Key West is the ideal Florida beach destination, combined with history beautiful houses, and fantastic restaurants.
Connected to the mainland via 48 bridges, this island offers an abundance of outdoor activities, beautiful beaches, the historic streets of Old Town, and lots of cycling trails.
We’ve put together a list of our 15 favorite AirBnBs in Key West that you can book for the perfect Florida vacation!
Whether you are traveling to Key West by yourself, as a couple, with a large group of girlfriends, or for a bachelorette party, you can find the perfect Key West AirBnB to stay in no matter what the season!
Here’s a quick summary of the best Airbnbs in Key West:
- Best for a Bachelorette Party: Casa Victoria
- Best for Families: Pet Friendly Rental
- Best for Couples: Mango Cottage
- Most Unique: The Tiki Suite
- Best Location: Mermaid Cove
Best AirBnBs for Bachelorette Parties and Large Groups
Commodore’s Manor
The Commodore’s Manor is a 3,500 square foot townhouse located on the waterfront in Garrison Bight, Paradies Harbor.
The house is located within walking distance of Old Town and its attractions, including restaurants, shops, and grocery stores.
This townhouse is ideal for a bachelorette party, celebrations, event, or girls’ getaway, with five bedrooms and the ability to sleep up to 14 people.
The five bedrooms are made up of a bedroom on the first floor with two twin beds, two bedrooms on the second floor with a king and queen bed.
The third floor has two other bedrooms, one with two twin beds and the other with four twin beds. All the twin beds have the ability to be converted into king beds.
Inside the house on the first floor is a large room with a large living room area, a kitchen with a large breakfast bar, and a balcony with a dining table.
Outside the house, there is a large swimming pool, outdoor dining table, sun loungers, a boat slipway, a view of the water, and a dock.
- Location: Paradise Harbor
- Sleeps: 14 guests
- Size: 5 bedrooms / 6 beds / 4 baths
- Price: Check Latest Prices
Featured Guest Review: “We had a great stay in Key West. The house was huge and was very beautifully decorated and clean. The host was very kind, gave us lots of local tips, and even gave us a key lime pie.” – Kelly
Casa Victoria
Casa Victoria is a traditional Conch House, that is perfect for a bachelorette party, girls’ getaway, family trip, or friends trip, with up to 12 people.
The house has five bedrooms, two with king beds and en-suite bathrooms, the third floor has a bedroom with a queen bed.
The fourth bedroom has two queen beds, and the fifth bedroom is within a separate guest cottage and has a king bed and en-suite bathroom.
This house is filled with color, bright greens, blues, reds, yellows, and oranges.
Inside the house, there is a living room area, which leads into a dining area with enough room for 8 people. There is also a large kitchen area, and five and a half bathrooms.
Outside there is a large undercover dining area, which is perfect for an al fresco dining experience.
There is also a swimming pool and a sun deck surrounded by sun loungers and a hot tub area.
Casa Victoria is located just a few blocks from Duval Street, with close access to restaurants, museums, nightlife options, bars, and local amenities.
- Location: Old Town
- Sleeps: 12 guests
- Size: 5 bedrooms / 6 beds / 5.5 baths
- Price: Check Latest Prices
Featured Guest Review: “The house was beautiful and in a great location. We enjoyed the back yard, pool & jacuzzi. Great location & service and we would stay there again. Thank you!” – Shane
Endless Summer
This cool house is a great place to use as a base and somewhere to relax after a day exploring Key West and the Florida Keys.
It is also a great place to stay on a group trip, whether that be on a bachelorette house, a girls’ getaway, or a family trip.
Located in Old Town, just a half a block from Duval Street, with lots of dining options, bars, and things to do.
From the house, you can explore the local area, or just ride bicycles around the town. The house is located at the end of a lane, which provides lots of privacy for a peaceful trip.
With five bedrooms, this house can sleep 12 guests comfortably with lots of space.
Three of the bedrooms have two twin beds which can be pushed together to make a king bed. Another bedroom has a queen bed with an en-suite bathroom and the fifth bedroom has a king bed with a private balcony.
