12 Airbnb Vacation Rentals To Keep Your Spirits High In Key West, Florida - Updated 2021

airbnb Key West
Crystal
Crystal
Updated

Party on even after the sun sets here at Key West, where a drink is always welcome. Rent a boat and chill out by the calm seas, enjoy jamming to a local band performance, sample delicious seafood, or visit the lively Duval Street for some good old entertainment and go bar-hopping with your friends.

Stay in close proximity to all the action with these Airbnbs in Key West, Florida.

1. Lovely treetop studio off Duval Street (from 239 USD)

Ideally located just steps off Duval Street in the heart of old town Key West, this spacious studio occupies the entire second floor of a historic house. It is well-appointed with a plush queen-sized bed, a fully stocked kitchen, as well as a sitting area that comprises a leather sofa and a tiny coffee table. Although there are restaurants just within walking distance of the studio, the kitchen is still fully equipped with a refrigerator, a coffee maker, a microwave, a dishwasher, and an oven, if you wish to prepare your own meals. Enjoy cocktails or stargaze on the secluded second-story deck that consists of a relaxing outdoor hot tub and a small sitting area covered by a parasol. The hosts go out of their way to make sure that you have the most wonderful vacation in Key West, so much so that they allow you to bring your pets into the house, though additional fees would apply.

Lovely treetop studio off Duval Street

Price: from 239 USD

Number of Guests: 4

2. Cozy studio just steps off of Duval Street (from 214 USD)

Located just steps off of Duval Street is a perfect spot for a stay in Key West! This recently renovated suite is well-appointed with a plush king bed with floral bedding, a private bath with a spacious two-person shower, as well as a small refrigerator and a microwave for you to prepare your own meals. You will have a bathroom all to yourself, and it is fully furnished with a shower, a toilet, and basic toiletries for you to refresh yourself. If you’d prefer to have a relaxing soak in a bathtub, then head to the outdoor hot tub on the patio! Aside from the hot tub, the patio also boasts a lovely sitting area comprising of comfortable cushioned chairs and a small table. Savor the peace and quiet of the surroundings while lounging on the patio. It is the perfect spot for hosting your own happy hour!

Cozy studio just steps off of Duval Street

Price: from 214 USD

Number of Guests: 3

3. Private yacht near Mallory Square (from USD 527)

Set sail for the high seas in this private yacht owned by the friendly host, Danny. You can choose to sail off the grid and enjoy a vacation of your lifetime away from the bustling city or park yourselves near the comforts of mainland and its convenience. Equipped with a long sofa for you to lounge in the fully air-conditioned comfort, feel free to spend the lazy Saturday evenings with a good read. Be sure to stock up on your beer and groceries if you’re heading out - you can use the kitchen to whip up a tropical breakfast out in the sea, and dive into the pristine waters of Key West. Snorkeling, scuba diving and fishing - you name it! There’s so much here for you to see, and the captain of the ship will be more than willing to show you around. After a long day of touring the seas, head back to the main salon of the ship for a movie night snuggled up on the cozy sofa. Choose from the classic comedy series of Friends for a good laugh, or pop a horror movie on for a good, old-school scare. If you find yourself nodding off, head into the main sleeping cabin for two in this Airbnb yacht, where the interior is furnished with a lovely painting of the dawn of a new day for a refreshing start the next day.

ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun
127 reviews Superhost  Wifi Available
Boat 4 Beds 5 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the last two nights with the a/c on were a welcome reprieve from the heat of the day
sleeping was amazing with great bed and the cool sea breeze
yeah it was okay i guess :d---(be very understanding of the bathroom
beds were very comfortable
Cleanliness:
the bathroom is small but clean and tidy
the boat was clean and fully stocked with everything we needed including plenty of fresh towels and sheets
everything in the cabin is set up nicely clean and neat
she's clean yet classic and shows signs of past adventures which is cool
boat was clean as a whistle
Host:
danny was a great host
danny is a wonderful host
danny is a fantastic host
danny is a great and generous host
danny was a fantastic and kind host
Location:
this was the perfect location for our family vacation
Read more reviews

4. Fully furnished apartment with sunset views (from USD 239)

If your plans in Key West involve a lot of sightseeing and activities on the beach, opt for this fuss-free apartment near Stock Island. This two-bedroom rental can accommodate up to six guests and is perfect for travelers who are eager to hit the golf courts or spend some time lounging by the water. After a long day under the sun, come home to enjoy excellent sunset views on the balcony.

Balcony in Key West facing sunset
Key West, Florida, United States
150 reviews
Entire condominium (condo) 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
two bathrooms washer/dryer and all the comforts of home
beautiful view for morning breakfast & coffee on condo’s private terrace
nice to have ceiling fans and air conditioning worked really well
nice apartment with a beautiful view
the sleeping couch is very comfortable as well as the beds
Cleanliness:
very clean and i recommend
it was impeccably clean
super clean lots of extra towels nice selection of cookware and dishes
space was clean
safe parking clean and quite place
Host:
nice floorplan easy to work with host
margaret is an awesome host
and margaret was really responsive in responding to our questions
very friendly quickly answering host
margaret is a great and thoughtful host
Location:
nice quiet location near airport
beautiful sunset and great location
great location next to smathers beach
close to everything by bike or uber but far enough away to just relax
comfortable condo and excellent location
Read more reviews

5. Tropical home with a fenced yard and a private pool (from USD 172)

If you’re looking for more upscale cabins in Key West, this property will feel like your own private resort. The blue color palette, floor-to-ceiling French doors, and the outdoor loungers by the pool will encourage rest and relaxation. You can head out to explore Duval Street or stay indoors and enjoy the many amenities on-site. This vacation rental has a spacious living room, a fully equipped kitchen, and two bedrooms suitable for up to six guests. Fire up the grill and enjoy a barbeque by the pool with your friends or family. You’ll find that this home has everything you need for a great holiday in the Keys.

**BIRD of PARADISE** Elegant Home & Pool + LAST KEY SERVICES…
Superhost  Wifi Available
Entire residential home 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

6. Newly renovated property in the heart of the Cuban district (from USD 607)

Those looking for Key West vacation rentals for large groups should check out this property. Situated in the heart of the Cuban district, this luxurious home features five bedrooms, five baths, and a well-equipped kitchen, not to mention Wi-Fi access for uploading those gorgeous holiday snaps onto social media! The kitchen, though small, comes fully equipped with an induction cooktop, a hot water kettle, a sink, a french press for coffee, an under-counter fridge, a large toaster oven, and basically everything you would need to prepare a meal. As if those weren’t enough to entice the guests, the gated property also includes a common outdoor sitting area, which is furnished with beautiful pots of flowers and lush greenery. It’s the perfect spot to enjoy a cold drink while stargazing at night.

Big Blu - 5 bedroom, 4 bath in old town
Key West, Florida, United States
48 reviews Superhost  Wifi Available
Entire residential home 5 Beds 12 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
the rooms and furnishings gave off a great vibe
huge comfortable bed in a studio with lots of natural light
the room itself was air-conditioned on arrival and decorated very well
the place is comfortable clean and updated with stylish furniture decoration and amenities
the cuban coffee a couple doors down at the laundry mat is delicious
Cleanliness:
clean and spacious suites
shawn’s place was great very clean and stylish and the bikes were awesome to get around
the bed was comfortable and the apartment was well-appointed and spotless
super cozy and clean very nice location
studio blu was well decorated comfortable and clean
Host:
shawn was a wonderful host
he was a great host
shawn was an excellent host
shawn was a great host with good recommendations for key west
shawn is really helpful
Location:
it’s close to everything and the neighborhood is safe and quiet
the location was perfect for us for walking or biking to many main attractions
you can walk or bike to all of the main attractions key west has to offer
the blu suite is an ideal place to stay for any couple staying in key west
the most stunning room in an incredible location in old town
Read more reviews

7. Two-bedroom holiday home near Higgs Beach

Scouting Key West bungalow rentals for the summer? This property is perfect for a family planning on spending more than 30 days in the Keys. There’s enough space for your furry friend to tag along, too. Stay cool under the hot weather by swimming laps in the private pool or by taking a doze on the shaded chaise. This rental is the perfect place to enjoy long, lazy days for the perfect summer holiday.

Plant-filled home with private pool and great central location!
Key West, Florida, United States
Entire house 2 Beds 2 Bedrooms 1 Bathroom

8. Cozy condo near the beach and top attractions (from USD 180)

Perfect for couples, this second-floor condo unit is a little piece of paradise in the Caribbean-like district of Key West. Its sole bedroom is fitted with a queen bed with a luxury mattress to give you and your partner the best night’s sleep. The unit is complete with air conditioning and heating, cable TV and WiFi, laundry, and ironing facilities. You’ll also have access to the property’s heated pool, full kitchen, and balcony. When you stay at this Airbnb, you’ll only just a short walk away from outdoor and water activities like snorkeling, parasailing, and fishing, and from attractions like Florida Keys Eco-Discovery Center, The Ernest Hemingway Home and Museum, and Fort Zachary Taylor Historic State Park.

