Key West Vacation Rentals

There's something special about the kind of comfortable living afforded by this four bedroom, 2.5-bath, single-family home designated as "Lady Emma." The house takes its name from the street it inhabits, one of the most desirable addresses in town. It's part of Truman Annex, an award-winning...

If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies,...

Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting with tropical...

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing...

If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...

Impressive. Distinctive. Comfortable. The perfect spot for your tropical get away. This second floor, two bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the quintessential indoor/outdoor vacation experience you've come...

Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island...

Cozy, comfortable, affordable. Not to mention a location in the very heart of the Historic District of Upper Duval. That's why this one bedroom/one full bath rental is aptly named Bella Vita, the beautiful life. Located within La Casa de Luces building, Bella Vita features a...

Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell Suite, a second & third floor condo with one bedroom and 1½ baths, is the perfect place to anchor your vacation. It starts with the white...

Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-bath estate, is all about. The house and private grounds and off-street parking occupy a whole city block of historic Old Town, exceptional spaciousness on the small island of Key West. Copious...

This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and proximity...

Looking for an ideal vacation? This charming three-bedroom, three-bath home is the perfect getaway spot. The style? A classic Key West eyebrow with two saw-tooth additions and plenty of Dade County pine. The story? The name "Maximo Cabana" commemorates Maximo Diaz, who bought the house in...

This three-bedroom, three-full-bath cottage exudes the kind of at-ease ambiance that tells you you're right where you need to be to have the best vacation ever. The cottage is in the Meadows neighborhood on the grounds of an impressive Key West estate. Like something out of...

Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom, two-full-bath conch cottage in Old Town Key West. Recently restored and updated to include amenities such as a heated pool with rainforest waterfall, granite counter tops,...

For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and modern functionality. The pool and...

Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath condo is near the center...