The house has a large living room which has three-doors that open out into the swimming pool area.
There is also a small dining table with four chairs. The kitchen area is large and fully equipped with everything you need to cook meals for your group.
Outside there is a large decked area that has a dining table, BBQ grill, and leads out into a rectangular swimming pool with sun loungers.
- Location: Old Town
- Sleeps: 12 guests
- Size: 5 bedrooms / 6 beds / 5 baths
- Price: Check Latest Prices
Featured Guest Review: “From the amenities to the little extra touches this house checked all the boxes. Add in super sparkling clean and a to-die-for location and the perfect vacation is yours. And I can’t leave out the amazing concierge service or our host, Greg.” – Paula
Mermaid Cove
Mermaid Cove is a collection of four cottages, each one has an entrance, courtyard, and outdoor patio.
This is the perfect place to stay if you want to have a group trip but would like your separate space. Each of these four cottages has a different number of beds.
The first cottage has a king and sofa bed, the second has a queen bed, the third has a king bed, and the fourth has two queen beds.
Each cottage is decorated with charming tropical fashion. The cottages are named Mermaid, Funky, Ocean, and Nautical.
Cottage 1 has a full kitchen while the other cottages only have mini kitchens.
In the courtyard, there is a large grill, outdoor stainless steel sink, a dining area, and plenty of room.
Located on Duval Street, in the heart of Old Town, this area has lots of restaurants, art galleries, beaches, bars, museums, breakfast options, and even a smoothie bar.
- Location: Duval Street
- Sleeps: 12 guests
- Size: 4 bedrooms / 6 beds / 4 baths
- Price: Check Latest Prices
Featured Guest Review: “Super cute set of cottages in a great location in Key West. Clean, within walking distance to several attractions, adorable shops, & great restaurants and able to accommodate our larger party with a nice common courtyard.” – Renee
Seaside Place
This classic Key West style home with custom woodwork furniture, is 2,700 square feet, traditional balconies, five bedrooms, and six bathrooms.
Ideal for up to 10 guests whether that be on a bachelorette party, girls’ getaway, family, trip, or any other event.
The five bedrooms are a mix of queen-sized beds and king-sized beds.
The house has a large kitchen area, with a bench table, a living room area with bright walls, and beautiful artwork. There is also a separate area with a bench and a small table.
This house is filled with bright colors, artwork, and unique decorative pieces in each room.
Upstairs there is a balcony with outdoor furniture, and on the ground floor, there is a porch with chairs.
Outside there is a large swimming pool, with an outdoor bathroom, an undercover dining area with a BBQ grill.
Around the pool, there are multiple sun loungers and outdoor seating areas, perfect for enjoying the beautiful Florida weather!
- Location: Duval Street
- Sleeps: 10 guests
- Size: 5 bedrooms / 7 beds / 6 baths
- Price: Check Latest Prices
Featured Guest Review: “What a STUNNER! This house was massive, gorgeous, and went WAY beyond my expectations! Beautiful rooms! An incredible private heated pool!” – Kristen
Pet Friendly Vacation Rental
Located just off Duval Street, this vacation rental is filled with light and bright colors. This Airbnb has a main house and a smaller guest house.
The main house has two bedrooms, both with queen beds and two bathrooms. The smaller guest house is a studio with a queen bed and sofa bed.
The house has a large living room area with plenty of sofa space and a dining room. The kitchen has ample space and is fully equipped with everything you need.
Outside the main house, there is a large deck area with a dining table, and there is also a swimming pool with sun loungers and a BBQ grill.
The smaller house has a mini kitchen, with a small dining table, bathroom, and bedrooms.
This rental is also one of the few pet friendly properties so you can bring your dog on your Florida vacation!
This house is in the ideal location for exploring the local area, just four blocks from the beach, walking distance to shops, restaurants, museums, and historical sites.
