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Search results; Over 1,000 homes in Upper Sugarloaf Key

Superhost

Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West

2 bedrooms, 3 beds, 1 private bathroom

26 Sept – 1 Oct

,

4.92 out of 5 average rating, 133 reviews

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

6–11 Sept

$1,548 SGD for 5 nights

4.94 out of 5 average rating, 80 reviews

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

9–14 Sept

$1,218 SGD for 5 nights

4.82 out of 5 average rating, 92 reviews

Featured hotel

Room in Key West

Classic Double Queen City/Balcony

2 queen beds, 1 bathroom

7–12 Sept

$1,047 SGD for 5 nights

+$92 SGD Airbnb credit

4.8 out of 5 average rating, 71 reviews

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

5–10 Sept

$2,156 SGD for 5 nights

4.97 out of 5 average rating, 36 reviews

Featured hotel

Room in Key West

Havana king room

2 king beds, 1 bathroom

7–12 Sept

$1,317 SGD for 5 nights

+$138 SGD Airbnb credit

5.0 out of 5 average rating, 3 reviews

Featured hotel

Room in Key West

Ocean view one king bed accessible

1 bathroom

7–12 Sept

$1,175 SGD for 5 nights

+$128 SGD Airbnb credit

New place to stay

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

7–12 Sept

$1,395 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Featured hotel

Hotel in Summerland Key

King room

1 bedroom, 1 king bed, 1 bathroom

5–10 Sept

$1,761 SGD for 5 nights

+$233 SGD Airbnb credit

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Cudjoe Key

Cudjoe Key Home with a View

2 bedrooms, 3 beds, 2 bathrooms

24–29 Oct

$1,555 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 210 reviews

Guest favourite

Home in Summerland Key

9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW

9 bedrooms, 16 beds, 9 bathrooms

26–31 Oct

$16,714 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 19 reviews

Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds, 1 bathroom

6–11 Sept

$1,570 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Featured hotel

Room in Key West

Havana king accessible

1 king bed, 1 bathroom

6–11 Sept

$1,414 SGD for 5 nights

+$153 SGD Airbnb credit

Guest favourite

Villa in Summerland Key

6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW

6 bedrooms, 7 beds, 6 bathrooms

7–12 Sept

$7,146 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

7–12 Sept

$14,694 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Superhost

Apartment in Summerland Key

Standard Suite at Sugarloaf Key Hotel

1 bedroom, 2 beds, 1 bathroom

21–26 Sept

$1,470 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Featured hotel

Hotel in Key West

King city single room

1 bedroom, 1 king bed, 1 bathroom

13–18 Sept

$1,374 SGD for 5 nights

+$157 SGD Airbnb credit

5.0 out of 5 average rating, 25 reviews

Top guest favourite

Home in Summerland Key

Ocean front classic keys cottage

3 bedrooms, 5 beds, 2 bathrooms

1–8 Nov

$4,111 SGD for 7 nights

Free cancellation

4.95 out of 5 average rating, 20 reviews

Top guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 bathroom

13–18 Oct

$2,423 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews