Last Updated on November 16, 2020
Planning a Key West getaway? This island, the southernmost point of the continental United States, is known for its history, nightlife, beaches, and colorful “Conch-style” architecture. Get tips on the best Key West Airbnb stays to help you make the most of your Florida vacation!
This year more than ever, people are exploring Airbnbs as a travel accommodation option. Airbnbs let you experience a destination more like a local, and offer practical amenities versus a traditional hotel, such as kitchens, living and dining spaces, and private entrances. Some Key West Airbnbs even have luxury amenities like pools, hot tubs, and unconventional spaces – so I’ll be sure to recommend some with these options as well!
Whether you’re looking to stay close to the action of Duval Street, catch some sun on Key West’s beaches, or relax with family, these Key West Airbnbs will give you a private space as a home base for your adventures. Get ready for the best Key West vacation rentals, budget cottage hideaways, and luxury homes!
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Key West Not-to-Be-Missed Activities
If you haven’t yet finalized your Key West itinerary or if you’re looking for more tips on activities, be sure to consider these top sights when you plan your stay:
- Hemingway Home & Museum: Learn about the influence that Key West had on Ernest Hemingway’s writings and meet the famous poly-dactyl cats that still rule the property.
- Key West Butterfly and Nature Conservatory; This fascinating learning center and conservatory lets you learn about butterflies and then experience them in a beautiful habitat along with birds including flamingos. (No joke, this is where I learned that Peru has the most butterfly species of any country!)
- Key West Ghosts & Gravestones tour: Did you know that Key West is reported to be one of the most haunted cities in the U.S.? Explore Key West’s darker side with this tour.
- Key West Half Day Snorkeling: Experience North America’s living barrier reef and see up to 600 species of colorful fish, coral, and other sea life with this excursion.
- Dry Tortugas National Park day trip. Be sure to check out my full guide to visiting the pristine beaches and snorkeling at one of our nation’s most remote national parks!
- Key West Sunset Sail: This would be a perfect activity for your last night in Key West! See the sun set and enjoy a private catamaran trip with live music, a full bar & hors d’oeuvres.
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In this Key West Airbnb Guide:
Best Key West, Florida Airbnbs for Couples & Solo Travelers
Planning a honeymoon or romantic getaway? Taking a trip with a friend, or exploring solo? These Airbnbs are perfect for up to 2 travelers.
Mango Hideaway steps to Duval Street with hot tub
Mango Hideaway, a pet-friendly Key West Airbnb, is located a half block from Duval Street. It has a kitchenette, king bed, private hot tub, and shared pool access. Parking is available (request at time of booking). This is a mid-range option with plenty of space for two in a great location!
Tiny House Studio in perfect location
This private modern “tiny house” studio is just a block from the Hemingway House and within walking distance of all the shops, restaurants and sights of Duval Street. It has a queen bed, kitchenette, cable tv and WiFi. No parking, but this is an awesome budget stay in an amazing location (and so cute!).
Honeymoon Hideaway with private spa
The Honeymoon Hideaway is perfect mid-range option for solo travelers and couples and is located on a quiet side street off Duval. It features a king bed, kitchenette, and private deck with a 2-person spa. There’s also access to two pools in the community.
1-Bedroom Key West Cottage in great location
Located in the heart of Key West, this cute cottage features a queen bedroom, sofa bed, full kitchen, and an option for reserved parking. It gets rave reviews for the thoughtfulness of the hosts, sparkling cleanliness, reasonable price, and great location.
Poolside Studio Villa Steps from Duval Sreet
This private room in the Key West Villas has a bright cheery design, queen bed, and full kitchen. You’ll enjoy relaxing at the shared pool or taking in the sights of Duval Street, just a half block away.
Key West Airbnb Stays for 4-6 guests
These centrally-located Key West condos, cottages and houses are perfect for larger groups up to 6 people.
Key West Suites Hotel: 3 bed studio on Duval Street
This charming yet affordable studio apartment overlooks Duval Street! With 2 king beds and one queen sofa bed in the studio space, it accomodates 4-6. This Key West Airbnb gets rave reviews for its location and is great for a family with young children.
Casa Cristol: 3 bedrooms with shared pool
Casa Cristol is a mid-range, secluded family-friendly retreat just a block away from Duval Street. With 3 bedrooms and 3 baths, it’s perfect for a family getaway. Includes a spacious kitchen, living area, private lanai, and parking for one car. Its shared pool is steps away inside the gated community.
Fleming-O Cottage: 2 bedrooms with outdoor living space
Fleming-O (pronounced “Flamingo”) is located on Fleming Street in the middle of historic Old Town Key West and only two blocks from Duval Street’s restaurants, bars, art galleries, and shops. This affordable conch cottage has a full kitchen, two bedrooms and sleeper sofa, and one bath. Its outdoor space includes a private deck with a gas grill, chaise lounges, built-in benches, an outdoor dining table, and outdoor shower.
Hidden Treasure Cabin: 2 bedrooms with shared pool
This charming mid-range conch cottage has two king bedrooms, a sleeper sofa, two baths, and a full kitchen. Its outdoor spaces include a lush garden with pond, private seating area, gas grill, and shared pool. Hidden Treasure is the perfect spot to unwind within walking distance of all of Key West’s charms.
Airbnb Key West Stays for 6+ Guests
If you’re getting together with family or friends and need more space, these Airbnb Key West, Florida rentals have all the amenities needed for a relaxing trip.
Casa Loca: 3 bedrooms with private pool
Casa Loca is a stylish space sure to wow: just check out its elegant island vibes and private heated courtyard pool! Casa Loca Airbnb has 3 bedrooms plus a sleeper sofa and accommodates up to 8, making it perfect for a family or friends gathering. Located just a short distance to all the sights of Duval Street, in the heart of Old Town Key West.
5-Star Getaway: 4 bedrooms with private heated pool
This newly-renovated 4-bedroom home is perfect for a family with older kids or for a group of couples. It has 3 bedrooms in the main house, while a 4th bedroom and a full bath is located in the guest cottage. The outdoor space includes a courtyard perfect for entertaining and relaxing around the heated pool. Located just a few blocks from the Harry Truman Little White House, where President Truman spent 175 days during 11 winter visits.
Key West Hideaway: 4 bedrooms with shared pool
This historic Key West home from 1874 has been completely renovated with modern conveniences including a gourmet kitchen, smart TVs in each bedroom, and access to two heated pools. Located just a half block from Duval Street, this classy yet comfortable space is perfect for a relaxing getaway with family or friends.
Casa Grande: 5 bedrooms with private pool
The owners of Casa Grande say it was built for hosting large gatherings of family and friends! It’s the perfect space for relaxing in privacy and gathering together in its spacious living room, gourmet kitchen and pool – one of the largest private pools on the island. Less than one block from Duval Street, you can stroll or bike to all the best the island has to offer. Casa Grande also has two reserved parking spaces, which are in extremely short supply in Old Town!
Unique Airbnb Key West Stays
Do you like quirky getaways and unexpected spaces? Check out these truly unique Key West Airbnb stays!
The Tiki Suite
This off-grid houseboat stay might be the most unique Key West Airbnb! Envisioned as “glamping on the water,” the Tiki Suite lets you relax on deck in a hammock, stand-up paddleboard, snorkel, and bird watch. Access is via water taxi and amenities are limited – check the listing for details if this sounds like your kind of adventure!
Ready to book your Key West, Florida trip?
Don’t miss my guide on how to plan a day trip to Dry Tortugas, one of the most remote U.S. National Parks. Get tips on booking a ferry to experience pristine beaches, snorkeling ,and even overnight beach camping!
Last Updated on October 26, 2020 During a vacation to the Florida Keys, I took a day trip from Key …
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