- Location: Duval Street
- Sleeps: 8 guests
- Size: 3 bedrooms / 4 beds / 3 baths
- Price: Check Latest Prices
Featured Guest Review: “What a wonderful escape! Perfect location, easy walking distance to everything. Great set up with the cottage. It enabled us to all vacation together without being on top of everyone.” – Sherry
Best AirBnBs for Small Groups and Families
Beach Club Ocean Front Condo
Ideal for a small group getaway, family trip, or a small group of friends, this beachfront Airbnb has two bedrooms sleeping up to five guests.
This oceanfront condo has an open plan living, dining, and kitchen area.
The kitchen is fully equipped with everything you need for your stay, and the living area has two bio-folding doors that open out onto a large balcony. The balcony has oceanfront views and outdoor furniture.
The two bedrooms in this condo area made up of one with a king bed and the other with a king bed and single bed.
Located within the Key West Beach Club the condo has access to one parking space and the club’s facilities, which include two swimming pools, a tennis court, outdoor cooking facilities, a fitness room, sauna, and within walking distance of the beach.
The club is also located within walking distance of restaurants, and a short bike ride from Old Town with its local markets and shops.
- Location: Key West Beach Club
- Sleeps: 5 guests
- Size: 2 bedrooms / 3 beds / 2.5 baths
- Price: Check Latest Prices
Featured Guest Review: “If you want to see the ocean then you can not beat this place. It’s a large apartment with two very good sized bedrooms. It’s a gated community and the pools are wonderful as well as the views.” – Jp
Mango Cottage
Mango Cottage is a recently restored traditional Key West Conch house with antique pine walls, and two bedrooms, ideal for sleeping up to 6 people.
his house is great for a family trip or a small group getaway with the girls.
The two bedrooms are made up of one with a queen bed and one with a king bed. There are also two single beds in the common spaces.
The house is spacious with an open living, dining, and kitchen area. The kitchen is fully equipped with everything you need and decorated in light colors and blues.
Outside there is a small deck area with a dining table, sun loungers, and a small swimming pool.
- Location: Old Town
- Sleeps: 6 guests
- Size: 2 bedrooms / 2 beds / 2 baths
- Price: Starting from $540 per night
Featured Guest Review: “Everything about this place was fantastic! Highly recommend to anyone! Perfect location within walking distance of many major attractions. Great amenities! Easy check in and out!” – Melissa
Casa Cristol
Located just one block from Duval Street, this house is close to shops, restaurants, and local amenities. It is located within a gated community called The Truman Annex.
This house is perfect for families with three bedrooms that can sleep up to 6 people. One bedroom has a king bed and two have queen beds.
The kitchen is fully equipped with a large dining area that opens up into the living room area. The living room is large with two big sofas and large floor to ceiling windows and doors.
Outside the house, there is a deck area with a dining table, BBQ grill, plenty of plants, and a shared swimming pool area.
- Location: Key West Truman Annex
- Sleeps: 6 guests
- Size: 3 bedrooms / 3 beds / 3 baths
- Price: Starting from $427 per night
Featured Guest Review: “A perfect place for a family or couples vacation. There’s plenty of room and the house is lovely. Best of all is the location. So close to Duval and all the tourist attractions.” – Clare
Best AirBnBs for Solo Travelers and Couples
The Bartlum
Located on Duval Street, this private studio is a great place to base your Key West vacation!
From here you can tour the island, grab a bite to eat, go snorkeling, swimming, fishing, or paddleboarding in the ocean. You can also enjoy everything the area has to offer.
Whether you are traveling as a couple or a solo traveler, this rental has a large bed, a sofa, a dining table, and a fully equipped kitchen.
The studio is very spacious and filled with natural light. The walls are painted white, with red and blue features.
This apartment is very large and spacious with lots of free space.
- Location: Duval Street
- Sleeps: 4 guests
- Size: 1 bedrooms / 2 beds / 1 baths
- Price: Check Latest Prices
Featured Guest Review: “The Bartlum was the perfect place for my husband and I to stay for a short get away. The location is PRIME! 1/2 block walk to Duval Street, walkable to many sites, restaurants and touristy spots.” – Beth
Best Unique AirBnBs
The Tiki Suite
One of the most unusual AirBnBs on our list, this Tiki Suite is located in a harbor on the water, accessed by a water taxi!
The Tiki Suite was made to be a glamping experience on the water, with a tropical-themed feel, Brazilian hardwood floors, and thatched-hut style roofing.
With a king-sized bed, high vaulted ceilings, and three French doors that open out onto the ocean.
From the room, if you are lucky you might see dolphins, manatees, or stingrays. You can also go stand-up paddleboarding or snorkeling.
This glamping experience is the ideal off the grid destination, with minimal appliances, with a roto-molded cooler, coffee machine, a bathroom, air conditioning, wifi, and electricity.
The Tiki Suite also has a hammock and chairs outside, ideal for watching the sunset or sunrise on the deck with a morning coffee or evening glass of wine.
- Location: Key West
- Sleeps: 2 guests
- Size: 1 beds / 1 baths
- Price: Check Latest Prices
Featured Guest Review: “The Tiki Suite was just spectacular. Definitely would recommend to anyone looking to retreat and disconnect for a couple of days. Loved this experience so much!” – Cami
48′ Yacht
This 48 foot yacht is located in one of the best marinas in Key West! The marina has swimming pools, a hotel, live music, restaurants, and full services.
The marina is also located close to downtown with lots of restaurants, shops, and there is a free shuttle from the marina to downtown.
The yacht has a kitchen, living area with a double sofa bed, a dining area, a bathroom, a shower, and four bedrooms.
The yacht can sleep anywhere between two and ten people, ideal for a family or a unique friend’s trip.
You can use the boat to set sail and explore nearby beautiful beaches if you don’t have sailing qualifications you can hire a captain.
The unique Airbnb offers different excursion packages so you can choose what works best for you!
- Location: Key West
- Sleeps: 11 guests
- Size: 4 bedrooms / 6 beds / 4 baths
- Price: Check Latest Prices
Featured Guest Review: “This is special! A beautiful boat with all the mod cons, in a lovely location and the additional benefits of a lovely hotel complex alongside. Highly recommend. Push the boat out if you can and go for it!” – Wayne
The 10 Best Things To Do In Key West, Florida
To help you make the most of your trip to Key West, here are 10 of our favorite activities in the city:
- Visit Mallory Square, with street performers, musicians, food vendors, restaurants, and entertainment.
- Explore Ernest Hemingway’s historic house, which was his house from 1931 to 1939. Here you can also learn all about the history of the area.
- Climb to the top of the Key West lighthouse and take in the views.
- Visit the Key West Butterfly & Nature Conservatory, filled with tropical plants, birds, and butterflies.
- Taste Key West rum, at the Key West First Legal Rum Distillery.
- Relax on a beach, Smathers Beach, Fort Zachary Taylor Beach, Higgs Beach, or Rest Beach are good options.
- Visit the Southernmost Point.
- Take to the water, whether that be on a boat trip, a paddleboard, sunset cruise, catamaran cruise, or an Eco Tour of the mangroves.
- Explore Duval Street with lots of dining options, shops, sample key lime pie, historic homes, the area also holds events and festivals throughout the year.
- Take a day trip to Dry Tortugas National Park, to go snorkeling in the seven reef islands, and the 19th-century Fort Jefferson.
For more things to do in Key West, check out our The Best Of Key West Guide and Florida Keys Road Trip articles!
Ready To Book Your Stay?
Key West is the perfect destination for a weekend getaway, family reunion, bachelorette party, or a girl’s getaway in both the winter and summer.
If you want to plan the ultimate Florida getaway, be sure to also check out some of the best Airbnbs in Miami.
Be sure to check our growing Airbnb Directory for all of our favorite places to stay.
Do you know of a unique AirBnB that belongs on our list? Let us know in the comments below!
Ready to go to Florida? Read on for more inspiration
- 5 Fantastic Florida Kayak Escapes
- The Best Of Key West – Beyond Duval Street
- Dry Tortugas National Park: A Fortress In The Sea
- How To Have The Perfect Florida Keys Roadtrip
- The Best Things Central Florida Has To Offer
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Kelsey says
LOVE this post! Hoping that one day I will get the chance to go to Key West! I think I like Casa Victoria the best!