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Search results; Over 1,000 homes in Summerland Key

Home in Summerland Key

Kelly’s Kabin - Private FL Keys Cottage

1 bedroom, 3 beds, 1 private bathroom

3–8 Oct

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4.77 out of 5 average rating, 93 reviews

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

10–15 Sept

$1,619 SGD for 5 nights

4.94 out of 5 average rating, 81 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 Oceanside 200' Seawall 3/2 Sleeps 6

3 bedrooms, 3 beds, 2 bathrooms

8–13 Aug

$2,572 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, 1 bathroom

13–18 Sept

$1,164 SGD for 5 nights

4.82 out of 5 average rating, 92 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

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

9–14 Sept

$1,919 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, 1 bathroom

9–14 Sept

$1,743 SGD for 5 nights

+$230 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, 3 bathrooms

27 Sept – 2 Oct

$5,659 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Featured hotel

Room in Key West

Classic Double Queen City/Balcony

2 queen beds, 1 bathroom

9–14 Sept

$1,109 SGD for 5 nights

+$102 SGD Airbnb credit

4.81 out of 5 average rating, 72 reviews

Top guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 bathroom

13–18 Oct

$2,624 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

Featured hotel

Room in Key West

Havana king room

2 king beds, 1 bathroom

9–14 Sept

$1,298 SGD for 5 nights

+$135 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Guest favourite

Villa in Summerland Key

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

6 bedrooms, 7 beds, 6 bathrooms

25–30 Oct

$7,738 SGD for 5 nights

Free cancellation

5.0 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

9–14 Sept

$1,566 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Cudjoe Key

Ocean Breeze Retreat w/ Dock| Keys Escape

2 bedrooms, 4 beds, 2 bathrooms

11–16 Sept

$1,727 SGD for 5 nights

4.88 out of 5 average rating, 8 reviews

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

27 Sept – 2 Oct

$1,353 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

10–15 Sept

$14,653 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Top guest favourite

Home in Cudjoe Key

Keys Island Villa - Venture Out Home 354

2 bedrooms, 2 beds, 2 bathrooms

9–14 Sept

$2,285 SGD for 5 nights

4.95 out of 5 average rating, 92 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