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
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
Superhost
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
1 sofa bed
1 sofa bed
May 19 – 24
May 19 – 24
$680
$544
night
$544 per night, originally $680
4.87 out of 5 average rating, 45 reviews
4.87 (45)
Superhost
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Hemingway
3 beds
3 beds
Apr 29 – May 4
Apr 29 – May 4
$839
$622
night
$622 per night, originally $839
4.86 out of 5 average rating, 63 reviews
4.86 (63)
Superhost
Superhost
Home in Sugarloaf Key
Bungalows at Sugarloaf Beach - Mi Azucar
7 beds
7 beds
Apr 28 – May 3
Apr 28 – May 3
$1,191
$774
night
$774 per night, originally $1,191
4.75 out of 5 average rating, 111 reviews
4.75 (111)
Home in Lower Sugarloaf Key
Sunsets & Seclusion
Nov 18 – 25
Nov 18 – 25
$420
night
$420 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Home in Key West
Waterfront Key West House w/Dock
6 beds
6 beds
May 8 – 14
May 8 – 14
$296
night
$296 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Superhost
Superhost
Home in Sugarloaf Key
Palms Resort at Sugarloaf Beach - Main House
7 beds
7 beds
Apr 29 – May 4
Apr 29 – May 4
$1,655
$1,256
night
$1,256 per night, originally $1,655
4.73 out of 5 average rating, 83 reviews
4.73 (83)
Superhost
Superhost
Home in Summerland Key
Bungalows at Sugarloaf Beach - Little Hammock
1 bed
1 bed
May 2 – 7
May 2 – 7
$495
night
$495 per night
4.83 out of 5 average rating, 6 reviews
4.83 (6)
Superhost
Superhost
Home in Sugarloaf Key
Bungalows at Sugarloaf Beach - Hammock House
4 beds
4 beds
May 2 – 7
May 2 – 7
$1,574
night
$1,574 per night
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Superhost
Superhost
Home in Cudjoe Key
Newly Renovated Oceanside House with Pool
2 king beds
2 king beds
May 21 – 26
May 21 – 26
$269
night
$269 per night
4.88 out of 5 average rating, 188 reviews
4.88 (188)
Superhost
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
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)
Home in Summerland Key
Pelico Palms Sunset Cottage
4 beds
4 beds
Apr 19 – 24
Apr 19 – 24
$335
night
$335 per night
4.91 out of 5 average rating, 23 reviews
4.91 (23)
Guest favorite
Guest favorite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Kayak
Kayak
Boat slip
,
·
Boat slip
Ocean views
,
·
Ocean views
Jul 17 – 22
Jul 17 – 22
$439
night
$439 per night
4.91 out of 5 average rating, 77 reviews
4.91 (77)
Guest favorite
Guest favorite
Home in Cudjoe Key
White Vacation Home. Free cancellation see details
5 beds
5 beds
Sep 21 – 28
Sep 21 – 28
$410
night
$410 per night
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Guest favorite
Guest favorite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
4 beds
4 beds
May 26 – 31
May 26 – 31
$514
night
$514 per night
4.91 out of 5 average rating, 145 reviews
4.91 (145)
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
6 beds
6 beds
May 18 – 23
May 18 – 23
$512
night
$512 per night
4.78 out of 5 average rating, 73 reviews
4.78 (73)
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 beds
4 beds
Apr 29 – May 4
Apr 29 – May 4
$1,500
night
$1,500 per night
4.45 out of 5 average rating, 11 reviews
4.45 (11)
Home in Summerland Key
Pelico Palm Villa
5 beds
5 beds
Apr 22 – 27
Apr 22 – 27
$804
night
$804 per night
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Superhost
Superhost
Cottage in Cudjoe Key
OCEANIA... water front cottage retreat ~
3 beds
3 beds
Apr 29 – May 4
Apr 29 – May 4
$821
$371
night
$371 per night, originally $821
4.83 out of 5 average rating, 84 reviews
4.83 (84)
1
2
3
4
…
15