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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

12–17 Sept

$1,586 SGD for 5 nights

4.94 out of 5 average rating, 81 reviews

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

13–18 Sept

$1,167 SGD for 5 nights

4.82 out of 5 average rating, 92 reviews

Featured hotel

Room in Key West

Havana king room

2 king beds, 1 bathroom

11–16 Sept

$1,287 SGD for 5 nights

+$134 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

11–16 Sept

$1,918 SGD for 5 nights

4.97 out of 5 average rating, 36 reviews

Featured hotel

Room in Key West

Hearing Accessible Classic King City/Balcony

1 king bed, 1 bathroom

27 Sept – 2 Oct

$921 SGD for 5 nights

+$73 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Featured hotel

Hotel in Summerland Key

King room

1 bedroom, 1 king bed, 1 bathroom

11–16 Sept

$1,469 SGD for 5 nights

+$189 SGD Airbnb credit

5.0 out of 5 average rating, 10 reviews

Featured hotel

Room in Key West

Havana king accessible

1 king bed, 1 bathroom

11–16 Sept

$1,287 SGD for 5 nights

+$134 SGD Airbnb credit

Featured hotel

Room in Key West

Queen Room

1 queen bed, 1 bathroom

15–20 Sept

$817 SGD for 5 nights

+$122 SGD Airbnb credit

5.0 out of 5 average rating, 15 reviews

Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds, 1 bathroom

12–17 Sept

$1,572 SGD for 5 nights

5.0 out of 5 average rating, 9 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, 211 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

$16,715 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 19 reviews

Featured hotel

Hotel in Key West

King city single room

1 bedroom, 1 king bed, 1 bathroom

13–18 Sept

$1,590 SGD for 5 nights

+$190 SGD Airbnb credit

5.0 out of 5 average rating, 25 reviews

Luxe

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

12–17 Sept

$14,695 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

27 Sept – 2 Oct

$1,357 SGD for 5 nights

5.0 out of 5 average rating, 19 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

Superhost

Home in Sugarloaf Key

Mi Azucar

2 bedrooms, 7 beds, 3 bathrooms

27 Sept – 2 Oct

4.81 out of 5 average rating, 175 reviews

Home in Cudjoe Key

Private Secluded Ocean View & Pool Near Key West

4 bedrooms, 4 beds, 2 bathrooms

15–20 Sept

New place to stay

Guest favourite

Home in Cudjoe Key

Blue Heaven Waterfront Home

2 bedrooms, 3 beds, 2 bathrooms

12–17 Sept

4.89 out of 5 average rating, 18 reviews