Webster Square Summer Rentals, Cottages & Cabins

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

About Webster Square Summer Rental on PickleTrip

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

There are a lot of options in Webster Square. If you plan on staying in the Webster 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 Webster Square:

In 2025, PickleTrip offers 33 summer rentals in or around Webster 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 Webster Square is $238. Check the full list of summer accommodations in Webster Square.
There are 33 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 Webster Square that have a private or indoor pool:

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

Yes, We have 33 summer rental homes in Webster Square and types of place to stay in Webster Square include:

  • Vacation Homes: 33 available for rent
  • Villas: 33 Rentals available for rent
  • Holiday Apartments: 33 Rentals available for rent
  • Hotels with Suites: 33 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Webster 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 Webster Square.