WALK TO BEACH, MALLORY SQ.10% DISCOUNT 11/27-12/24
Key West, Florida, United States
60 reviews Superhost  Wifi Available
Entire condominium (condo) 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
we had breakfast on the deck every morning and relaxed there every evening
:) ac worked great full size kitchen with plates cookware
the pool was wonderful for a quick dip on a hot day
this is a lovely little one bedroom apartment in the shipyard section of the truman annex
Cleanliness:
it was clean and comfortable
clean quiet and very happy with our stay
wendy has a clean and amazing place to stay
pool in complex is small but very clean
wendy's apartment was clean and welcoming
Host:
also wendy was a great host she responded very quickly with questions that i had
wendy always very responsive
wendy was great to communicate with and super helpful
wendy’s recommendation were very helpful for our trip
wendy was very kind and great with communication
Location:
the location is perfect
location an accommodations were perfect
it was a great location to walk to anything
great condo in a great location to dining shops and the beach
wonderful place in the heart of key west
Read more reviews

9. One-bedroom condominium close to Duval

This spacious one-bedroom unit is furnished with tropical themed furniture, such as colorful, floral pillows on the rattan sofa, a leaf-shaped ceiling fan, not to mention the wooden furniture that is found all around the house. The apartment comes with a spotless kitchen-cum-dining area, which is well-equipped with a refrigerator to store your food, as well as a kitchen island where you can enjoy your meal as you watch the TV mounted on the wall. Alternatively, you can dine outdoors on the lovely deck, under a blanket full of stars. After a dip in the hot tub or a swim in the heated pool, retire to a plush queen-sized bed that is sure to provide enough comfort for a good night’s rest. Should you wish to host additional guests, the sofa bed in the living room can be employed upon request.

Tropical Old Town Bungalow
Key West, Florida, United States
142 reviews
Entire condominium 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the couch and bed are comfortable
lovely spot the outdoor space - deck & pool were even better than we anticipated
the bed was comfortable and it was nice to have a good working ac
great place with nice amenities and clean kitchen
such a nice place very accurate description and a nice sized apartment
Cleanliness:
the place was super clean and nice
everything was clean comfortable and modern
clean nicely decorated great bed plenty of towels
peaceful clean and stylish
the house is clean and well decorated
Host:
tina is a great host
tina was also a great host
tina was a responsive easy-going helpful host
tina was awesome to work with as well and very accommodating to any requests
tina is an excellent host and her place is extremely nice
Location:
the location is great
great location to old town
great location very central and charming
great location but would definitely recommend bikes to get around
everything is walking distance but recommend bikes vs walking
Read more reviews

10. The green house on Caroline Street (from USD 195)

Living up to its name of a green house, this newly renovated Airbnb home in Caroline Street has been lauded as the best Airbnb in Key West. It boasts lush viridian shrubbery all around you, all while leaving your own privacy to you and a group of four. Step into your new home furnished with the colours of a woodland forest. With hues of bamboo green lining the walls of oaken shelves, you can fall asleep to the silhouette of the dense canopy right here in the comforts of your new home. Have you always wanted to sleep in late and enjoy a breakfast in bed? Live out that dream with the cushy sofa-bed that extends to a queen-sized sleeper! Cook up a fragrant plate of scrambled eggs, topped off with a serving of honey-drizzled sausages and switch on your favourite Netflix show for a perfect Sunday afternoon. Adorned with wall art of varying styles, take a short tour around the house and see how many pieces of art you can spot! Ranging from carved woodworks of renaissance figures to still photography of the ever-changing ocean view, you can admire the many masterpieces lying around the house. Head over to your bedroom infused with a touch of the ocean waves. The quaint pastel blue walls are reminiscent of sea views that are unique to Key West, and the solitary pieces of coloured bamboo pieces resemble the seaweeds that tickle your feet when you dive into the crystal-clear waters. Rest up on the spacious double bed after a sweltering day of suntanning. If you find yourself unable to sleep, head out to the lanai beside your bed for a whiff of the salt-tinged air to relax.

