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Search results; Over 1,000 homes in Summerland Key

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Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 private bathroom

19–24 Sept

$1,847 SGD for 5 nights

,

4.97 out of 5 average rating, 37 reviews

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Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds

20–25 Sept

$1,560 SGD for 5 nights

4.94 out of 5 average rating, 82 reviews

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Guest favourite

Home in Summerland Key

Waterfront Anchor House with Boat Basin & Ramp!

4 bedrooms, 6 beds

17–22 Sept

4.95 out of 5 average rating, 116 reviews

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Guest favourite

Home in Summerland Key

Waterfront Oceanside 200' Seawall 3/2 Sleeps 6

3 bedrooms, 3 beds

8–13 Aug

$2,205 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

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Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds

20–25 Sept

$1,176 SGD for 5 nights

4.82 out of 5 average rating, 94 reviews

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Guest favourite

Home in Summerland Key

Waterfront Captain House with Boat Basin & Ramp!

3 bedrooms, 6 beds

17–22 Sept

4.96 out of 5 average rating, 55 reviews

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Guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds

13–18 Oct

$2,655 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

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Guest favourite

Home in Summerland Key

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

4 bedrooms, 9 beds

25–30 Oct

$6,562 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 39 reviews

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Guest favourite

Home in Summerland Key

Waterfront Beach House with Dock & Heated Pool!

4 bedrooms, 5 beds

27 Sept – 2 Oct

5.0 out of 5 average rating, 16 reviews

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Featured hotel

Hotel in Summerland Key

Waterfront two bedroom cottage

1 bedroom, 2 king beds

22–27 Sept

$2,886 SGD for 5 nights

+$401 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

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Featured hotel

Hotel in Key West

Classic Double Queen City/Balcony

1 bedroom, 2 queen beds

3–8 Oct

$1,188 SGD for 5 nights

+$113 SGD Airbnb credit

4.8 out of 5 average rating, 76 reviews

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Featured hotel

Hotel in Key West

Havana 2 queens

1 bedroom, 2 queen beds

17–22 Sept

$1,376 SGD for 5 nights

+$147 SGD Airbnb credit

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Guest favourite

Villa in Summerland Key

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

6 bedrooms, 7 beds

25–30 Oct

$7,575 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 12 reviews

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Guest favourite

Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

2 bedrooms, 4 beds

25–30 Sept

Free cancellation

5.0 out of 5 average rating, 10 reviews

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Home in Big Pine Key

Your Perfect Florida Keys Escape

3 bedrooms, 3 beds

17–22 Sept

$2,556 SGD for 5 nights

New place to stay

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Guest favourite

Home in Cudjoe Key

Cudjoe Key Home with a View

2 bedrooms, 3 beds

16–21 Oct

$1,621 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 212 reviews

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Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed

27 Sept – 2 Oct

$1,368 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

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Guest favourite

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

5 bedrooms, 6 beds

2–7 Nov

4.83 out of 5 average rating, 112 reviews

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Guest favourite

Home in Cudjoe Key

105- Newly renovated house with ocean view & pool

2 bedrooms, 2 king beds

17–22 Sept

$2,697 SGD for 5 nights

4.88 out of 5 average rating, 16 reviews