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Wailea Summer Rentals, Cottages & Cabins

Book a Place to Stay in Wailea for Your Summer Getaway

About Wailea Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Wailea 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 Wailea 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 Wailea Luxury Rentals

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

In 2025, PickleTrip offers 1830 summer rentals in or around Wailea. 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 Wailea is $1,025. Check the full list of summer accommodations in Wailea.
There are 1830 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 Wailea that have a private or indoor pool:

Check all holiday rentals with a pool in Wailea on PickleTrip.

Yes, We have 1830 summer rental homes in Wailea and types of place to stay in Wailea include:

  • Vacation Homes: 1830 available for rent
  • Villas: 1830 Rentals available for rent
  • Holiday Apartments: 1830 Rentals available for rent
  • Hotels with Suites: 1830 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Wailea. 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 Wailea.