Key West is a tropical paradise perfect for those craving a long escape from the harsh winter weather (we’re looking at you, snowbirds!). With its sunny beaches, crystal-clear waters, and vibrant nightlife, there are plenty of things to do in Key West for visitors to enjoy. Whether you’re desiring a relaxing day by the beach, an adventure out on the water, or a night on the town, Key West is an idyllic destination for a vacation.
For those looking to get away for a month or more, we’ve rounded up our favorite vacation homes available for an extended stay. These AvantStay vacation rentals have everything you could need in your home away from home, including a fully-equipped kitchen, hotel-grade amenities, a washer and dryer, bedding and linens, WiFi, and access to our 24/7 guest experience line as well as a local hospitality manager.
Here are our top picks for vacation homes for snowbirds in Key West:
1. Salty Palm Retreat
Set within the gated Shipyard Condominium community in Truman Annex, Salty Palm Retreat brings an easy, breezy rhythm to an extended Key West stay. This two-bedroom home pairs Old Town charm with the practical comforts of a home away from home, including a well-equipped kitchen, comfortable gathering spaces, and a shaded porch surrounded by tropical greenery. Guests can cool off in the shared community pool or head out on foot to explore the island. Fort Zachary Taylor Historic State Park and its popular beach are a short walk away, while Duval Street, Mallory Square, and many of Key West’s best restaurants and attractions are also within easy reach. It is a relaxed base for settling into island life at your own pace.
2. Buttonwood Corner
Buttonwood Corner offers a private Midtown retreat with plenty of room to enjoy the Key West lifestyle. The three-bedroom, two-bathroom home features a bright, open living space where guests can gather after a day around the island. Outside, the private pool, dining area, and grill create an inviting setting for sunny afternoons, casual dinners, and warm evenings under the palms. Its Midtown location places beaches, restaurants, shopping, and island attractions within easy reach, while still providing welcome distance from the busiest parts of Old Town. With space for up to six guests and a laid-back indoor-outdoor setup, Buttonwood Corner is a comfortable choice for families or friends planning a longer stay.
3. Serenity
Located in Bahama Village, Serenity is a beautifully renovated conch-style guest cottage designed for a peaceful couples’ escape. The two-story home includes one bedroom, one bathroom, a bonus loft, and a full kitchen, making it easy to settle in for an extended visit. High ceilings and glass doors fill the cottage with natural light, while the secluded tropical garden creates a private island oasis. Guests can lounge beside the heated pool or refresh in the open-air outdoor shower. Duval Street is only a few blocks away, so restaurants, nightlife, and historic attractions are close at hand, yet the cottage remains tucked away from the busiest crowds. The result is a romantic retreat that feels both connected and wonderfully calm.
4. Easy Livin’
Easy Livin’ lives up to its name with an upscale but comfortable setting in the gated Truman Annex community. This three-bedroom home has generous indoor and outdoor gathering spaces, a fully equipped kitchen, and a private saltwater pool that makes relaxing at home just as appealing as exploring the island. The secluded cul-de-sac setting offers privacy, while the Old Town location keeps Key West favorites within walking or biking distance. Spend mornings by the pool, afternoons at Fort Zachary Taylor, and evenings dining or listening to live music near Duval Street. With four bathrooms and room for up to eight guests, Easy Livin’ is especially well suited to families and groups looking for space, convenience, and a true residential Key West experience.
5. Key West Found
Key West Found is a spacious two-bedroom, two-and-a-half-bathroom townhome inside the historic Foundry building. Spread across three stories, the home blends whimsical island style with the room and amenities guests appreciate during a longer stay. A private front porch framed by tropical landscaping is an ideal place for morning coffee or an evening cocktail, while the community pool offers a refreshing break from the Florida sun. The location is one of the home’s biggest draws: Harry S. Truman’s Little White House is just steps away, and Mallory Square, Duval Street, waterfront dining, and Old Town attractions are all nearby. For guests who want history, character, and walkability, Key West Found makes a memorable island home base.
6. Beach House Condo
Beach House Condo is a charming two-bedroom, two-bathroom ground-level home in the gated Shipyard Condominium section of Truman Annex. Designed to feel like a comfortable home away from home, the condo offers an equipped kitchen, welcoming living spaces, and a spacious back deck for slow mornings and laid-back evenings. Guests also have access to the community pool, perfect for cooling off between island adventures. From this central Old Town location, it is easy to walk or bike to Fort Zachary Taylor, Duval Street, Mallory Square, and the neighborhood’s many restaurants and historic sites. With room for up to five guests, Beach House Condo works well for couples, small families, or friends who want a convenient and relaxed extended stay.
7. Shipyard Treasure
Shipyard Treasure brings a bright, easygoing atmosphere to an oversized second-floor condo in the heart of Old Town. The two-bedroom home is set within the sought-after Shipyard community and features comfortable living areas, a full kitchen, and two breezy decks where guests can enjoy the tropical surroundings. A shared pool is nearby for leisurely afternoons at home. When it is time to explore, the Historic District’s restaurants, shops, waterfront, and famous attractions are all within walking or biking distance. The combination of residential comfort and a highly walkable location makes Shipyard Treasure a strong choice for guests who want to experience Key West beyond a quick weekend and settle into the island’s slower, sunnier pace.
8. Key West Charming
Key West Charming is a welcoming first-floor condo in the Shipyard community of Truman Annex. This two-bedroom, one-bathroom home features a comfortable living and dining area that opens onto a large private wooden deck, creating a sunny outdoor space for reading, relaxing, or enjoying an unhurried meal. The well-equipped kitchen supports easy nights in, while the community pool provides another spot to unwind. The primary bedroom has a queen bed, and the second bedroom has two twin beds, making the layout convenient for a small family or group of friends. Its downtown location keeps Duval Street, Fort Zachary Taylor, Mallory Square, and many Old Town favorites close by throughout an extended stay.
9. Lavender Jungle
Lavender Jungle is a distinctive two-bedroom, one-bathroom first-floor condo in the Shipyard section of Truman Annex. True to its name, the home combines purplish-pink tones, African-inspired artwork, and tropical character to create a space that feels playful, warm, and unmistakably Key West. A spacious modern kitchen makes longer stays convenient, while the shared community pool is ready for afternoons in the sun. The quiet neighborhood offers a restful place to recharge without giving up easy access to the action. Duval Street, Old Town dining, historic landmarks, and Fort Zachary Taylor are all within walking or biking distance. Lavender Jungle is an inviting option for guests who appreciate personality, color, and a central island location.
10. La Casita
La Casita is a charming two-bedroom retreat tucked onto a quiet lane in the heart of Old Town. The location makes it easy to experience Key West like a local: Blue Heaven, the Ernest Hemingway Home and Museum, the Key West Lighthouse, and Duval Street are all just around the corner. Inside, thoughtful design and a fully equipped kitchen create a comfortable setting for a longer visit. Outside, a tropical landscaped courtyard offers a peaceful place to start the morning or unwind after exploring the island. With so much available on foot or by bike, guests can settle into a relaxed routine without needing to travel far. La Casita is a cozy and convenient choice for couples or a small group seeking an authentic Old Town stay.
These ten homes offer different ways to enjoy a longer Key West escape, from private-pool retreats to historic Old Town condos within walking distance of the island’s best-known sights. Explore more AvantStay vacation homes in Key West and find the space that fits your extended island stay.