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  2. New York
  3. Head of the Harbor
  4. Beach Home Rentals

Head of the Harbor Beach House Rentals & Places to Stay

Find the best beach rentals in Head of the Harbor - We found 17 exact matches

About Head of the Harbor Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Head of the Harbor? PickleTrip™ features more than 17 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Head of the Harbor. Several of these vacation rentals in Head of the Harbor are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Head of the Harbor.

PickleTrip™ Offers 17 holiday homes and places to stay in Head of the Harbor. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Head of the Harbor Beach Rentals

There are a lot of options in Head of the Harbor. If you plan on staying in the Head of the Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Home Rentals in Head of the Harbor:

The average cost for a beach rental in Head of the Harbor is $1,166 per night. PickleTrip has a wide assortment of great beachfront homes near Head of the Harbor that would suit your needs.
Yes, we have 17 beach rentals with pools available in Head of the Harbor. Check our search bar to find a selection of vacation rentals available near Head of the Harbor.
Yes, here are the top beach rentals in Head of the Harbor that allow you to bring your pet:

See all pet-friendly beach rentals in Head of the Harbor on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Head of the Harbor to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 17 properties with private swimming pools or private homes with indoor pools in the Head of the Harbor area.
About 17 properties in Head of the Harbor boast of having access to hot tubs.