Search results; Over 1,000 homes in Summerland Key

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Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
3 beds
Sep 28 – Oct 3
ﺩ.ﺇ5,597 for 5 nights
4.8 out of 5 average rating, 65 reviews
Guest favorite
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
2 queen beds
Sep 23 – 28
ﺩ.ﺇ2,530 for 5 nights, originally ﺩ.ﺇ2,735
4.76 out of 5 average rating, 21 reviews
Home in Cudjoe Key
35’ dock/Completely Remodeled VO 366
4 beds
Sep 30 – Oct 5
ﺩ.ﺇ4,926 for 5 nights, originally ﺩ.ﺇ6,215
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Cudjoe Key
106- Newly Renovated House with Oceanview and Pool
2 king beds
Sep 18 – 23
ﺩ.ﺇ7,297 for 5 nights
4.93 out of 5 average rating, 185 reviews
Superhost
Hotel in Summerland Key
New 90ft beach & fab sunset views
2 queen beds
Sep 21 – 26
ﺩ.ﺇ3,112 for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Guest suite in Big Pine Key
Old Island Life
1 queen bed
Sep 22 – 27
ﺩ.ﺇ2,691 for 5 nights
4.88 out of 5 average rating, 541 reviews
Superhost
Hotel in Summerland Key
Family friendly escape in the Lower Florida Keys
1 king bed
Sep 23 – 28
ﺩ.ﺇ3,495 for 5 nights
Guest favorite
Apartment in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
2 beds
Sep 27 – Oct 2
ﺩ.ﺇ2,907 for 5 nights, originally ﺩ.ﺇ3,751
4.94 out of 5 average rating, 49 reviews
Guest favorite
Campsite in Cudjoe Key
"Venture Out" Waterfront RV Lot~35' Dockage!
Sep 19 – 24
ﺩ.ﺇ1,699 for 5 nights
4.9 out of 5 average rating, 60 reviews
Top guest favorite
Home in Cudjoe Key
Sept. Special, WF Boat dock, sec. to open water
3 beds
Sep 18 – 23
ﺩ.ﺇ5,296 for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Tiny home in Summerland Key
Lakefront Bungalow
1 bed
Sep 20 – 25
ﺩ.ﺇ5,476 for 5 nights
5.0 out of 5 average rating, 10 reviews
Guest favorite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
3 beds
Dec 2 – 7
ﺩ.ﺇ8,369 for 5 nights
4.93 out of 5 average rating, 135 reviews
Superhost
Apartment in Marathon
Knight's Key Suites Deluxe King Room w/ Kitchen
1 bed
Sep 18 – 23
ﺩ.ﺇ2,164 for 5 nights
4.84 out of 5 average rating, 146 reviews
Superhost
Home in Cudjoe Key
Relaxing Home in the Keys
2 beds
Sep 25 – 30
ﺩ.ﺇ4,241 for 5 nights
4.85 out of 5 average rating, 48 reviews
Top guest favorite
Boat in Key West
Off Grid Boat "Shanty Pineapple" Key West
1 bed
Sep 20 – 25
ﺩ.ﺇ5,147 for 5 nights
4.97 out of 5 average rating, 30 reviews
Guest favorite
Home in Cudjoe Key
Ocean's Edge at Venture Out 137
4 beds
Jan 6 – 11
ﺩ.ﺇ9,235 for 5 nights
4.97 out of 5 average rating, 39 reviews
Guest favorite
Cabin in Marathon
Beautiful Views New Cabin 2/1
4 beds
Sep 28 – Oct 3
ﺩ.ﺇ2,682 for 5 nights, originally ﺩ.ﺇ2,903
4.79 out of 5 average rating, 24 reviews
Guest favorite
Boat in Key West
Tiki Suites ~ The Grand Tiki
1 bed
Sep 21 – 26
ﺩ.ﺇ13,303 for 5 nights
4.91 out of 5 average rating, 317 reviews