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Search results; Over 1,000 homes in Summerland Key

Home in Summerland Key

Powell Family Resort

6 bedrooms, 7 beds, 3 private bathrooms

15–20 Aug

$6,205 SGD for 5 nights

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4.86 out of 5 average rating, 42 reviews

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

8–13 Aug

$13,212 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Top guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 bathroom

23–28 Aug

$2,220 SGD for 5 nights

4.97 out of 5 average rating, 32 reviews

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

9–14 Aug

$1,502 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 74 reviews

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

9–14 Aug

$2,046 SGD for 5 nights

4.97 out of 5 average rating, 34 reviews

Guest favourite

Home in Summerland Key

Waterfront Beach House with Dock & Heated Pool!

4 bedrooms, 5 beds, 3 bathrooms

27 Sept – 2 Oct

$5,744 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews

Guest favourite

Home in Summerland Key

Waterfront Anchor House with Boat Basin & Ramp!

4 bedrooms, 6 beds, 2 bathrooms

8–13 Aug

$5,814 SGD for 5 nights

4.95 out of 5 average rating, 116 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

$9,432 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Summerland Key

Waterfront Captain House with Boat Basin & Ramp!

3 bedrooms, 6 beds, 2 bathrooms

8–13 Aug

$5,241 SGD for 5 nights

4.96 out of 5 average rating, 54 reviews

Top guest favourite

Casa particular in Summerland Key

The Retiro House

3 bedrooms, 4 beds, 2 bathrooms

31 Aug – 5 Sept

$3,833 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 9 reviews

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

12–17 Aug

$1,181 SGD for 5 nights

4.8 out of 5 average rating, 83 reviews

Guest favourite

Home in Cudjoe Key

Ocean Breeze Retreat w/ Dock| Keys Escape

2 bedrooms, 4 beds, 2 bathrooms

24–29 Aug

$1,929 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Summerland Key

9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW

9 bedrooms, 15 beds, 9 bathrooms

7–12 Sept

$16,917 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

Home in Marathon

Casa Entera Frente al Mar + Muelle 50'

3 bedrooms, 4 beds, 2 bathrooms

8–15 Aug

$4,454 SGD for 7 nights

Free cancellation

New place to stay

Top guest favourite

Home in Cudjoe Key

Keys Island Villa - Venture Out Home 354

2 bedrooms, 2 beds, 2 bathrooms

9–14 Aug

$2,647 SGD for 5 nights

4.94 out of 5 average rating, 89 reviews

Guest favourite

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

5 bedrooms, 6 beds, 3 bathrooms

26 Sept – 1 Oct

4.83 out of 5 average rating, 111 reviews

Guest favourite

Home in Big Pine Key

Fishermen's Paradise | Pool, 220' Dock & Open-Wate

3 bedrooms, 3 beds, 4 bathrooms

5–10 Oct

$6,725 SGD for 5 nights

4.91 out of 5 average rating, 101 reviews

Guest favourite

Home in Cudjoe Key

Betty's Place

2 bedrooms, 3 beds, 2 bathrooms

14–19 Aug

4.91 out of 5 average rating, 117 reviews

Top guest favourite

Home in Cudjoe Key

Oceanfront Cottage with Open Water Views

2 bedrooms, 2 beds, 2 bathrooms

23–28 Aug

$3,297 SGD for 5 nights

5.0 out of 5 average rating, 45 reviews