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Sugarloaf Key
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Search results; Over 1,000 places
Over 1,000 places
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 - 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 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 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 Key West
Waterfront Key West House w/Dock
6 beds
6 beds
May 8 – 14
May 8 – 14
$301
night
$301 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
4.8 out of 5 average rating, 5 reviews
4.8 (5)
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
Apartment in Key West
At Mine | Lovely Suite steps from Duval Street
1 queen bed
1 queen bed
Apr 20 – 25
Apr 20 – 25
$341
$194
night
$194 per night, originally $341
4.93 out of 5 average rating, 1021 reviews
4.93 (1021)
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)
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
Cudjoe Key Home with a View
Waterfront
Waterfront
Sea views
,
·
Sea views
Jun 22 – 27
Jun 22 – 27
$261
night
$261 per night
4.97 out of 5 average rating, 119 reviews
4.97 (119)
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)
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
Beach House Key West, with a daily rentals license
9 beds
9 beds
Apr 22 – 27
Apr 22 – 27
$1,099
$839
night
$839 per night, originally $1,099
4.59 out of 5 average rating, 27 reviews
4.59 (27)
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
$863
night
$863 per night
5.0 out of 5 average rating, 9 reviews
5.0 (9)
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