Cleveland Park Summer Rentals, Cottages & Cabins

Book a Place to Stay in Cleveland Park for Your Summer Getaway

About Cleveland Park Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Cleveland Park 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 Cleveland Park 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 Cleveland Park Luxury Rentals

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

In 2025, PickleTrip offers 628 summer rentals in or around Cleveland Park. 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 Cleveland Park is $404. Check the full list of summer accommodations in Cleveland Park.
There are 628 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 Cleveland Park that have a private or indoor pool:

Check all holiday rentals with a pool in Cleveland Park on PickleTrip.

Yes, We have 628 summer rental homes in Cleveland Park and types of place to stay in Cleveland Park include:

  • Vacation Homes: 628 available for rent
  • Villas: 628 Rentals available for rent
  • Holiday Apartments: 628 Rentals available for rent
  • Hotels with Suites: 628 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Cleveland Park. 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 Cleveland Park.