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Search results; Over 1,000 homes in Summerland Key

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

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds

12–17 Sept

$1,586 SGD for 5 nights

4.94 out of 5 average rating, 81 reviews

Guest favourite

Home in Summerland Key

Waterfront Haven House with Boat Basin & Ramp!

3 bedrooms, 6 beds

13–18 Sept

4.93 out of 5 average rating, 127 reviews

Guest favourite

Home in Summerland Key

Waterfront Oceanside 200' Seawall 3/2 Sleeps 6

3 bedrooms, 3 beds

8–13 Aug

$2,579 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds

13–18 Sept

$1,167 SGD for 5 nights

4.82 out of 5 average rating, 92 reviews

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds

11–16 Sept

$1,838 SGD for 5 nights

4.97 out of 5 average rating, 36 reviews

Featured hotel

Hotel in Summerland Key

King room

1 bedroom, 1 king bed

11–16 Sept

$1,647 SGD for 5 nights

+$215 SGD Airbnb credit

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Summerland Key

Waterfront Beach House with Dock & Heated Pool!

4 bedrooms, 5 beds

27 Sept – 2 Oct

$5,675 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Guest favourite

Home in Summerland Key

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

4 bedrooms, 9 beds

25–30 Oct

$6,534 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

Top guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds

13–18 Oct

$2,661 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

Featured hotel

Room in Key West

Classic Double Queen City/Balcony

2 queen beds

11–16 Sept

$1,117 SGD for 5 nights

+$103 SGD Airbnb credit

4.81 out of 5 average rating, 72 reviews

Featured hotel

Room in Key West

Havana king room

2 king beds

11–16 Sept

$1,287 SGD for 5 nights

+$134 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds

12–17 Sept

$1,572 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed

27 Sept – 2 Oct

$1,357 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Guest favourite

Home in Cudjoe Key

Ocean Breeze Retreat w/ Dock| Keys Escape

2 bedrooms, 4 beds

1–6 Dec

$1,754 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 8 reviews

Guest favourite

Villa in Summerland Key

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

6 bedrooms, 7 beds

25–30 Oct

$7,566 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in Cudjoe Key

Keys Island Villa - Venture Out Home 354

2 bedrooms, 2 beds

11–16 Sept

$2,292 SGD for 5 nights

4.95 out of 5 average rating, 92 reviews

Guest favourite

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community

2 bedrooms, 3 beds

28 Sept – 3 Oct

$1,871 SGD for 5 nights

4.97 out of 5 average rating, 131 reviews

Guest favourite

Home in Cudjoe Key

Cudjoe Key Home with a View

2 bedrooms, 3 beds

24–29 Oct

$1,555 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 211 reviews