Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Summerland Key
Check in / Check out
Any week
Guests
Add guests
Become a host
Languages & currency
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Summerland Key
Over 1,000 homes in Summerland Key
Photo 1 of 29
Guest favourite
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom
,
·
4 beds
,
·
1 private bathroom
1–6 Oct
1–6 Oct
$1,801 SGD
Show price breakdown
for 5 nights
$1,801 SGD for 5 nights
,
·
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Photo 1 of 18
Superhost
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,736 SGD
Show price breakdown
for 5 nights
$1,736 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 82 reviews
4.94 (82)
Photo 1 of 24
Guest favourite
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$5,607 SGD
$5,099 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 116 reviews
4.95 (116)
Photo 1 of 18
Superhost
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,353 SGD
Show price breakdown
for 5 nights
$1,353 SGD for 5 nights
4.82 out of 5 average rating, 95 reviews
4.82 (95)
Photo 1 of 25
Guest favourite
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$5,112 SGD
$4,649 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 55 reviews
4.96 (55)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
13–18 Oct
13–18 Oct
$2,642 SGD
Show price breakdown
for 5 nights
$2,642 SGD for 5 nights
4.95 out of 5 average rating, 39 reviews
4.95 (39)
Photo 1 of 29
Superhost
Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
10–17 Oct
10–17 Oct
$3,001 SGD
$2,739 SGD
Show price breakdown
for 7 nights
Weekly discount
Free cancellation
New place to stay
New
Photo 1 of 29
Guest favourite
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
16–21 Oct
16–21 Oct
$1,619 SGD
Show price breakdown
for 5 nights
$1,619 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 213 reviews
4.96 (213)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
13–18 Oct
13–18 Oct
$5,950 SGD
Show price breakdown
for 5 nights
$5,950 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Summerland Key
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
8–13 Aug
8–13 Aug
$2,202 SGD
Show price breakdown
for 5 nights
$2,202 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,513 SGD
$1,343 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Photo 1 of 29
Guest favourite
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms
6 bedrooms
,
·
7 beds
7 beds
,
·
6 bathrooms
6 bathrooms
25–30 Oct
25–30 Oct
$7,709 SGD
Show price breakdown
for 5 nights
$7,709 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Photo 1 of 29
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
10–15 Oct
10–15 Oct
$4,610 SGD
Show price breakdown
for 5 nights
$4,610 SGD for 5 nights
New place to stay
New
Photo 1 of 29
Guest favourite
Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms
4 bedrooms
,
·
9 beds
9 beds
,
·
4 bathrooms
4 bathrooms
25–30 Oct
25–30 Oct
$6,553 SGD
Show price breakdown
for 5 nights
$6,553 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 39 reviews
4.95 (39)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
7–12 Oct
7–12 Oct
$4,042 SGD
Show price breakdown
for 5 nights
$4,042 SGD for 5 nights
5.0 out of 5 average rating, 51 reviews
5.0 (51)
Photo 1 of 6
Guest favourite
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,545 SGD
Show price breakdown
for 5 nights
$1,545 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Cudjoe Key
Oceanfront 2BR in Venture Out - 35’ Dock + Pool
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$3,871 SGD
Show price breakdown
for 5 nights
$3,871 SGD for 5 nights
4.94 out of 5 average rating, 18 reviews
4.94 (18)
Photo 1 of 24
Top guest favourite
Guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$3,932 SGD
$3,511 SGD
Show price breakdown
for 5 nights
4.91 out of 5 average rating, 75 reviews
4.91 (75)
Photo 1 of 21
Guest favourite
Guest favourite
Home in Cudjoe Key
101- Oceanside House with Pool
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
3 bathrooms
3 bathrooms
1–6 Oct
1–6 Oct
$1,981 SGD
Show price breakdown
for 5 nights
$1,981 SGD for 5 nights
4.89 out of 5 average rating, 259 reviews
4.89 (259)
1
2
3
4
…
15