Key West - Sunset ❀ The Green House
Key West, Florida, United States
171 reviews  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
definitely ask them to provide a fan for the bedroom and bedding for the sofa bed
the a/c unit works wonderfully and the apartment layout is nice
the bed was very comfortable the shower pleasant and the coffee maker was first rate
the room is more spacious than we anticipated and the a/c is really good
we also appreciated all the toiletries in the bathroom - makes traveling so much easier
Cleanliness:
it's clean shiny and spotless
clean and comfortable apartment
kitchen clean and handy
overall a nice apartment that was fairly clean and well managed
very clean and has all you need
Host:
host was awesome and responsive
kalman is the perfect host
the host was awesome so helpful but still never really saw him
kata and kalman were accommodating and responsive
kalman is an excellent host and very responsive to any questions you may have
Location:
it is located in a great location and truly close to the main strip
the location was excellent
great location if you want to be close to old town
this is a great location close to duval street and walking distance to everything
wonderful location in the heart of key west
Read more reviews

11. Vintage studio in central Cuban district (from USD 292)

Located in the heart of the Cuban district, this fully furnished studio offers an appealing queen-size bed with comfortable, vintage bedding, as well as a simple lounge area, a laptop-friendly desk, and a well-equipped kitchen. This studio undoubtedly scores for its fantastic location, steps from arguably the best ‘con leche’ in Key West and minutes from everything on the island, but its vintage claw-foot soaking tub makes it another strong contender for couples or solo travelers looking for a relaxing stay. For a truly home from home experience, cook your own meals in the tiny but well-equipped kitchen that consists of an induction cooktop and a convection oven. Enjoy your meal in the dining area adjacent to the kitchen, and admire the views of the neighborhood from the window as you tuck into the food.

Studio Blu
Key West, Florida, United States
255 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
went to the coffee shop that was recommended & had an awesome breakfast to start the day also
you will enjoy this quaint private room in a quiet setting
found the space to be just as described and very comfortable
the studio is well prepared with a very cool kitchen and bed
ther could be more windows in the room but the mirror does a good job too
Cleanliness:
very clean and cozy
efficiency apartment was very clean and beautifully decorated
house was clean and well equipped
studio was clean and cozy
found the apartment to be very clean and comfortable
Host:
shawn is an excellent host
shawn was friendly and helpfull host
shawn was very helpful and quick to respond
shawn and romi were amazing hosts will definitely recommend to everyone
shawn was very thoughtful and responsive
Location:
a great location
great little spot close to everything
location is great with everything needed within walking distance and an easy bike ride to duval st
this is an ideal location for exploring key west
much better location than chain hotels can walk to everything
Read more reviews
Monthly discount: 10% off

12. Master suite near Atlantic Boulevard

Live like royalty here in this master suite featuring vaulted ceilings that bathe the entire house in soft, natural lighting. The hues of deep reds that colour the interior a rich burgundy make for a exquisite getaway after a long day of exploring. The huge king-sized bed doubles as a cushy couch during the day. Huddle up on the cushioned sofas with a light read on hand if you are unable to fall asleep - the moonlight shining down from the skylights make for a soothing nightlight. Wash away the fatigue of the day by soaking in the hot tub exorbitantly furnished with an ornate dressing table for your detailed skincare routine. Are the post beach withdrawal symptoms hitting you? Head out to the outdoor lounge area for a whiff of the sea breeze after the sun sets. Lit up with a crystal lamp, you don’t have to worry about bumping into tabletops or spilling your drink! Head out to the balcony for a morning stretch, or relax in the beach chairs under the shade of the neighbouring palm trees if you want a stay-home Saturday.

Master Suite along the Beaches
Key West, Florida, United States
7 reviews
Private room in guest suite 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Host:
beautiful property gracious hosts i would definitely recommend
Location:
the property location and attention to detail was perfect
higgs beach the best on the island is only a block and a half walk away
Read more reviews

The key is in your hands

Here’s your chance at creating a dream vacation just for you and your loved ones. Choose from these Airbnbs in Key West that are but steps away from the convenient tourist stops without busting your budget, while still having access to a high-quality living environment.

Frequently asked questions about Airbnbs in Key West, Florida

1. Which are the best Airbnbs for couples in Key West?

Couples holidaying in Key West will enjoy staying in this romantic guest suite complete with a covered skylight or this private apartment located just steps away from everything.

2. Which are the best budget-friendly Airbnbs in Key West?

The best of the Keys can still be enjoyed on a budget. This fully furnished apartment not only offers a comfortable place to stay but it comes with a balcony where you can enjoy incredible sunset views.

3. Which are the best pet-friendly Airbnbs in Key West?

If you’re traveling with pets, check out this holiday home for four. This dog-friendly rental lets you enjoy a laid-back holiday with your whole family.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Crystal is a curious child, who loves exploring Singapore in her free time with a camera in hand. Her street photography subjects often include unaware strangers, uncommon architecture, and...Read more

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