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

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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

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Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

6–11 Sept

$1,555 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 80 reviews

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Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

6–11 Sept

$1,173 SGD for 5 nights

4.81 out of 5 average rating, 91 reviews

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Featured hotel

Room in Key West

Ocean view one king bed accessible

1 bathroom

7–12 Sept

$1,191 SGD for 5 nights

+$130 SGD Airbnb credit

Free cancellation

New place to stay

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Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

1–6 Sept

$2,371 SGD for 5 nights

4.97 out of 5 average rating, 36 reviews

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Featured hotel

Room in Key West

Classic Double Queen City/Balcony

2 queen beds, 1 bathroom

7–12 Sept

$1,021 SGD for 5 nights

+$88 SGD Airbnb credit

4.8 out of 5 average rating, 69 reviews

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Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

7–12 Sept

$14,769 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

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Featured hotel

Hotel in Summerland Key

Waterfront two bedroom cottage

1 bedroom, 2 king beds, 1 bathroom

14–19 Oct

$3,095 SGD for 5 nights

+$433 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

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Guest favourite

Home in Summerland Key

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

9 bedrooms, 16 beds, 9 bathrooms

7–12 Sept

$16,799 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

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Superhost

Home in Cudjoe Key

Cudjoe Key Home with a View

2 bedrooms, 3 beds, 2 bathrooms

27 Sept – 2 Oct

$1,397 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 208 reviews

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Guest favourite

Home in Cudjoe Key

Betty's Place

2 bedrooms, 3 beds, 2 bathrooms

18–23 Sept

4.92 out of 5 average rating, 119 reviews

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Boat in Key West

Serenova - 58' Leopard Catamaran

3 bedrooms, 3 queen beds, 2 bathrooms

14–19 Sept

$2,620 SGD for 5 nights

Free cancellation

New place to stay

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Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

5–10 Sept

$1,428 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

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Guest favourite

Boat in Key West

3BR In Resort Village, Pools, Free Kayak & Shuttle

3 bedrooms, 3 beds, 2 bathrooms

7–12 Sept

Free cancellation

4.81 out of 5 average rating, 26 reviews

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Superhost

Villa in Summerland Key

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

6 bedrooms, 7 beds, 6 bathrooms

7–12 Sept

$7,182 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

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Featured hotel

Room in Key West

Havana king room

2 king beds, 1 bathroom

6–11 Sept

$1,638 SGD for 5 nights

+$186 SGD Airbnb credit

Free cancellation

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Home in Cudjoe Key

Oceanfront Cottage with Open Water Views

2 bedrooms, 2 beds, 2 bathrooms

20–25 Sept

$3,604 SGD for 5 nights

5.0 out of 5 average rating, 47 reviews

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Superhost

Home in Cudjoe Key

Blue Heaven Waterfront Home

2 bedrooms, 3 beds, 2 bathrooms

5–10 Sept

4.89 out of 5 average rating, 18 reviews

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Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds, 1 bathroom

7–12 Sept

$1,587 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews