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Homes in Upper Sugarloaf Key
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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 29
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
$5,949 SGD
$4,051 SGD
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for 5 nights
,
·
4.92 out of 5 average rating, 133 reviews
4.92 (133)
Photo 1 of 18
Guest favourite
Guest favourite
Tiny home in Summerland Key
Bungalow
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,351 SGD
$1,170 SGD
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for 5 nights
4.82 out of 5 average rating, 92 reviews
4.82 (92)
Photo 1 of 18
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
$1,551 SGD
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for 5 nights
$1,551 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 80 reviews
4.94 (80)
Photo 1 of 6
Featured hotel
Featured hotel
Room in Key West
Ocean view one king bed accessible
1 bathroom
1 bathroom
5–10 Sept
5–10 Sept
$1,411 SGD
Show price breakdown
for 5 nights
$1,411 SGD for 5 nights
+$163 SGD Airbnb credit
New place to stay
New
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
19–24 Sept
19–24 Sept
$1,018 SGD
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for 5 nights
$1,018 SGD for 5 nights
+$88 SGD Airbnb credit
4.8 out of 5 average rating, 69 reviews
4.8 (69)
Photo 1 of 29
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
$2,410 SGD
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for 5 nights
$2,410 SGD for 5 nights
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Photo 1 of 6
Featured hotel
Featured hotel
Room in Key West
Havana king room
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,480 SGD
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for 5 nights
$1,480 SGD for 5 nights
+$163 SGD Airbnb credit
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 17
Featured hotel
Featured hotel
Hotel in Summerland Key
King room
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
1–6 Sept
1–6 Sept
$1,676 SGD
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for 5 nights
$1,676 SGD for 5 nights
+$220 SGD Airbnb credit
5.0 out of 5 average rating, 10 reviews
5.0 (10)
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
7–12 Sept
7–12 Sept
$1,598 SGD
$1,399 SGD
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for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
24–29 Oct
24–29 Oct
$1,559 SGD
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for 5 nights
$1,559 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 209 reviews
4.96 (209)
Photo 1 of 29
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
$14,728 SGD
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for 5 nights
$14,728 SGD for 5 nights
4.56 out of 5 average rating, 25 reviews
4.56 (25)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,575 SGD
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for 5 nights
$1,575 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
5–10 Sept
5–10 Sept
$1,687 SGD
$1,525 SGD
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for 5 nights
4.89 out of 5 average rating, 18 reviews
4.89 (18)
Photo 1 of 29
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
13–18 Oct
13–18 Oct
$2,468 SGD
Show price breakdown
for 5 nights
$2,468 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 38 reviews
4.95 (38)
Photo 1 of 24
Top guest favourite
Guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
16–21 Sept
16–21 Sept
$3,872 SGD
$3,459 SGD
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for 5 nights
4.91 out of 5 average rating, 75 reviews
4.91 (75)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Cudjoe Key
Tiki Time in Cudjoe Key 136
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$3,114 SGD
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for 5 nights
$3,114 SGD for 5 nights
4.97 out of 5 average rating, 58 reviews
4.97 (58)
Photo 1 of 29
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
$16,752 SGD
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for 5 nights
$16,752 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 29
Guest favourite
Guest favourite
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
$7,163 SGD
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for 5 nights
$7,163 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Photo 1 of 27
Guest favourite
Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
5–10 Sept
5–10 Sept
$2,766 SGD
$2,013 SGD
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for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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