Olive Square Summer Rentals, Cottages & Cabins

Book a Place to Stay in Olive Square for Your Summer Getaway

About Olive Square Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Olive Square 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 Olive Square 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 Olive Square Luxury Rentals

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

In 2025, PickleTrip offers 398 summer rentals in or around Olive Square. 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 Olive Square is $486. Check the full list of summer accommodations in Olive Square.
There are 398 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 Olive Square that have a private or indoor pool:

Check all holiday rentals with a pool in Olive Square on PickleTrip.

Yes, We have 398 summer rental homes in Olive Square and types of place to stay in Olive Square include:

  • Vacation Homes: 398 available for rent
  • Villas: 398 Rentals available for rent
  • Holiday Apartments: 398 Rentals available for rent
  • Hotels with Suites: 398 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Olive Square. 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 Olive Square.