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Search results; Over 1,000 homes in Summerland Key

Guest favourite

Home in Summerland Key

Waterfront Haven House with Boat Basin & Ramp!

3 bedrooms, 6 beds, 1 private bathroom

13–18 Sept

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4.93 out of 5 average rating, 127 reviews

Top guest favourite

Home in Summerland Key

Ocean front classic keys cottage

3 bedrooms, 5 beds, 2 bathrooms

1–8 Nov

$4,107 SGD for 7 nights

Free cancellation

4.95 out of 5 average rating, 20 reviews

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

6–11 Sept

$1,546 SGD for 5 nights

4.94 out of 5 average rating, 80 reviews

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

6–11 Sept

$1,166 SGD for 5 nights

4.82 out of 5 average rating, 92 reviews

Featured hotel

Hotel in Summerland Key

King room

1 bedroom, 1 king bed, 1 bathroom

6–11 Sept

$1,670 SGD for 5 nights

+$219 SGD Airbnb credit

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Summerland Key

Waterfront Oceanside 200' Seawall 3/2 Sleeps 6

3 bedrooms, 3 beds, 2 bathrooms

8–13 Aug

$2,576 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

4–9 Sept

$2,344 SGD for 5 nights

4.97 out of 5 average rating, 36 reviews

Guest favourite

Home in Summerland Key

Waterfront Beach House with Dock & Heated Pool!

4 bedrooms, 5 beds, 3 bathrooms

27 Sept – 2 Oct

$5,669 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 bathroom

13–18 Oct

$2,428 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

Guest favourite

Villa in Summerland Key

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

6 bedrooms, 7 beds, 6 bathrooms

7–12 Sept

$7,201 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Guest favourite

Tiny home in Big Pine Key

Cottage 30 min from Key West, free parking, pool

1 bedroom, 3 beds, 1 bathroom

8–13 Sept

4.88 out of 5 average rating, 131 reviews

Superhost

Home in Cudjoe Key

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

2 bedrooms, 4 beds, 2 bathrooms

12–17 Sept

4.92 out of 5 average rating, 97 reviews

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

7–12 Sept

$14,680 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Guest favourite

Home in Cudjoe Key

Yellow Home - Receive $400 towards a Boat Rental!

3 bedrooms, 3 beds, 2 bathrooms

13–18 Sept

4.88 out of 5 average rating, 42 reviews

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

Guest favourite

Home in Cudjoe Key

101- Oceanside House with Pool

2 bedrooms, 2 king beds, 3 bathrooms

7–12 Sept

$1,966 SGD for 5 nights

4.89 out of 5 average rating, 258 reviews

Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds, 1 bathroom

6–11 Sept

$1,568 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

7–12 Sept

$1,394 SGD for 5 nights

5.0 out of 5 average rating, 19 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

7–12 Sept

$16,697 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews