Windward Islands Winter Rentals & Holiday Homes

Discover winter rentals Windward Islands - We found 184 exact matches

About Windward Islands Winter Rental on SunSkiResorts

Planning a winter vacation in Windward Islands? Discover 184 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Windward Islands perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Windward Islands start at US $289. The most popular properties in Windward Islands include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Windward Islands, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Windward Islands and unlock incredible deals.

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Frequently Asked Questions About Windward Islands Winter Rentals

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

The average cost for winter rentals in Windward Islands is $289 per night. SunSki has a wide list of great winter places to stay near Windward Islands that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Windward Islands that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Windward Islands on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Windward Islands to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 184 private swimming pools or indoor pools accommodations near Windward Islands along with other great amenities.

About 184 holiday rentals in Windward Islands boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Windward Islands for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Windward Islands with all the best amenities for your next trip.