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Search results; Over 1,000 homes in Summerland Key

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 private bathroom

14–19 Sept

$1,908 SGD for 5 nights

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4.97 out of 5 average rating, 36 reviews

Featured hotel

Hotel in Summerland Key

Waterfront two bedroom cottage

1 bedroom, 2 king beds, 1 bathroom

20–25 Sept

$2,608 SGD for 5 nights

+$360 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Featured hotel

Hotel in Key West

Classic Double Queen City/Balcony

1 bedroom, 2 queen beds, 1 bathroom

13–18 Sept

$960 SGD for 5 nights

+$79 SGD Airbnb credit

4.81 out of 5 average rating, 73 reviews

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

14–19 Sept

$1,584 SGD for 5 nights

4.94 out of 5 average rating, 81 reviews

Featured hotel

Hotel in Key West

Havana king room

1 bedroom, 2 king beds, 1 bathroom

13–18 Sept

$1,210 SGD for 5 nights

+$122 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

19–24 Sept

$1,191 SGD for 5 nights

4.82 out of 5 average rating, 93 reviews

Top guest favourite

Home in Summerland Key

Ocean front classic keys cottage

3 bedrooms, 5 beds, 2 bathrooms

1–8 Nov

$4,118 SGD for 7 nights

Free cancellation

4.95 out of 5 average rating, 20 reviews

Guest favourite

Home in Summerland Key

Waterfront Anchor House with Boat Basin & Ramp!

4 bedrooms, 6 beds, 2 bathrooms

16–21 Sept

4.95 out of 5 average rating, 116 reviews

Guest favourite

Home in Summerland Key

Waterfront Captain House with Boat Basin & Ramp!

3 bedrooms, 6 beds, 2 bathrooms

14–19 Sept

4.96 out of 5 average rating, 55 reviews

Guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 bathroom

13–18 Oct

$2,670 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Guest favourite

Home in Summerland Key

4BR Villa | Private Pool & Tiki | 30 Min to KW

4 bedrooms, 9 beds, 4 bathrooms

25–30 Oct

$6,506 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

Featured hotel

Hotel in Key West

Havana king accessible

1 bedroom, 1 king bed, 1 bathroom

13–18 Sept

$1,210 SGD for 5 nights

+$122 SGD Airbnb credit

Luxe

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

14–19 Sept

$14,680 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Guest favourite

Home in Summerland Key

Waterfront Beach House with Dock & Heated Pool!

4 bedrooms, 5 beds, 3 bathrooms

27 Sept – 2 Oct

$5,564 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Guest favourite

Home in Cudjoe Key

Cudjoe Key Home with a View

2 bedrooms, 3 beds, 2 bathrooms

24–29 Oct

$1,554 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 212 reviews

Guest favourite

Home in Big Pine Key

Cozy house with relaxing pool

2 bedrooms, 3 beds, 2 bathrooms

14–19 Nov

$2,572 SGD for 5 nights

Free cancellation

4.83 out of 5 average rating, 12 reviews

Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$1,569 SGD for 5 nights

5.0 out of 5 average rating, 10 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

$16,698 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 19 reviews

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

27 Sept – 2 Oct

$1,356 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews