Search results; Over 1,000 places in Summerland Key

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Guest favorite
Home in Summerland Key
Sailfish Dream on Cudjoe Key-28 day minimum
6 guests2 bedrooms3 beds2 baths
Aug 17 – 22
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Aug 17 – 22
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R22,539 ZAR for 5 nights
for 5 nights

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Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
Free cancellation
Aug 24 – 29
R26,403 ZAR for 5 nights
for 5 nights
4.82 out of 5 average rating, 57 reviews
Guest favorite
Home in Cudjoe Key
Cudjoe Key Home with a View
Free cancellation
Sep 7 – 12
R22,539 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 159 reviews
Superhost
Tiny home in Big Pine Key
Cheerful Tiny House in the Florida Keys
Free cancellation
Aug 2 – 7
R18,848 ZAR for 5 nights
for 5 nights
4.81 out of 5 average rating, 196 reviews
Camper/RV in Cudjoe Key
Rv lot in paradise
1 bed
Jun 20 – 25
R10,733 ZAR for 5 nights
for 5 nights
New place to stay
Home in Cudjoe Key
Lobster Season, Park Place, Waterfront, special
Free cancellation
Jul 12 – 17
R27,906 ZAR for 5 nights
for 5 nights
New place to stay
Superhost
Home in Cudjoe Key
Waterfront Venture Out Home
1 queen bed
Jun 21 – 26
R21,573 ZAR for 5 nights
for 5 nights
4.83 out of 5 average rating, 66 reviews
Guest favorite
Home in Cudjoe Key
Private Ocean Oasis by Key West, Florida
4 beds
Jul 19 – 24
R33,272 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 54 reviews
Home in Cudjoe Key
Dolphin Daze
Free cancellation
Dec 9 – 14
R35,687 ZAR for 5 nights
for 5 nights
Home in Cudjoe Key
Lochloosa in Cudjoe Key #655-open lobster season!
Free cancellation
Jul 6 – 11
R22,539 ZAR for 5 nights
for 5 nights
New place to stay
Top guest favorite
Camper/RV in Big Pine Key
Beautiful Private Camper Nature
Free cancellation
Jun 29 – Jul 4
R10,583 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
2 beds
Aug 17 – 22
R46,044 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 107 reviews
Superhost
Home in Little Torch Key
Indulge yourself. It's heavenly in Little Torch
Free cancellation
Aug 25 – Sep 1
R31,447 ZAR for 7 nights
for 7 nights
4.8 out of 5 average rating, 15 reviews
Guest favorite
Tiny home in Summerland Key
Bungalow
1 bed
Jun 22 – 27
R19,942 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Superhost
Cottage in Cudjoe Key
Calypso Cottage
4 beds
Jun 30 – Jul 5
R31,555 ZAR for 5 nights
for 5 nights
4.71 out of 5 average rating, 152 reviews
Guest favorite
Villa in Cudjoe Key
Howard House on the Sea
2 beds
Jun 26 – Jul 1
R38,102 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 22 reviews
Guest favorite
Home in Cudjoe Key
Waterfront 35’ Dock,80’ pool,20 min Key West
3 beds
Jun 20 – 25
R34,238 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 47 reviews
Guest favorite
Camper/RV in Big Pine Key
Having fun in the lower Keys
2 beds
Jul 6 – 11
R12,944 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 83 reviews
Guest favorite
Hotel in Summerland Key
Two twin beds for friends traveling together
2 single beds
Jun 25 – 30
R18,645 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews