Head of the Harbor Summer Rentals, Cottages & Cabins

Book a Place to Stay in Head of the Harbor for Your Summer Getaway

About Head of the Harbor Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Head of the Harbor 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 Harbor 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™.

Show more
Show less

Frequently Asked Questions About Head of the Harbor Luxury 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 Summer Rentals in Head of the Harbor:

In 2025, PickleTrip offers 67 summer rentals in or around Head of the Harbor. 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 Harbor is $750. Check the full list of summer accommodations in Head of the Harbor.
There are 67 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 Harbor that have a private or indoor pool:

Check all holiday rentals with a pool in Head of the Harbor on PickleTrip.

Yes, We have 67 summer rental homes in Head of the Harbor and types of place to stay in Head of the Harbor include:

  • Vacation Homes: 67 available for rent
  • Villas: 67 Rentals available for rent
  • Holiday Apartments: 67 Rentals available for rent
  • Hotels with Suites: 67 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Head of the Harbor. 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 Harbor.