Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Middle Keys
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Florida
Florida
Europe
Europe
Canada
Canada
Caribbean
Caribbean
Italy
Italy
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Gift cards
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Amazing pools
Beachfront
Countryside
Amazing views
National parks
Trending
Chef's kitchens
Play
Lake
Rooms
Camping
Tiny homes
New
Cabins
Houseboats
Boats
Bed & breakfasts
Design
Vineyards
Lakefront
Surfing
Golfing
Farms
Beach
Filters
0
Display total before taxes
Show map
Search results; Over 1,000 places
Over 1,000 places
Home in Key West
Suncoast House by Brightwild | Pool & Boat Dock
4 min drive
4 min drive
Apr 28 – May 3
Apr 28 – May 3
$1,353
night
$1,353 per night
New place to stay
New
Home in Key West
Casa Cristol - Family Friendly Classic KW Charm
18 min drive
18 min drive
Jul 28 – Aug 2
Jul 28 – Aug 2
$755
night
$755 per night
4.83 out of 5 average rating, 311 reviews
4.83 (311)
Guest favorite
Guest favorite
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
16 min drive
16 min drive
May 26 – 31
May 26 – 31
$545
night
$545 per night
4.99 out of 5 average rating, 83 reviews
4.99 (83)
Guest favorite
Guest favorite
Apartment in Key West
At Mine | Lovely Suite steps from Duval Street
17 min drive
17 min drive
Apr 20 – 25
Apr 20 – 25
$341
$207
night
$207 per night, originally $341
4.93 out of 5 average rating, 1020 reviews
4.93 (1020)
Superhost
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Palm
32 min drive
32 min drive
May 26 – 31
May 26 – 31
$635
$508
night
$508 per night, originally $635
4.74 out of 5 average rating, 58 reviews
4.74 (58)
Guest favorite
Guest favorite
Guesthouse in Key West
Old Town - Room Opens to Pool and Garden
15 min drive
15 min drive
May 28 – Jun 2
May 28 – Jun 2
$319
night
$319 per night
4.93 out of 5 average rating, 526 reviews
4.93 (526)
Guest favorite
Guest favorite
Condo in Key West
Top Floor Pool View Suite with Rooftop Balcony
7 min drive
7 min drive
Apr 19 – 24
Apr 19 – 24
$432
night
$432 per night
4.93 out of 5 average rating, 14 reviews
4.93 (14)
Home in Key West
Key West Canal Front Home. 15 min to downtown
17 min drive
17 min drive
Jun 16 – 23
Jun 16 – 23
$200
night
$200 per night
Boat in Key West
Panoramic Private Yacht on the Ocean!
11 min drive
11 min drive
Apr 21 – 26
Apr 21 – 26
$199
night
$199 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Superhost
Superhost
Houseboat in Key West
Happys Houseboat
12 min drive
12 min drive
May 25 – 30
May 25 – 30
$370
night
$370 per night
4.84 out of 5 average rating, 173 reviews
4.84 (173)
Superhost
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
35 min drive
35 min drive
Apr 28 – May 3
Apr 28 – May 3
$485
$427
night
$427 per night, originally $485
4.86 out of 5 average rating, 42 reviews
4.86 (42)
Superhost
Superhost
Apartment in Key West
The Perch on Duval- Hip & Modern Duval Suite
16 min drive
16 min drive
May 14 – 19
May 14 – 19
$602
night
$602 per night
New place to stay
New
Superhost
Superhost
Boat in Key West
Stay on the Roxie!
13 min drive
13 min drive
May 6 – 11
May 6 – 11
$242
night
$242 per night
4.89 out of 5 average rating, 85 reviews
4.89 (85)
Superhost
Superhost
Boat in Key West
The Escape- Private 2 Bed Rm Boat Beautiful Marina
9 min drive
9 min drive
May 6 – 11
May 6 – 11
$280
$211
night
$211 per night, originally $280
4.79 out of 5 average rating, 71 reviews
4.79 (71)
Superhost
Superhost
Cottage in Key West
Mango Cottage 2 bedroom 2 bath with private pool
14 min drive
14 min drive
Aug 12 – 17
Aug 12 – 17
$454
night
$454 per night
4.95 out of 5 average rating, 84 reviews
4.95 (84)
Guest favorite
Guest favorite
Houseboat in Key West
Key West Outpost: eco-vacation
16 min drive
16 min drive
May 31 – Jun 5
May 31 – Jun 5
$400
night
$400 per night
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Guest favorite
Guest favorite
Apartment in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
18 min drive
18 min drive
Jun 14 – 19
Jun 14 – 19
$481
$392
night
$392 per night, originally $481
4.97 out of 5 average rating, 236 reviews
4.97 (236)
Guest favorite
Guest favorite
Boat in Key West
Cozy Houseboat “Wild One”
13 min drive
13 min drive
Apr 28 – May 3
Apr 28 – May 3
$232
night
$232 per night
5.0 out of 5 average rating, 68 reviews
5.0 (68)
1
2
3
4
…
15