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Windward Side Summer Rentals, Cottages & Cabins

Book a Place to Stay in Windward Side for Your Summer Getaway

About Windward Side Summer Rental on SunSkiResorts

SunSki's selection of summer rentals in Windward Side promises the ideal setting for your next seasonal escape. We offer a diverse array of properties boasting enticing features such as private pools, indoor/outdoor swimming facilities, hot tubs, WiFi, beachfront access, and more. Whether you're journeying with family, friends, or a larger group, we have a rental perfectly tailored to your requirements.

Immerse yourself in the epitome of summer leisure in Windward Side with SunSki. Our summer rental accommodations are meticulously curated to ensure utmost comfort and relaxation. From chic condos and opulent resorts to charming villas, quaint bungalows, cozy cabins, RVs, and cottages, we present a spectrum of options to match your vacation vision. Discover your idyllic summer retreat with SunSki.

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Frequently Asked Questions About Windward Side Luxury Rentals

In 2026, SunSki offers 20 summer rentals in or around Windward 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 Windward Side is $321. Check the full list of summer accommodations in Windward Side.
There are 20 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with SunSkiResorts.

Yes, here are some popular summer holiday rentals in Windward Side that have a private or indoor pool:

Check all holiday rentals with a pool in Windward Side on SunSkiResorts.

Yes, We have 20 summer rental homes in Windward Side and types of place to stay in Windward Side include:

  • Vacation Homes: 20 available for rent
  • Villas: 20 Rentals available for rent
  • Holiday Apartments: 20 Rentals available for rent
  • Hotels with Suites: 20 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Windward 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 Windward Side.