Search results; Over 1,000 homes in Summerland Key

Photo 1 of 29

Guest favourite

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

1 bedroom, 3 beds, 1 private bathroom

13–18 Oct

$2,637 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Photo 1 of 17

Featured hotel

Hotel in Summerland Key

Parmer's Resort, King room

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

$1,530 SGD for 5 nights

+$198 SGD Airbnb credit

5.0 out of 5 average rating, 10 reviews

Photo 1 of 18

Superhost

Tiny home in Summerland Key

Cottage

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

$1,736 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 82 reviews

Photo 1 of 18

Superhost

Tiny home in Summerland Key

Bungalow

1 bedroom, 2 beds, 1 bathroom

1–6 Oct

$1,353 SGD for 5 nights

4.82 out of 5 average rating, 95 reviews

Photo 1 of 24

Guest favourite

Home in Summerland Key

Anchor House

4 bedrooms, 7 beds, 2 bathrooms

1–6 Oct

$5,107 SGD for 5 nights

4.95 out of 5 average rating, 116 reviews

Photo 1 of 25

Guest favourite

Home in Summerland Key

Captain House

3 bedrooms, 6 beds, 2 bathrooms

1–6 Oct

$4,649 SGD for 5 nights

4.96 out of 5 average rating, 55 reviews

Photo 1 of 29

Guest favourite

Apartment in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

1 bedroom, 4 beds, 1 bathroom

1–6 Oct

$1,801 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 37 reviews

Photo 1 of 29

Guest favourite

Home in Summerland Key

Waterfront Oceanside 200' Seawall 3/2 Sleeps 6

3 bedrooms, 3 beds, 2 bathrooms

8–13 Aug

$2,202 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Photo 1 of 29

Guest favourite

Home in Summerland Key

Barry Beach

4 bedrooms, 5 beds, 3 bathrooms

13–18 Oct

$6,355 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Photo 1 of 6

Guest favourite

Tiny home in Summerland Key

Waterview Bungalow

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

$1,545 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Photo 1 of 29

Luxe

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds, 4.5 bathrooms

1–6 Oct

$15,156 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Photo 1 of 29

Guest favourite

Home in Summerland Key

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

4 bedrooms, 9 beds, 4 bathrooms

19–24 Oct

$6,664 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Photo 1 of 29

Superhost

Home in Cudjoe Key

Oceanfront with 50’ Dock & Stunning Views

2 bedrooms, 5 beds, 2 bathrooms

12–17 Oct

$2,181 SGD for 5 nights

New place to stay

Photo 1 of 29

Home in Big Pine Key

Your Perfect Florida Keys Escape

3 bedrooms, 3 beds, 2 bathrooms

9–14 Nov

$2,553 SGD for 5 nights

Free cancellation

New place to stay

Photo 1 of 21

Featured hotel

Hotel in Key West

Havana Cabana at Key West, Havana 2 queens

1 bedroom, 2 queen beds, 1 bathroom

1–6 Oct

$1,670 SGD for 5 nights

+$191 SGD Airbnb credit

Free cancellation

Photo 1 of 29

Guest favourite

Villa in Summerland Key

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

6 bedrooms, 7 beds, 6 bathrooms

19–24 Oct

$8,687 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Photo 1 of 29

Guest favourite

Home in Cudjoe Key

105- Newly renovated house with ocean view & pool

2 bedrooms, 2 king beds, 3 bathrooms

1–6 Oct

$2,693 SGD for 5 nights

4.88 out of 5 average rating, 16 reviews

Photo 1 of 29

Superhost

Home in Cudjoe Key

Latitudes & Attitudes

3 bedrooms, 5 beds, 2 bathrooms

16–23 Nov

$7,634 SGD for 7 nights

Free cancellation

Photo 1 of 29

Guest favourite

Home in Cudjoe Key

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

2 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

$3,799 SGD for 5 nights

4.94 out of 5 average rating, 18 reviews

Search results; Over 1,000 homes in Summerland KeyOver 1,000 homes in Summerland Key

Search results; Over 1,000 homes in Summerland Key