12 Key West Vacation Rentals For The Perfect Island Getaway

Located in the Old Town neighborhood on a beautiful tree-lined street south of Truman Ave, this two-bedroom, two-bathroom vacation home can accommodate up to six guests. People watch from the front porch or enjoy the privacy of the outdoor living area out back that is surrounded by tropical greenery.

Located by Mallory Square in the Historic Seaport area of Key West, this two-bedroom suite can sleep up to six. Do note the seven-night minimum stay with Saturday check-in only. Bringing a boat? The Galleon Resort’s marina offers dockage space for boats and yachts up to 140 feet.

Overlooking the Gulf of Mexico in historic Old Town, this resort features a tiki bar, a waterfront swimming pool, a private beach, an observation deck that offers 360-degree panoramic views of Key West, onsite dining, a workout room, and a sauna.

Only two blocks from Duval Street, the resort is within walking distance of attractions, art galleries, shopping, and restaurants. Fishing charters, sunset cruises, parasailing, snorkeling, dolphin watching, glass-bottom boats, and jet ski and scooter rentals are all available at the marina or nearby.

A little further out on Stock Island, this peaceful retreat requires a 30-night minimum stay. Situated off of the 17th fairway in a gated golf course community, this spacious home provides a quiet oasis for up to six guests and two dogs.

Highlights include a pool with an oversized deck, porch, and sundeck, lush tropical landscaping, and views of the golf course lake from the den. Watch the sunrise from the rear upper balcony or lower porch.

Duval Street, beaches, and Conch Harbor are just a few minutes away by car. Round-the-clock security and two off-street parking spaces are provided. If this Stock Island stay is booked for your desired dates, check out this other two-bedroom townhome in a golf course resort.

Those who want to steer clear of the crowds should check out this oceanfront property in Raccoon Key. Up to eight folks can stay in its four bedrooms. There isn’t a pool, but there is a ladder on the sea wall so that guests can swim or kayak in the canal. You can even bring your own boat and/or well-behaved pet.

Sunbathe on the beautifully landscaped courtyard, dotted with palm trees. Pick some fresh key limes from the key lime tree. Beaches, restaurants, and the Key West Golf Club can all be found nearby.

Also located in the gated community of the Truman Annex, this lovely two-bedroom, two-and-a-half-bath vacation home requires a seven-night minimum stay. The main bedroom features a private deck that overlooks the lovely outdoor area. Surrounded by lush tropical landscaping, the deck has both a covered seating area as well as a picnic table.

One parking space is provided out front, but all of the action of Old Town, including dining, shopping, watersports, and nightlife is close by. It’s also just a quick walk to the common area pool!

This three-story townhome can be found in the Truman Annex neighborhood of Old Town. With two bedrooms and two and a half baths, it can accommodate up to six guests. Do note that this vacation rental requires a minimum stay of seven nights.

Mallory Square, Truman Waterfront Park, Fort Zachary Taylor, Truman’s Little White House, and hot spots such as Green Parrot Bar are just steps away. Its also within four blocks of the action-packed 200 block of Duval Street.

Part of The Foundry Building, the unit has a gated entry and courtyard. It also comes with two bikes for tooling around the island and one designated parking space. Plus, the complex has a pool that can be found right across the street.

Just steps from the heart of Duval Street and Truman Waterfront Park, this ground-floor apartment is in a gated community in Truman Annex. This two-bedroom unit features a community pool, 24-hour security, and one parking spot. A 28-night minimum stay is required.

All of the best Key West attractions, including Mallory Square, Fort Zachary Taylor, The Hemingway Home and Museum, the Historic Seaport, and the Southernmost Point, are within walking distance.

Going with a group? This 100-plus-year-old compound in Old Town can accommodate up to 23 guests between its 10 bedrooms and in four separate houses on the property. The catch? There are only three and a half bathrooms. Highlights include a heated pool and jacuzzi, wraparound porches on both floors of the two-story main house, and a sundeck. Located near Fort Zachary Taylor Historic State Park Beach, two off-street parking spaces come with this vacation rental.

Near all the Old Town action, this adorable one-bedroom, one-bath cottage sits in a quiet residential neighborhood just a few blocks from Duval Street. Surrounded by tropical greenery, it features a professionally decorated interior and a private deck where you can get some sun or dine al fresco.

Stay near the action in this Key West vacation rental just half a block off of Duval. This three-bedroom, two-bath home is within walking distance of restaurants, beaches, and attractions such as the Southernmost Point and The Key West Butterfly and Nature Conservatory. Cool off in the private lagoon-style pool out back. The only catch? There is a six-night minimum stay.

Located one block from Duval Street, this downtown cottage is part of the Center Court Key West. The pool is shared with other guests, but you get a hot tub and deck all to yourself. Key West attractions like the Ernest Hemingway Home and Museum, Key West Butterfly and Nature Conservatory, and Southernmost Point are all within half a mile, so you can walk or bike instead of driving or taking a rideshare.