Best Airbnbs in Key West: 21 Dreamy Old Town Stays in Florida’s Conch Republic

If you’re heading to Key West soon — the Southernmost Point in the USA and the Conch Republic — we’ve got the coolest Airbnbs in Key West you absolutely have to stay in!

It’s no wonder Key West is still such a hot place to visit after all these years. Where else can you find great weather year round, adorable conch houses surrounded by towering palms trees that sway in the tropical trade winds, and the lively atmosphere that’s everywhere in Key West?

Key West is an absolutely gem — one for your Florida bucket list for sure. There’s always a party going on, yet it’s one of most laid-back resort towns in Florida.


>>> Is this your first trip to Key West? Read our First Timer’s Guide to Key West before you go!


But given its vacation reputation and despite its small size, there are a ton of places to stay in Key West. It can be confusing to find just the right place for your tropical island vibe. Where should you stay? Where exactly is Old Town or New Town? Should you choose a hotel or quaint B&B? Can you have all the charm and the great location at a good value? Yes you can!


Our choice? Stay in one of these super-cool and oh-so-dreamy Airbnbs in Key West!


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OVERALL Most Unique & Best Airbnbs in Key West

The Best Overall AirBNB in Key West, Florida – Pilar’s Secret

The Best Luxury AirBNB in Key West, Florida – Casa Margarita

The Best Key West, Florida AirBNB For Groups – Big Blu Key West Airbnb

The Best Unique AirBNB in Key West, Florida – The Luxury Boat Experience Aboard Wanderland

Where to Stay in a Key West Airbnb?




Old Town vs. New Town


Many of Key West’s historic buildings grew up around Duval Street which runs north-south on the western part of the island from Mallory Square in the north to the Southernmost Point in the south.

At one time the small bungalows in Old Town — called Conch houses — were everything from cigar houses used for storing tobacco leaves to horse and livery stables. You’ll also find grand old Victorian homes too, many of which are luxury hotels or condos today.

Old Town Key West is the best place to stay for charming and historic architecture. It’s the part of town you want to be in for the most authentic Key West feel!


But I Want to Stay Near the Beach


Of course you do! If you’ve never been to Key West before, it may be hard to imagine what to expect. Key West is the southernmost point in the USA (90 miles from Cuba) and the last of the Florida Keys — the chain of mangroves that stretches from Miami south by southwest around Florida Bay.

And while south Florida may be known for beautiful beaches in Naples and Miami, that’s not generally the case in the Keys. Until recently, there were really no beaches in Key West to speak of.

But today, thanks to the ever changing winds, tides, more than its share of hurricanes, and increased funding, Key West has a couple of beaches that are perfect for family vacations and the most romantic getaways you can imagine.

If you’re looking for a beach vacation, Key West has two nice beaches at Higgs Beach and Smathers Beach. But they are not in Old Town. However, there are great little Key West airbnbs at the beach for you beach-lovers too.

  • Higgs Beach is .08 miles from Old Town

  • Smathers Beach is over 2 miles (2.2) from Old Town

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Best Airbnbs in Key West for Long Term Stays


If you’re planning on slow traveling Key West or have more time to spend exploring — like a month or longer — we found some incredible deals in the heart of Old Town, like this adorable cottage with a divine pool to laze the day away. Scroll down to find some of our favorite long-term Key West Airbnb rentals, close to everything including Key West attractions and beaches.



This post may contain affiliate links which means we may earn a commission at no extra cost to you should you click and make a purchase. As an Airbnb Associate, we earn when you book through this link.





21 Best Airbnbs in Key West

 

1. Classic Key West cottage featuring shared pool, courtyard, covered front porch


This cottage offers all the comforts of home in a quiet neighborhood. Duval street where you'll find great restaurants, and popular night spots is just a block away. The high-end kitchen, modern amenities, shared swimming pool and sundeck, and tropical courtyard make this a great place to stay in Key West.

https://www.airbnb.com/rooms/21615672

Location: Whitehead St. (1 Block from Duval, close to Southernmost Point)

Accommodations: Entire condominium, 2BR/6 guests

Superhost: No

Price: $366

Guest Reviews: “This place was perfect for us–loved the private feeling of the garden. We didn't mind sharing the pool with our neighbors at all, in fact, we really enjoyed visiting with them and running into them around Key West. All in all, Papa's Hideaway was exactly what we needed for our 5 days in Key West. We would definitely stay here again.” — Ben

View Photos, Read Reviews & Check Availability


 
 
 

Perfect for Couples and Small Families
 

2. Malaga Room in Andrews Inn

This amazing location in Andrews Inn is adjacent to the Hemingway Estate. The Malaga Room features a private bathroom and terrace and is ideal for three guests. Bottomless mimosas served with a great breakfast, free afternoon happy hour, daily housekeeping, and limited free parking are all included in the rate.

https://www.airbnb.com/rooms/24350434

Location: Old Town (between Duval and Whitehead)

Accommodations: Queen room w/sleeper sofa and private deck

Superhost: Yes

Price: $144+

Guest Reviews: “This place is absolutely PERFECT. Whether it’s price, location, amenities, hospitality or the overall aesthetic, Michale’s place is everything we could have imagined and then some. I would highly recommend this space to a couple, small family for your trip to Key West. The location was close to both north and south Duval St. Attractions, but was extremely quiet at night and felt secluded from the chaos. The space is quirky, fun and gives off the real Key West vibe.” — Steven

View Photos, Read Reviews & Check Availability


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Our favorite place for groups and extended families!
 

3. Big Blu Tropical Home in Old Town



This spacious tropical 5BR/5BA home reminds us of Bali, and it’s absolutely GORgeous! Big Blu is a unique property situated on the island with the beach just a few blocks away, and Cuban coffee shops steps from the house. Relax in the large heated pool with jacuzzi jets and prepare meals in the state of the art kitchen.

https://www.airbnb.com/rooms/22858198

Location: New Town (White Street, south of Truman)

Accommodations: Entire home, 5BR/12 guests

Superhost: Yes

Price: $700+

Guest Reviews: “Shawn’s place is beautiful! It is exactly as it appears in the photos. The skylight is a great bonus! The bikes are also a great amenity, we didn’t drive our car the entire weekend. It is the perfect space for an island getaway!” — Abby

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4. Spacious, Truman Annex Waterfront Condo w/ a full kitchen, shared pool, & furnished balcony


Located in the Truman Annex, this spectacular condo features beautiful water views with a view of Key West harbor from a private furnished balcony. The property has a full gourmet kitchen for easy meal preparation and plenty of seating for dining. Guests also enjoy access to the on-site pool. If you’re looking for a gorg condo on the beach a la Naples or Siesta Key, this just might be the perfect place for you!

https://www.airbnb.com/rooms/42998868

Location: Prime Old Town (Truman Annex)

Accommodations: Entire condominium 2BR/6 guests

Superhost: No

Price: $500+

Guest Reviews: Only one review so far — it’s that new! But Lamar thought it was a “Great place!” If you’re looking for a fabulous Airbnb in paradise, this place is about as perfect as you can get.

View Photos, Read Reviews & Check Availability


 
 
 

5. Duval Street Duplex w/ Balcony and Parking

This private two story duplex features a balcony right on Duval Street. It's a great location in the heart of Old Town and within easy walking distance of restaurants, bars, shops, and live music.

Guests have a private entrance along with access to the pool and grounds. Daily complimentary breakfast is included. There’s also FREE PARKING on premises which is rare in Key West, but perfect if you’re on a Florida road trip heading down A1A from Miami!

https://www.airbnb.com/rooms/22302593

Location: Old Town (between Duval and Whitehead)

Accommodations: Entire apartment 2BR/up to 8 guests

Superhost: Yes

Price: $250+

Guest Reviews: “We all had a wonderful and safe time at the Duval House overlooking historic and famous Duval St. The staff are accommodating and quickly responsive. Even (now), we felt safe and attended to. We would definitely stay here again!” — Michael

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Our Pick for the OVERALL Best Airbnb in Key West!
 

6. Pilar’s Secret - An Oasis right off Duval


Named for Ernest Hemingway`s famed fishing boat, this gem of a vacation home located just a half block from Duval Street is quintessential Key West. There's luxury throughout with three spacious bedrooms, a private pool and gated outdoor area, a fully equipped kitchen and a large living space.

But even though it’s a half a block off Duval, its location on a quiet lane gives you the best of both worlds. It’s the reason we named it The Best Overall Airbnb in Key West, Florida!

https://www.airbnb.com/rooms/31670156

Location: Old Town (between Simonton and Duval)

Accommodations: Entire house, 3BR/8 guests

Superhost: Yes

Price: $300+

Guest Reviews: “Beautiful hideaway yet close to everything! We took my daughter and a few friends down for her 21st birthday and couldn’t have picked a more perfect place to stay! Beautiful home, super clean and plenty of room for the six of us. We had activities planned but also loved just hanging out by the pool.” — Jill

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7. Contemporary Dog-friendly Cottage


This dog-friendly cottage enjoys a prime central location near the beach and lower Duval Street and has access to a shared pool. Whether you like to wander through shops, enjoy an afternoon beverage, dine at an excellent restaurant, or just pass the time with a good book on the beach, this dog-friendly home makes your visit easy to enjoy.

https://www.airbnb.com/rooms/21617153

Location: Old Town (between Simonton and Duval)

Accommodations: Entire condominium, 1BR/4 guests

Superhost: No

Price: $300+

Guest Reviews: “The perfect place ! Don’t hesitate!” — Audrey

View Photos, Read Reviews & Check Availability


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8. Casa Margarita in Old Town


In the heart of Old Town near the Historic Seaport, this is the perfect luxury home if you are looking for a peaceful retreat. The three-bedroom, three-bath home features a large backyard with tropical landscaping, a heated pool, covered patio, and a large hot tub with a capacity of up to six people.

There's even an outdoor flat-screen TV. Casa Margarita is ideal for outdoor dining and relaxing.

https://www.airbnb.com/rooms/31640915

Location: Perfect Old Town location, 1 block from Key West Bight off Caroline Street

Accommodations: Entire house, 3BR/8 guests

Superhost: Yes

Price: $700

Guest Reviews: “Amazing stay at Casa Margarita! The house is in a great location right by the harbor. Easy access to so many fun bars and restaurants and only a few block walk (easy) to the fun of Duval street. The house itself is cozy, comfortable and had everything you need to enjoy your stay. Everyone raved on how comfortable the beds are. The outside space is AMAZING! It makes your stay. So much fun to come home and jump in the pool and relax! This is a must stay home! — Melissa

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9. Old Town Studio Apartment

Walk everywhere from this prime location! Live like a local in this great Key West neighborhood. Walk to Cuban coffee shops, an organic market, and excellent restaurants. Or just relax on the front porch with your favorite beverage. You can either walk everywhere or take the Duval Loop bus to get around.

https://www.airbnb.com/rooms/28935962

Location: Old Town (Eaton and Frances Streets)

Accommodations: Entire apartment, 1BR/2 guests

Superhost: Yes

Price: $90+

Guest Reviews: “The location couldn't be any better. There's a grocery store down the street and you're only a few blocks away from Duval St. I had a great time at Julie's place, everything was as described if not better!” — Luka

View Photos, Read Reviews & Check Availability


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10. Oasis in Key West with private heated pool!

This is a classic compact Key West 'Conch' house. Located in a quiet residential neighborhood in Old Town just a few blocks to Duval Street, the house is perfect for dining, shopping, and nightlife. It has a fabulous patio with a dining table, lounge chairs, and a new outdoor shower. All you need to bring is your bathing suit, a pair of shorts, and flip flops.

https://www.airbnb.com/rooms/24493509

Location: Old Town (Olivia Street near Elizabeth)

Accommodations: Entire cottage, 4BR/8 guests

Superhost: Yes

Price: $120+

Guest Reviews: “Great place to stay! Lots of nice cafes and places to get food nearby. The location is also great to walk around town and get to Duval St. There is no private parking, which was a little tricky with our baby, but this is also very common for Key West, but overall it was a great place and we would stay there again! Irene was super helpful and very responsive with my messages!” — Chelsea

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11. Wanderland, A 50’ Luxury Yacht Experience



This is a luxury boating experience. Wanderland is anchored 1.7 miles off of Key West, in tranquil waters. Wanderland is a 50-foot yacht with big open rooms that can sleep up to 10. Anchored 1.5 miles off Key West you'll have an unobstructed view of Key West's famous sunsets.

She has full bathrooms with showers, a refrigerator, air conditioning, a microwave, gas grill, kayaks and paddle boards.

Getting back and forth is via two daily one-way shuttles from boat to land and land to boat. Schedule during the stated hours and we pay for you shuttle runs.

https://www.airbnb.com/rooms/43777587

Location: Off Old Town Key West

Accommodations: Private Boat, 3BR/10 guests

Superhost: No

Price: $250+

Guest Reviews: “Our stay on the Wanderland was incredible! Robert and Angel provided us such a unique experience that we’ll remember for a while. the boat is parked in a very secluded and quiet corner of key west and was perfect for our trip. i would definitely recommend this for people who are less picky about traditional amenities (water, AC etc) because it’s fun to live off the grid for a few days.

The outside of the boat is much more comfortable to sleep in during the summer than the bedrooms, but no complaints. the views were insane! We were even given a sunset trip out to a sand bar. definitely a fantastic trip for young people looking to just hang out for a bit and disconnect.” — Lindsey

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12. The Bartlum Studio

This studio apartment with a full kitchen is attached to a grand historic conch home and enjoys private access through a street-front courtyard. Duval Street is less than a block away making for a short walk to shops, restaurants, bars, and more.

https://www.airbnb.com/rooms/30979059

Location: Old Town (Simonton and Caroline Street)

Accommodations: Entire apartment, 1BR/4 guests

Superhost: Yes

Price: $175

Guest Reviews: “Great location! Beautiful neighborhood and the place is clean, modern and accurate to photos and description. Beautiful gem in Key West!” — Maria

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13. Beautiful King Room in Andrews Inn

Part of the Andrews Inn adjacent to the Hemingway Estate, this beautifully decorated room has a private bathroom, a king-size bed, and in-room refrigerator. Enjoy a great breakfast with bottomless mimosas, free afternoon happy hour, daily housekeeping, and limited free parking all included in the rate. Amazing location in the heart of Old Town Key West!

https://www.airbnb.com/rooms/34747976

Location: Old Town (Duval at Truman Street)

Accommodations: Private King room in bed and breakfast, 1BR/2 guests

Superhost: Yes

Price: $150+

Guest Reviews: “Beautiful inn! It felt like home. The bed was so comfy, breakfast was delicious, happy hour was fun, the pool and private garden were relaxing, and the host are about the most wonderful people you will ever meet. A couple of my favorite parts of my stay were looking out my window and watching the Hemingway cats lounge by the pool and the water and ice machine. It was so nice to come back during the day for a quick cool down and to rehydrate.” — Danielle

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14. The Galleria Coral Cove

Coral Cove is perfectly located just steps away from Duval Street with its shops, restaurants, bars, and more. Relax and enjoy the many shared common spaces around the propert as well as the shared pool.

https://www.airbnb.com/rooms/44374124

Location: End of Duval near Southernmost Point

Accommodations: Entire loft, 1BR/2 guests

Superhost: Yes

Price: $131

Guest Reviews: “Amazing location! Just a short walk from Duval street and all the action. Place was clean and offered everything we needed including a pool. Highly recommend if your staying in Key West.” — Daniel

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15. Atlantic Ocean and Higg’s Beach Studio

This studio is in a small ocean front time share resort with its own private beach, heated pool, and hot tub. In the studio there is a king size bed, a small fridge, microwave and utensils - enough for two people. And it's only a 5 minutes walk to Duval Street.

https://www.airbnb.com/rooms/32464336

Location: Perfect Beach location near Higgs Beach

Accommodations: Entire condominium, 1BR/2 guests

Superhost: Yes

Price: $195

Guest Reviews: “This is a studio in a great little private time share. Great value. Heated pool, hot tub, a small private beach, guest laundry, and a bar although it was closed during my stay. Friendly people and great staff. Very close to Duval street.” — Jeffrey

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16. Perfect Old Town Key West Historic House

The Banyan Resort, surrounded by lush gardens and majestic Banyan trees, is just two blocks from Mallory Square and the nightly sunset celebration, and just one block from Duval Street. The resort includes two temperature controlled swimming pools along with a relaxing hot tub.

https://www.airbnb.com/rooms/32285058

Location: Perfect Old Town location, 2 blocks from Mallory Square

Accommodations: Entire condominium, 1BR/4 guests

Superhost: Yes

Price: $150

Guest Reviews: “Fantastic location, walking distance to anything you could want or need.” — Kristin

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Best Airbnbs in Key West for Slow Travelers and Long-Term Stays



Planning on spending some time in Key West? If you love slow travel like we do, spending more time in Key West and Florida Keys is a great idea. There is so much to explore on land and in the water, and spending a month or more would not be hard to do. Plus, staying longer allows you to get to know the locals much more so than a quick tropical vacay, and eat your way through the Keys (the food in Florida — and south Florida — is divine!).

The perks to a long-term stay are many, including these amazing properties to rent in the heart of Old Town. What could be better than staying at some of the best Airbnbs in Key West for a month or longer?


