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Search results; Over 1,000 homes in Upper Sugarloaf Key
Over 1,000 homes in Upper Sugarloaf Key
Photo 1 of 6
Superhost
Superhost
Home in Upper Sugarloaf Key
The Lighthouse - Beach Houses Key West
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$5,965 SGD
$4,063 SGD
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for 5 nights
,
·
4.92 out of 5 average rating, 133 reviews
4.92 (133)
Photo 1 of 6
Superhost
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,555 SGD
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for 5 nights
$1,555 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 80 reviews
4.94 (80)
Photo 1 of 6
Superhost
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,173 SGD
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for 5 nights
$1,173 SGD for 5 nights
4.81 out of 5 average rating, 91 reviews
4.81 (91)
Photo 1 of 6
Guest favourite
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom
1 bedroom
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Sept
1–6 Sept
$2,362 SGD
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for 5 nights
$2,362 SGD for 5 nights
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
30 Sept – 5 Oct
30 Sept – 5 Oct
$2,101 SGD
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for 5 nights
$2,101 SGD for 5 nights
4.94 out of 5 average rating, 36 reviews
4.94 (36)
Photo 1 of 6
Guest favourite
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
5–10 Sept
5–10 Sept
$1,428 SGD
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for 5 nights
$1,428 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 6
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4.5 bathrooms
4.5 bathrooms
7–12 Sept
7–12 Sept
$14,769 SGD
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for 5 nights
$14,769 SGD for 5 nights
4.56 out of 5 average rating, 25 reviews
4.56 (25)
Photo 1 of 6
Superhost
Superhost
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms
6 bedrooms
,
·
7 beds
7 beds
,
·
6 bathrooms
6 bathrooms
7–12 Sept
7–12 Sept
$7,182 SGD
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for 5 nights
$7,182 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Summerland Key
9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW
9 bedrooms
9 bedrooms
,
·
16 beds
16 beds
,
·
9 bathrooms
9 bathrooms
7–12 Sept
7–12 Sept
$16,799 SGD
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for 5 nights
$16,799 SGD for 5 nights
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Photo 1 of 6
Superhost
Superhost
Apartment in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Sept
1–6 Sept
$2,079 SGD
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for 5 nights
$2,079 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Cudjoe Key
Oceanside home 109, dock,kayaks,bikes,pool,fishing
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
9–14 Sept
9–14 Sept
$3,091 SGD
$2,504 SGD
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for 5 nights
4.94 out of 5 average rating, 33 reviews
4.94 (33)
Photo 1 of 6
Featured hotel
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,009 SGD
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for 5 nights
$1,009 SGD for 5 nights
+$86 SGD Airbnb credit
4.8 out of 5 average rating, 69 reviews
4.8 (69)
Photo 1 of 6
Superhost
Superhost
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,397 SGD
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for 5 nights
$1,397 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 209 reviews
4.96 (209)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
8–13 Jan
8–13 Jan
$7,112 SGD
$6,265 SGD
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for 5 nights
Free cancellation
4.83 out of 5 average rating, 111 reviews
4.83 (111)
Photo 1 of 6
Superhost
Superhost
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
4 bathrooms
4 bathrooms
5–10 Oct
5–10 Oct
$6,666 SGD
$5,858 SGD
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for 5 nights
Free cancellation
4.89 out of 5 average rating, 103 reviews
4.89 (103)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
31 Oct – 5 Nov
31 Oct – 5 Nov
$4,082 SGD
$2,131 SGD
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for 5 nights
Free cancellation
4.89 out of 5 average rating, 158 reviews
4.89 (158)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Cudjoe Key
101- Oceanside House with Pool
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
3 bathrooms
3 bathrooms
1–6 Sept
1–6 Sept
$2,776 SGD
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for 5 nights
$2,776 SGD for 5 nights
4.89 out of 5 average rating, 258 reviews
4.89 (258)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$3,329 SGD
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for 5 nights
$3,329 SGD for 5 nights
4.93 out of 5 average rating, 127 reviews
4.93 (127)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$3,344 SGD
$2,216 SGD
Show price breakdown
for 5 nights
4.88 out of 5 average rating, 42 reviews
4.88 (42)
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