Head of The Bay Summer Rentals, Cottages & Cabins

Book a Place to Stay in Head of The Bay for Your Summer Getaway

About Head of The Bay Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Head of The Bay are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Head of The Bay with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Head of The Bay Luxury Rentals

In 2025, PickleTrip offers 118 summer rentals in or around Head of The Bay. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Head of The Bay is $1,155. Check the full list of summer accommodations in Head of The Bay.
There are 118 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Head of The Bay that have a private or indoor pool:

Check all holiday rentals with a pool in Head of The Bay on PickleTrip.

Yes, We have 118 summer rental homes in Head of The Bay and types of place to stay in Head of The Bay include:

  • Vacation Homes: 118 available for rent
  • Villas: 118 Rentals available for rent
  • Holiday Apartments: 118 Rentals available for rent
  • Hotels with Suites: 118 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Head of The Bay. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Head of The Bay.