Upper South Side Summer Rentals, Cottages & Cabins

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

About Upper South Side Summer Rental on PickleTrip

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

There are a lot of options in Upper South Side. If you plan on staying in the Upper 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 Upper South Side:

In 2025, PickleTrip offers 191 summer rentals in or around Upper 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 Upper South Side is $445. Check the full list of summer accommodations in Upper South Side.
There are 191 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 Upper South Side that have a private or indoor pool:

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

Yes, We have 191 summer rental homes in Upper South Side and types of place to stay in Upper South Side include:

  • Vacation Homes: 191 available for rent
  • Villas: 191 Rentals available for rent
  • Holiday Apartments: 191 Rentals available for rent
  • Hotels with Suites: 191 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Upper 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 Upper South Side.