Search results; Over 1,000 places

Prices include all fees
Guest favorite
Home in Sugarloaf Key
Azucar - Beach Houses Key West
7 beds
Aug 11 – 16
R117,946 ZAR for 5 nights
for 5 nights
4.8 out of 5 average rating, 146 reviews
Guest favorite
Home in Upper Sugarloaf Key
Lighthouse - Beach Houses Key West
1 sofa bed
Jul 28 – Aug 2
R115,488 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 89 reviews
Guest favorite
Home in Upper Sugarloaf Key
Hemingway - Beach Houses Key West
3 beds
Jul 10 – 15
R104,057 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 100 reviews
Superhost
Tiny home in Big Pine Key
Cheerful Tiny House in the Florida Keys
Free cancellation
Jun 2 – 7
R19,104 ZAR for 5 nights, originally R21,655 ZAR
for 5 nights
4.81 out of 5 average rating, 190 reviews
Guest favorite
Camper/RV in Big Pine Key
Having fun in the lower Keys
2 beds
Jun 3 – 8
R11,516 ZAR for 5 nights, originally R13,368 ZAR
for 5 nights
4.9 out of 5 average rating, 79 reviews
Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
Free cancellation
Jul 6 – 11
R26,281 ZAR for 5 nights
for 5 nights
4.82 out of 5 average rating, 55 reviews
Superhost
Home in Summerland Key
Pelico Palms Sunset Suites
4 beds
Jun 8 – 13
R52,691 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 36 reviews
Superhost
Home in Sugarloaf Key
Main House - Sugarloaf Beach Key West
6 beds
Jun 1 – 6
R126,812 ZAR for 5 nights, originally R187,753 ZAR
for 5 nights
4.76 out of 5 average rating, 98 reviews
Superhost
Houseboat in Big Pine Key
1 Bedroom Aqualodge # 6 Tarpon
1 queen bed
Jun 1 – 6
R15,643 ZAR for 5 nights
for 5 nights
4.78 out of 5 average rating, 32 reviews
Home in Summerland Key
A month in paradise pool home.
Free cancellation
Sep 7 – 12
R42,200 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Houseboat in Key West
Deluxe Bungalow
4 beds
Jun 22 – 27
R19,102 ZAR for 5 nights
for 5 nights
4.72 out of 5 average rating, 180 reviews
Guest favorite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
3 beds
Jun 9 – 14
R31,922 ZAR for 5 nights, originally R41,810 ZAR
for 5 nights
4.93 out of 5 average rating, 126 reviews
Guest favorite
Home in Cudjoe Key
Betty's Place
3 beds
Jun 10 – 15
R32,905 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 54 reviews
Superhost
Home in Cudjoe Key
Waterfront FL Keys Cottage @ Venture Out
Free cancellation
Aug 10 – 15
R23,503 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 28 reviews
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Top guest favorite
Home in Cudjoe Key
Cudjoe Bay- Newly Renovated Oceanviews with Pool
2 king beds
Jun 7 – 12
R34,668 ZAR for 5 nights, originally R38,713 ZAR
for 5 nights
4.93 out of 5 average rating, 177 reviews
Superhost
Home in Sugarloaf Key
Hammock House - Beach Houses Key West
4 beds
Jul 14 – 19
R180,978 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 20 reviews
Guest favorite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
Free cancellation
Jun 21 – 26
R19,637 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 43 reviews
Guest favorite
Home in Cudjoe Key
Cudjoe Key Home with a View
Free cancellation
Aug 25 – 30
R33,653 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 157 reviews