Start driving south down US Route 1 and eventually you'll end up in Key West, Florida. The southernmost city in the contiguous US, Key West is part of the string of tropical islands that stretch off the southern tip of Florida known as the Florida Keys. The word key is derived from the Spanish word cayo, meaning "small island."
An island around four miles long and one mile wide, Key West is home to a rich history and tropical temps. With historic landmarks including the Ernest Hemingway House, Harry S. Truman’s Little White House, and the Key West Tropical Forest and Botanical Garden, the island offers plenty to see and do. Airbnb has several unique stays for secluded vacationing but also sports several homes close to the shops in Mallory Square within the heart of Old Town.
Close to Mallory Square in Old Town, this cozy cottage has all the essentials and more. There’s a shared back deck with a heated pool, plus dining tables and chairs for outdoor eating and relaxing.
Fun, bright, and funky, this cottage features two bedroom suites, a cute kitchen (complete with Smeg appliances, and a beautiful free form pool to boot! Plenty of areas for lounging dot the secluded, private courtyard, including a comfy swing in the garden, several lounge chairs, and a large outdoor seating area where visitors can take an afternoon nap or read a good book. When you book this Airbnb, you won't have to venture out too much for a relaxing vacation.
Sit back and relax on your balcony overlooking the attractions on historic Duval Street. Located in the heart of Old Town, this private two-story duplex is a stone's throw from restaurants, live music, and historic sights. Your stay includes a private entrance, access to the pool and grounds, and a complimentary breakfast. One reviewer noted that they felt secure during their stay in July stating, ”the staff are accommodating and quickly responsive. Even in the midst of the COVID-19 pandemic, we felt safe and attended to. We would definitely stay here again!”
An oasis off Duval Street, this centrally located Airbnb is perfect for exploring the island on bike or foot. One of six rooms at Andrews Inn, the Pamplona Room overlooks the historic Hemingway house. Brunch with bottomless mimosas, afternoon happy hour, pool access, and daily housekeeping are all included in the rate.
Situated in the harbor and accessible by water taxi, The Grand Tiki is a unique experience you’ll never forget. Fling open the doors and relax in the ocean breeze, gaze up at the stars from your floating home, and kayak around, exploring the Florida straits.
This charming cottage is within walking distance of the beach, coffee shop, and grocery store. With a gourmet kitchen, rocking chairs on the front porch, and sunny Key West skies you’ll likely want to stay as long as possible. (Which is ideal since this home has a rental minimum of 28 days!)
Starting in Key West, sail the keys in this comfortable yacht for the ultimate sea-loving experience. With three full ensuites, this spacious boat can take you to private beaches in Dry Tortugas National Park. You’ll even have access to scuba gear, stand up paddleboards, and dinghy rides. Bring your own food to prepare or have meals provided for an extra fee.
Moden and private, with a shared pool out back, this cute studio is within walking distance of a cafe, City Marina, and Bayview Park. Your stay also includes two bikes to tool around in. This 100-year-old home is located in a quiet neighborhood with free on-premise parking—a huge plus as finding parking in Key West can be difficult.
Fish off the dock of this waterfront home for a dinner of grouper or snapper. With a full kitchen, private back patio, and access to the canal, this modern home is perfect for families or a couple. BYO boat or rent one to explore the open ocean and canals. According to guests, this superhost may even leave you a slice of key lime pie in the fridge.
Bright, convenient, comfortable, and recently renovated, this apartment is located within walking distance to Key West attractions such as Hemingway’s favorite bar, Sloppy Joes. Enjoy a cup of coffee on the screened-in porch, relax in the courtyard, and stroll to the beach to view the breathtaking Key West sunset.
A delectable French bakery sits across the street from this Airbnb. A private entrance, balcony, shared pool, and free parking are all included in this delightful townhouse, which is located in a gated community. French doors open to an outdoor patio with seating to enjoy your coffee as the sun rises.
Newly renovated, this cute conch cottage is a one-story, private home. Relax in the king-sized bed, grill burgers on the back deck, and eat breakfast in the cozy breakfast nook. Just a few blocks away from the southernmost point in the continental US, you’ll have all the amenities of home, and you can bring your dog!
Grab all of your favorite people and snag this awesome shot-gun home in Old Town. While it is located close to the beach, this home also has a beautiful private saltwater pool for night swims. With a gorgeous gourmet kitchen and great room, you’ll want to stay in this haven indefinitely.