Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Sugarloaf Key
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Navigate forward to access suggested results
Search by region
I’m flexible
I’m flexible
Florida
Florida
Europe
Europe
Italy
Italy
Caribbean
Caribbean
France
France
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Airbnb your home
Help
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Rooms
Amazing pools
Beachfront
Amazing views
National parks
Trending
New
Play
Camping
Cabins
Houseboats
Chef's kitchens
Tiny homes
Boats
Bed & breakfasts
Design
Lake
Farms
Beach
Surfing
Golfing
Filters
0
Show map
Search results
Over 1,000 places
Display total price
Includes all fees, before taxes
Home in Sugarloaf Key
Palms Resort at Sugarloaf Beach - Green House
7 beds
Jun 26 – Jul 1
$935
$756
night
$756 per night, originally $935
4.78 (72)
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
2 sofa beds
Jun 1 – 8
$1,135
night
$1,135 per night
4.87 (15)
Home in Sugarloaf Key
Palms Resort at Sugarloaf Beach - Grey House
7 beds
Jun 10 – 15
$1,810
$1,373
night
$1,373 per night, originally $1,810
4.72 (71)
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Hemingway
3 beds
Jun 24 – 29
$715
$501
night
$501 per night, originally $715
4.68 (25)
Home in Key West
Sunset Harmony Key West
2 beds
Jun 29 – Jul 4
$321
night
$321 per night
New
Home in Summerland Key
Fabulous entertainment home
4 beds
Jun 4 – 9
$595
night
$595 per night
New
Apartment in Key West
At Mine | Lovely Suite steps from Duval Street
1 bed
Jun 5 – 10
$312
$171
night
$171 per night, originally $312
4.95 (571)
Home in Cudjoe Key
NEW! 2BR,2BA Waterfront UPDATED w 35' Seawall! WOW
3 beds
Jul 29 – Aug 5
$537
$399
night
$399 per night, originally $537
4.86 (36)
Superhost
Camper/RV in Big Pine Key
Beautiful private camper situated amongst nature
1 queen bed
Jun 19 – 24
$125
night
$125 per night
4.85 (320)
Superhost
Home in Cudjoe Key
Newly Renovated Oceanside House with Pool
2 king beds
Jun 19 – 24
$315
night
$315 per night
4.89 (151)
Superhost
Apartment in Key West
Beautiful King Bedroom + Pools & Free Shuttle
1 king bed
Jun 1 – 8
$210
$161
night
$161 per night, originally $210
4.53 (19)
Home in Cudjoe Key
Private Ocean Oasis by Key West, Florida
4 beds
Jun 1 – 7
$325
night
$325 per night
5.0 (4)
Superhost
Home in Cudjoe Key
Sea Haven - Waterfront "Venture Out" Home w/ Dock!
2 king beds
Jun 11 – 16
$437
$383
night
$383 per night, originally $437
4.94 (33)
Home in Key West
The Blue Water Bungalow: canal front home + dock
5 beds
Jun 3 – 8
$449
night
$449 per night
Home in Summerland Key
Luxurious 4BR Oceanfront | Pool | Balcony
4 beds
Jun 2 – 7
$2,165
night
$2,165 per night
4.33 (6)
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
7 beds
Sep 17 – 22
$681
night
$681 per night
4.97 (35)
Superhost
Home in Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
3 beds
Aug 12 – 17
$329
night
$329 per night
4.82 (183)
Superhost
Home in Cudjoe Key
Sunrise Beach Escape
2 beds
Jun 1 – 8
$350
night
$350 per night
4.9 (92)
Superhost
1
2
3
4
…
15
