Head of The Bay Beach House Rentals & Places to Stay

Find the best beach rentals in Head of The Bay - We found 70 exact matches

About Head of The Bay Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Head of The Bay? PickleTrip™ features more than 70 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Head of The Bay. Several of these vacation rentals in Head of The Bay 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 Bay.

PickleTrip™ Offers 70 holiday homes and places to stay in Head of The Bay. 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 Bay Beach Rentals

The average cost for a beach rental in Head of The Bay is $1,395 per night. PickleTrip has a wide assortment of great beachfront homes near Head of The Bay that would suit your needs.
Yes, we have 70 beach rentals with pools available in Head of The Bay. Check our search bar to find a selection of vacation rentals available near Head of The Bay.
Yes, here are the top beach rentals in Head of The Bay that allow you to bring your pet:

See all pet-friendly beach rentals in Head of The Bay 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 Bay to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 70 properties with private swimming pools or private homes with indoor pools in the Head of The Bay area.
About 70 properties in Head of The Bay boast of having access to hot tubs.