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Search results; Over 1,000 homes in Cudjoe Key

Top guest favorite
Home in Cudjoe Key
Oceanfront with a dock, kayaks, and pool
2 bedrooms, 3 beds, 3 private baths
Aug 12 – 17
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4.94 out of 5 average rating, 33 reviews
Guest favorite
Home in Cudjoe Key
Oceanfront with a heated pool and dock
4.83 out of 5 average rating, 111 reviews, 5 bedrooms, 6 beds, 3 baths
Sep 26 – Oct 1
Guest favorite
Cottage in Cudjoe Key
Gated community with a saltwater pool
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 4 beds, 1 bath
Aug 15 – 20
Top guest favorite
Home in Cudjoe Key
Ocean-view cottage with a 52-foot dock
4.97 out of 5 average rating, 90 reviews, 2 bedrooms, 4 beds, 1 bath
Sep 13 – 18
Guest favorite
Home in Cudjoe Key
Waterfront home with a private dock
4.86 out of 5 average rating, 7 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 24 – 29
Top guest favorite
Home in Cudjoe Key
Waterfront villa with a pool and jacuzzi
4.97 out of 5 average rating, 29 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 23 – 28
Guest favorite
Home in Cudjoe Key
Waterfront with a kayak and lagoon
4.97 out of 5 average rating, 206 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 24 – 29
Guest favorite
Home in Cudjoe Key
Heated pool with Atlantic Ocean views
4.88 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 7 – 12
Guest favorite
Home in Big Pine Key
220-foot dock with open-water views
4.91 out of 5 average rating, 102 reviews, 3 bedrooms, 3 beds, 4 baths
Oct 5 – 10
Superhost
Villa in Marathon
On the water in a private marina
4.86 out of 5 average rating, 602 reviews, 1 bedroom, 2 beds, 1 bath
Aug 17 – 22
Top guest favorite
Home in Cudjoe Key
Waterfront with a dock and boat slip
4.94 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 12 – 17
Guest favorite
Home in Summerland Key
Waterfront with boat basin and ramp
4.93 out of 5 average rating, 127 reviews, 3 bedrooms, 6 beds, 1 bath
Aug 22 – 27
Guest favorite
Home in Cudjoe Key
Canal-front stilt home with dock and kayaks
4.93 out of 5 average rating, 96 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Guest favorite
Home in Cudjoe Key
Waterfront with a dock and ocean access
4.89 out of 5 average rating, 18 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 15 – 22
Guest favorite
Cottage in Cudjoe Key
Waterfront with a 35’ dock and kayaks
4.84 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 31 – Sep 5
Home in Cudjoe Key
Canal-front cottage with a 35’ seawall
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 5 beds, 2 baths
Aug 13 – 18
Guest favorite
Houseboat in Marathon
Houseboat anchored in the mangroves
4.92 out of 5 average rating, 90 reviews, 1 bedroom, 1 bed, 1 bath
Sep 27 – Oct 2
Guest favorite
Home in Cudjoe Key
Waterfront with a 35-foot seawall
4.89 out of 5 average rating, 157 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 12 – 17
Guest favorite
Houseboat in Key West
Off-grid floating bungalow in Key West
4.91 out of 5 average rating, 557 reviews, 1 bedroom, 1 bed, 1 bath
Aug 18 – 23