Windward Villa Rentals & Ski-in/Ski-out Homes

Find villas near Windward - We found 142 exact matches

About Windward Villa on SunSkiResorts

Explore a plethora of luxury villas offered by SunSki in the Windward area. These rentals boast top-notch amenities like private swimming pools, WiFi, hot tubs, and more, ensuring a comfortable and delightful stay.

Whether you're traveling with friends, family, or planning a romantic escape, SunSki provides a variety of villa options to suit your needs in the Windward area. Each rental features its own unique style and amenities.

SunSki's villas are situated in some of the most coveted destinations globally, including Windward. Whether you prefer a beachfront, mountain, or seaside retreat, SunSki offers a diverse range of options, many of which include private pools, luxurious bedrooms, and additional amenities like tennis courts and fitness clubs.

With SunSki, finding and booking last-minute villa rentals in Windward is effortless. Browse our selection of villas and seize special offers and deals on SunSki as well as other leading vacation rental platforms such as Airbnb and VRBO. Make your next holiday truly memorable with SunSki.

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Frequently Asked Questions About Windward Rental Villas

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

At SunSkiResorts, the average rental fee for standard villas in Windward is $330 per night. SunSki has a large database of quality villas near Windward that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Windward that are pet friendly:See all pet-friendly vacation rentals in Windward on SunSkiResorts
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Windward to find what works for you.
Based on the 2025 data from our SunSkiResorts site, there are more than 142 private swimming pools or villas with indoor pools in or near Windward.
There are 142 villas in or near Windward that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Windward on SunSkiResorts
Most definitely! There are many luxury villas in Windward. Use our search filter to discover all of our luxury villas, and choose the one that matches your taste. Sorting by price is another way to find the most expensive villas in Windward.