Windward Side Villa Rentals & Resorts

Find villas near Windward Side - We found 7 exact matches

About Windward Side Villa on Casai.com

Casai boasts more than 7 an exceptional array of private villas near Windward Side. These opulent rentals epitomize luxury living, offering exclusive amenities such as private swimming pools, Wi-Fi, spas, hot tubs, and more.

Discover a diverse selection of villa rentals near Windward Side with Casai, catering to families, friends, and couples seeking indulgence and seclusion. Whether you desire a unique architectural style or a specific size, our collection of luxury villas ensures that every preference is met.

Embark on an unforgettable retreat with Casai's exclusive rental villas, each meticulously curated to offer an unparalleled experience. From secluded beachfront escapes to majestic mountainside havens, our all-in-one travel platform matches you with the perfect private villa in Windward Side for your dream vacation. Revel in lavish amenities such as private pools, sumptuous bedrooms, and additional features like tennis courts, beach volleyball, spas, fitness clubs, and beyond.

Experience the epitome of luxury with Casai's private villas, available for last-minute bookings and often accompanied by special offers for Airbnb, VRBO, and Casai-style villas. Explore your last-minute getaway today with Casai in Windward Side, and prepare to bask in the utmost comfort and sophistication on your next holiday.

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Frequently Asked Questions About Windward Side Rental Villas

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

At Casai.com, the average rental fee for standard villas in Windward Side is $523 per night. Casai has a large database of quality villas near Windward Side 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 Side that are pet friendly:See all pet-friendly vacation rentals in Windward Side on Casai.com
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 Side to find what works for you.
Based on the 2025 data from our Casai.com site, there are more than 7 private swimming pools or villas with indoor pools in or near Windward Side.
There are 7 villas in or near Windward Side that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Windward Side on Casai.com
Most definitely! There are many luxury villas in Windward Side. 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 Side.