Near South Side Summer Rentals, Cottages & Cabins

Book a Place to Stay in Near South Side for Your Summer Getaway

About Near South Side Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Near South Side 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 Near South Side 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 Near South Side Luxury Rentals

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

In 2026, PickleTrip offers 304 summer rentals in or around Near South Side. 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 Near South Side is $378. Check the full list of summer accommodations in Near South Side.
There are 304 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 Near South Side that have a private or indoor pool:

Check all holiday rentals with a pool in Near South Side on PickleTrip.

Yes, We have 304 summer rental homes in Near South Side and types of place to stay in Near South Side include:

  • Vacation Homes: 304 available for rent
  • Villas: 304 Rentals available for rent
  • Holiday Apartments: 304 Rentals available for rent
  • Hotels with Suites: 304 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Near South Side. 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 Near South Side.