piece’ and one of the most creative designs in Old Town Key West.

An artist-owner's delightful design and renovation of a carriage house has created an adorable intimate two-story, one bedroom fantasy island cottage.

Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off the large gated garden.

'Vintage Luxury Cottage' - Just Off Upper Duval Street - Private Renovated Cottage with Private Pool Without a doubt, one of the rarest private Key West vacation...

Ideally situated in the Historic Seaport side of Old Town Key West, this 1 1/2 story Classic Revival Shotgun Island cottage is located in one of the most charming...

Lilly's Pad is beautifully decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story with hardwood floors, a...

A Private Tropical Paradise. . . is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St.

Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront condominium set in a topical garden paradise...

Newly remodeled condominium located in the Truman Annex Complex, which is 2 blocks from Duval Street and all of the Old Town Key West attractions.