Highland Hills Summer Rentals, Cottages & Cabins

Book a Place to Stay in Highland Hills for Your Summer Getaway

About Highland Hills Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Highland Hills 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 Highland Hills 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 Highland Hills Luxury Rentals

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

In 2026, PickleTrip offers 131 summer rentals in or around Highland Hills. 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 Highland Hills is $290. Check the full list of summer accommodations in Highland Hills.
There are 131 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 Highland Hills that have a private or indoor pool:

Check all holiday rentals with a pool in Highland Hills on PickleTrip.

Yes, We have 131 summer rental homes in Highland Hills and types of place to stay in Highland Hills include:

  • Vacation Homes: 131 available for rent
  • Villas: 131 Rentals available for rent
  • Holiday Apartments: 131 Rentals available for rent
  • Hotels with Suites: 131 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Highland Hills. 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 Highland Hills.