Best Key West Airbnb - Airbnb Key West Fl - Airbnbs in Key West

Last Updated on February 13, 2021

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, Florida Airbnb stays to help you make the most of your 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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Best Key West Airbnb - Airbnb Key West Fl - Airbnbs in Key West

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.
  • 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.

Pin these Key West Airbnb tips for later!


In this Key West Airbnb Guide:

Key West Airbnbs for Couples & Solo | Key West Airbnbs for 4-6 guests | Airbnbs for 6+ guests | Unique Key West Airbnb Stays


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.

The Galleria: Key West Studio with Shared Pool

2 guests · 1 bed · 1 bath · Kitchenette · WiFi · Cable · Shared pool

Airbnb Key West Florida - Leonardo Efficiency exterior
Images: Airbnb

This cozy studio has a kitchenette, queen bed, and shared pool access. With just enough space for 1-2 guests, this Key West Airbnb is located just blocks to the sights of Duval Street and Key West. There are several studios here, some of which are pet-friendly – check out more here if this one is booked for your stay.

Recent guest review: Loved this location close enough to Duval to be easy yet just far enough off to make parking and coming and going a breeze. The space is cozy but plenty for a couple. The bed was super comfy and the AC cold. Overall had a GREAT Thanksgiving night getaway!


Key West “Tiny House” Studio in Perfect Location

2 guests · 1 bed · 1 bath · Kitchenette · WiFi · Cable

Tiny House Studio - Key West Airbnb
Images: Airbnb

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!).

Recent guest review: Great little spot in the heart of KW. Walking distance to anything you want to do (bars, brunch, southern most point, Truman Annexes, Key West Express terminal etc.). I would definitely look to book this place again if available next time I’m in Key West.


Airbnb Key West Honeymoon Hideaway with Private Spa

2 guests · Studio · 1 bed · 1 bath · Kitchenette · WiFi · Cable TV · Spa · Shared pool

Honeymoon Hideaway - Key West Airbnb

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.

Recent guest review: This is our 5th time in Key West and our 4th time staying in one of Naomi’s suites. We just love the atmosphere here and the staff is so kind and accommodating. The pool area is so serene and in an amazing location. We comment all the time how quiet it is and being right off Duval. As always, the suite is very clean with great burners, refrigerator, micro & dishwasher… I don’t know why anyone would stay anywhere else when visiting Key West!


1-Bedroom Key West Cottage in great location

3 guests · 1 bedroom · 1 bed · 1 bath · Kitchen · Wifi · Cable TV

1-bedroom Key West cottage - Airbnb
Images: Airbnb

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.

Recent guest review: You will not be disappointed. Everything you could want or need is within walking distance. The scooter and bicycle rentals is across the street. A CVS is also diagonally across the street. About a block down Duvall there is a bank and an ATM. Restaurants are everywhere. It is centrally located so you can go see the most southern point one day in one direction and the next day take advantage and go the opposite direction to Mallory Square and watch the sunset. We were able to walk and ride bicycles almost everywhere.I cannot wait to return hopefully soon.


Key West Poolside Studio Villa Steps from Duval Sreet

2 guests · 1 bedroom · 1 bed · 1 private bath · Full kitchen · Wifi · Cable TV · Shared pool

Poolside Studio Villa - Key West Airbnb
Images: Airbnb

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.

Recent guest review: Quintessential key west experience. Swaying palms, adorable villa, awesome porch to sip wine in the evening. Super close to all the great restaurants but very quiet. Great pool. Walking distance to everything. Amazing host and staff. We could not have had a better time.


If you want to see more of the Florida Keys, consider a road trip from Miami to Key West! Get my ultimate Keys road trip planner and itinerary!

Miami to Key West Road Trip: Florida Keys Itinerary + Stops!

Taking a Miami to Key West road trip is a classic U.S. adventure. Get ready for the open road with this ultimate Florida Keys itinerary planner including sights, stops, and hotels for your Miami to Key West drive!

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Where to stay in Key West - Airbnbs

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.

Sugarpoppy Cottage | Key West Airbnb With Pool

6 guests · 2 bedrooms · 2 beds · 2 baths · Kitchen · WiFi · Cable TV · Pool

Airbnb Key West Florida - Sugarpoppy cottage
Images: Airbnb

Punch up your winter mood and your Instagram feed with this cheery conch cottage! Located just off Duval, this Key West Airbnb has room for 6 to relax with with 2 bedrooms, a sleeper sofa, and two full baths. Add on a dreamy front porch, a private pool, a rooftop deck, and plenty of indoor/outdoor space to make this a top pick for your group!

This listing is new to Airbnb, but the superhost has over 550 other reviews.


Key West Suites Hotel: 3 bed studio on Duval Street

6 guests · Studio · 3 beds · 1 bath · WiFi · Cable TV

Key West Suites Hotel - Airbnb Key West
Images: Airbnb

This charming yet affordable studio apartment overlooks Duval Street! With 2 king beds and one queen sofa bed in the studio space, it accommodates 4-6. This Key West Airbnb gets rave reviews for its location and is great for a family with young children.

Recent guest review: I would 11/10 stay here again!! It was exactly what I was expecting. I knew coming in that key west is a very walkable place, but their place is essentially centrally located to pretty much everything you could want to do down there! I can’t thank you enough for providing such a beautiful space!


Casa Cristol: 3 bedrooms with shared pool

6 guests · 3 bedrooms · 3 beds · 3 baths · Kitchen · WiFi · Cable TV · Shared pool

Casa Cristol - Key West Airbnb rental
Images: Airbnb

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.

Recent guest review: The location of this house is perfect! We could walk everywhere, and it’s right next to the pool. Our three children liked having space to spread out, and we enjoyed relaxing at the air B&B almost as much as we enjoyed exploring the island. The master bedroom made me feel like I was staying in a tropical tree house, and I enjoyed reading my book on the balcony.


Fleming-O Cottage: 2 bedrooms with outdoor living space

6 guests · 2 bedrooms · 4 beds · 1 bath · Kitchen · WiFi · Cable TV · Gas grill

Fleming-O - Key West Airbnb
Images: Airbnb

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.

Recent guest review: This place was perfect for our family of 4! The location was spectacular – close but not too close to the main tourist area, near some amazing casual restaurants… The house was well laid out with thoughtful touches, and the outdoor shower was a hit as well! (And was well appreciated with 4 people coordinating showers). Have already told friends thinking of heading to Key West that they have to stay here!


Hidden Treasure Cabin: 2 bedrooms with shared pool

6 guests · 2 bedrooms · 3 beds · 2 baths · Kitchen · WiFi · Cable TV · Gas grill · Shared pool

Hidden Treasure Cottage - Key West house rental
Images: Airbnb

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.

Recent guest review: Beautiful cottage! Everything was pristine and quiet. It seems to be nestled in a local neighborhood as there was zero noise. There are two king beds and a pull out couch about the size of a queen… They even put a little binder of things to do, places to see, and restaurants to eat at. Location was perfect, about a 5 minute walk to Duval St. I would stay here again in a heartbeat.


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Looking for a long-term Key West Airbnb? Check out these stays for 28 days or more.


Airbnbs in Key West

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 bedroom Key West Airbnb with Private Pool

8 guests · 3 bedrooms · 3 beds · 2.5 baths · Kitchen · WiFi · Cable TV · Pool

Casa Loca - Airbnb Key West rentals
Images: Airbnb

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.

Recent guest review: This house was not only gorgeous, but so clean and spacious. Our group had a great time staying at Casa Loca and I will definitely be making recommendations to others to stay here while in Key West. Incredibly close to Duval Street and all the action! 10/10 would recommend!


5-Star Getaway: 4 bedrooms with private heated pool

8 guests · 4 bedrooms · 4 beds · 3.5 bath · Kitchen · WiFi · Cable TV · Pool

5-star Key West Cottage - Key West Airbnb rental
Images: Airbnb

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.

Recent guest review: Penny’s place was just perfect for our Key West visit. Within walking distance to just about everything and offered lots of room for 2 families to stay together.


Key West Hideaway: 4 bedrooms with shared pool

10 guests · 4 bedrooms · 4 beds · 4 baths · Kitchen · WiFi · Cable TV · Pool

Key West Hideaway - Airbnb Key West
Images: Airbnb

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.

Recent guest review: Everything was beautifully maintained and the staff was very attentive. We had a fabulous weekend here. Great space inside and outside. And when it was raining on Saturday, we woke up to 4 large umbrellas on the back porch so we could still go shopping on Duval!!


Casa Grande: 5 bedrooms with private pool

12 guests · 5 bedrooms · 6 beds · 5.5 baths · Kitchen · WiFi · Cable TV · Pool

Casa Grande - Key West Airbnb
Images: Airbnb

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.

Recent guest review: The place is a gem. The photos do not do it justice. It is expensive, but the location is amazing and the pool is stunning, heated as well. Beds are very comfortable and the place is stocked with all the tools you need to host your large group or family. The house is also on a small block that ends in a dead end off of Duval, which adds tons of privacy to the location, as no one but residents go down the road. If we have a large group go to the keys again, we absolutely will be staying at this house again!



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

2 guests · 1 bed · 1 bath

Tiki Suite - Key West Airbnb

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!

Airbnbs in Key West - Key West Airbnb

Ready to book your Key West, Florida trip?

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Dry Tortugas National Park: Day Trip, Snorkeling & Camping

Last Updated on February 13, 2021 Planning a trip to Key West? Be sure to include a visit to Dry …

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If you have more time, a Miami to Key West road trip is the best way to experience all the sights, quirky stops, and sunsets of the Florida Keys! Get my ultimate itinerary and planner here.

Miami to Key West Road Trip: Florida Keys Itinerary + Stops!

Taking a Miami to Key West road trip is a classic U.S. adventure. Get ready for the open road with this ultimate Florida Keys itinerary planner including sights, stops, and hotels for your Miami to Key West drive!

Read more


Pin these Key West Airbnb picks for later!


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Adrienne, The Haphazard Traveler

I used to be a hot travel mess, but I got better! I kept the name and now blog my best tips for culture and adventure travel from around the globe. Follow along for travel advice, destination info, and photography from faraway lands - and at home in Washington, D.C.

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