 

17. 19th Century Conch House


Location, location, location! This lovely 19th century Conch house with a large private deck is in the heart of the Old Town Seaport area. Walk one block to the Historic Seaport Harbor filled with ocean front bars/restaurants, sunset cruises, and Dante’s famous pool bar. It's an easy four block walk to Duval Street.

https://www.airbnb.com/rooms/39885197

Location: Old Town (between Eaton and Fleming)

Accommodations: Entire apartment, 1BR/4 guests

Superhost: No

Price: $90

Guest Reviews: “Great apartment just steps from the historic seaport. On a quiet street yet right in the middle of the action. The apartment is totally renovated and tastefully decorated. It has a large deck with comfy lounge furniture. The kitchen is fully stocked. The bed is comfortable, and the bedroom nice and dark. Overall, a terrific find!” — Albena

View Photos, Read Reviews & Check Availability


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18. Open Floor Plan Cottage w/private deck and swimming pool

This Old Town cottage features an open floor plan with doors that open to the back patio to create indoor/outdoor living. Just steps from Duval Street for dining and shopping, and an easy walk to the Hemingway House, the Harry Truman Little White House and more. When done with the day's adventures cool off in your own private plunge pool.

https://www.airbnb.com/rooms/43592715

Location: Old Town (South of Truman, Half Block Off Duval)

Accommodations: Entire condominium, 2 BR/6 guests

Superhost: No

Price: $180+

No Guest Reviews Yet — this listing is Brand New! But it’s managed by a local company with other Key West properties that always get high marks. Check it out!

View Photos, Read Reviews & Check Availability

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19. The Maloney Luxury Penthouse

Originally built in 1908 as the first pharmacy in Key West, The Maloney is a 2,000+ square foot luxury penthouse which encompasses the entire second story of the historic red brick building. It's the perfect setting to host a quiet dinner or serve cocktails to friends.

https://www.airbnb.com/rooms/26916056

Location: Old Town on Simonton Street

Accommodations: Entire condominium, 2 BR/6 guests

Superhost: Yes

Price: $400

Guest Reviews: “This apartment is exactly as shown in the pictures--modern, clean, and minimalist. The many windows provide lots of natural light and great people-watching. We look forward to staying here again in the future.” — Mike

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20. Prime Old Town location w/ private parking & great porch!

This home is situated on a hidden lane in the heart of Old Town only one block from Duval Street and features a spacious wrap-around porch and private parking. You'll be within walking or biking distance of shops, bars, restaurants, and Key West's most popular attractions.

https://www.airbnb.com/rooms/41770593

Location: Thomas Street in Old Town

Accommodations: Entire house, 2 BR/6 guests

Superhost: No

Price: $130+

Guest Reviews: No reviews yet — this listing is brand new!

View Photos, Read Reviews & Check Availability

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21. Dog-friendly home in Old Town


Now you can enjoy all that Key West has to offer and bring your best friend too! The location of this home is terrific, and the home features a full kitchen, clawfoot bathtub, front porch, and plenty of Key West charm. Walk or bike to popular destinations such as Higgs Beach, Mallory Square, and Margaritaville.

https://www.airbnb.com/rooms/30071376

Location: Thomas Street in Old Town

Accommodations: Entire house, 1 BR/4 guests

Superhost: No

Price: $140+

Guest Reviews: “Great location! All the comforts of home, and walking distance to everything.” — Peter

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Thanks for checking out our Airbnb Key West Guide!

Need some ideas for Key West tours? Here are some of our favorite tours in Key West, from the absolute must-do Sunset Catamaran Cruise to flying high over Old Town in a tandem parasail!




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KEY WEST TOURS to Book for Fun

Key West: Sunset Party Cruise by Catamaran

This sunset tour is top-rated on Get Your Guide, and we’ve taken this so many times. It’s always one of our favorite things to do in Key West! Check more info and availability.



Go Parasailing in Key West

This is such a cool way to get a bird’s eye view over Key West — and the surrounding azure water. It’s such a fun thing to do, and you can even go up with a few friends — all on the same flight! Check here for more details and availability.


Drag Queen Guided Pub Crawl with Sing-a-longs!

You’re in Key West, and we can’t think of a better way to experience the fun and wildly raucous flavor of this town — on a multi-colored Duval Crawl escorted by a Queen. Fabulous fun! Check here for details and to reserve your space! This one sells out quickly! ;-)


What amazing Airbnb Key West vacation rental are we missing? Do you love staying in local Airbnbs in Key West or prefer luxury resort hotels?

If you are a Key West Airbnb host and would like to see your property featured on this list. Let us know! We’d love to consider you for our next update of Airbnbs in Key West.


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