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Search results; Over 1,000 places

Superhost
Home in Cudjoe Key
Cozy Venture Out Cottage!
10-min drive
21–26 Apr
4.53 out of 5 average rating, 64 reviews
Guest favourite
Home in Cudjoe Key
May Extravaganza - Relax in Paradise!
8-min drive
1–8 Oct
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
11-min drive
22–27 Jun
4.97 out of 5 average rating, 119 reviews
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
12-min drive
28 Apr – 3 May
4.86 out of 5 average rating, 42 reviews
Home in Cudjoe Key
"Venture Out" into the Sun & Sea
11-min drive
26–31 May
New place to stay
Flat in Big Pine Key
New Deluxe Duplex Unit 1 Queen Bed, Full Kitchen
20-min drive
21–26 Apr
4.86 out of 5 average rating, 42 reviews
Guest favourite
Home in Ramrod Key
Canalfront 3BD/2BA|FLKeys|POOL|DOCK
10-min drive
6–11 Mar
5.0 out of 5 average rating, 6 reviews
Cottage in Cudjoe Key
VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
12-min drive
20–25 Apr
4.61 out of 5 average rating, 92 reviews
Superhost
Cottage in Cudjoe Key
OCEANIA... water front cottage retreat ~
11-min drive
29 Apr – 4 May
4.83 out of 5 average rating, 84 reviews
Superhost
Home in Cudjoe Key
Newly Renovated Oceanside House with Pool
10-min drive
21–26 May
4.88 out of 5 average rating, 189 reviews
Guest favourite
Guest suite in Big Pine Key
Old Island Life
16-min drive
28 Apr – 3 May
4.87 out of 5 average rating, 471 reviews
Guest favourite
Home in Cudjoe Key
Paradise in Cudjoe! Perfect Family Home!
10-min drive
4–9 Oct
5.0 out of 5 average rating, 22 reviews
Home in Big Pine Key
Nature's Paradise-Ingrd Pool-Great Monthly Rental$
25-min drive
15–22 May
Superhost
Home in Cudjoe Key
Island Oasis ~ YOUR Paradise Awaits!
12-min drive
21–26 Apr
4.87 out of 5 average rating, 70 reviews
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
12-min drive
19–24 May
4.73 out of 5 average rating, 37 reviews
Superhost
Home in Cudjoe Key
Venture Out- Million Dollar Island Resort
11-min drive
20–25 Apr
5.0 out of 5 average rating, 7 reviews
Guest favourite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
12-min drive
17–22 Jul
4.91 out of 5 average rating, 77 reviews
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
10-min drive
18–23 May
4.78 out of 5 average rating, 74 reviews