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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

15–20 Sept

$2,036 SGD for 5 nights

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4.97 out of 5 average rating, 37 reviews

Featured hotel

Hotel in Summerland Key

Waterfront two bedroom cottage

1 bedroom, 2 king beds, 1 bathroom

14–19 Oct

$3,199 SGD for 5 nights

+$448 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

$1,195 SGD for 5 nights

4.82 out of 5 average rating, 94 reviews

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

16–21 Sept

$1,626 SGD for 5 nights

4.94 out of 5 average rating, 81 reviews

Top guest favourite

Home in Summerland Key

Ocean front classic keys cottage

3 bedrooms, 5 beds, 2 bathrooms

8–15 Dec

$4,126 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

15–20 Sept

4.96 out of 5 average rating, 55 reviews

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

27 Sept – 2 Oct

$1,360 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Superhost

Cottage in Little Torch Key

Waterfront Cozy Cottage with Boat Ramp & Dock!

2 bedrooms, 4 beds, 1 bathroom

18–23 Sept

4.89 out of 5 average rating, 185 reviews

Featured hotel

Hotel in Key West

Classic Double Queen City/Balcony

1 bedroom, 2 queen beds, 1 bathroom

15–20 Sept

$1,130 SGD for 5 nights

+$105 SGD Airbnb credit

4.81 out of 5 average rating, 74 reviews

Featured hotel

Rooms in Marathon

Superior two bedroom suite

2 bedrooms, 1 bathroom

20–25 Sept

$1,773 SGD for 5 nights

+$265 SGD Airbnb credit

Guest favourite

Home in Summerland Key

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

4 bedrooms, 9 beds, 4 bathrooms

25–30 Oct

$6,524 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

Top guest favourite

Home in Cudjoe Key

Oceanfront Cottage with Open Water Views

2 bedrooms, 2 beds, 2 bathrooms

20–25 Sept

5.0 out of 5 average rating, 50 reviews

Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds, 1 bathroom

15–20 Sept

$1,573 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Luxe

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

16–21 Sept

$14,720 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 bathroom

13–18 Oct

$2,672 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Guest favourite

Home in Cudjoe Key

Blue Heaven Waterfront Home

2 bedrooms, 3 beds, 2 bathrooms

26 Sept – 1 Oct

$1,556 SGD for 5 nights

4.89 out of 5 average rating, 18 reviews

Superhost

Home in Cudjoe Key

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

2 bedrooms, 4 beds, 2 bathrooms

16–21 Sept

4.92 out of 5 average rating, 97 reviews

Guest favourite

Home in Summerland Key

Waterfront Beach House with Dock & Heated Pool!

4 bedrooms, 5 beds, 3 bathrooms

27 Sept – 2 Oct

$5,368 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews