Cutthroat Harbor Estates holiday homes
We found 309 holiday rentals — enter your dates for availability
Discover a selection of 71 homes and other holiday rentals in Cutthroat Harbor Estates that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
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Find the best place to stay - Cutthroat Harbor Estates

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.4 out of 10
very good
(118 reviews)
Top rated rentals - Cutthroat Harbor Estates

Everything you’d want in a rental!
10 out of 10
exceptional
(25 reviews)
We stayed for a month in this beautiful house. It was well-stocked beyond any house we have rented. Everything you’d need to cook, clean, and have fun! Adel was very easy to work with and very responsive when we had a question during our stay. The bay is very shallow so be aware if you want to rent a boat. You must know how to navigate the shallow areas to gain access to the Atlantic or Gulf, but it’s possible and simple once you know the channels. We look forward to renting this house again in the future!
Jamie S.
Stayed Jun 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value





