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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 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
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
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
Top guest favourite
Guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$3,737 SGD
$3,291 SGD
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for 5 nights
5.0 out of 5 average rating, 47 reviews
5.0 (47)
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
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
Show price breakdown
for 5 nights
$2,101 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 36 reviews
4.94 (36)
Photo 1 of 6
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
$1,587 SGD
Show price breakdown
for 5 nights
$1,587 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 6
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
$3,123 SGD
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for 5 nights
$3,123 SGD for 5 nights
4.96 out of 5 average rating, 57 reviews
4.96 (57)
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
Featured hotel
Featured hotel
Room in Key West
Ocean view one king bed accessible
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,191 SGD
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for 5 nights
$1,191 SGD for 5 nights
+$130 SGD Airbnb credit
Free cancellation
New place to stay
New
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
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Sept
1–6 Sept
$3,856 SGD
$3,502 SGD
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for 5 nights
4.89 out of 5 average rating, 184 reviews
4.89 (184)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Cudjoe Key
Oceanside home 107,dock,kayaks,bikes,pool,fishing,
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
7–12 Sept
7–12 Sept
$2,945 SGD
$2,356 SGD
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for 5 nights
4.94 out of 5 average rating, 34 reviews
4.94 (34)
Photo 1 of 6
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
$3,883 SGD
$3,468 SGD
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for 5 nights
4.91 out of 5 average rating, 75 reviews
4.91 (75)
Photo 1 of 6
Superhost
Superhost
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
$1,692 SGD
$1,529 SGD
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for 5 nights
4.89 out of 5 average rating, 18 reviews
4.89 (18)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$2,288 SGD
$1,626 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 74 reviews
4.99 (74)
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