Windward Islands Cottage Rentals & Golf course

Find the best cottages in Windward Islands - We found 10 exact matches

About Windward Islands Cottage Rentals on StayAndPlay

Looking for exceptional golf cottages near Windward Islands for your next getaway? StayAndPlay offers more than 10 unique golf retreats and luxury villas, perfect for your family or group trip. Discover accommodations set in scenic golf destinations, featuring amenities like private pools, championship course access, and spacious living areas. These rentals provide an exceptional experience, catering to families, friends, couples, or golf enthusiasts.

Planning a golf retreat or a getaway for your group? StayAndPlay provides a variety of accommodations, including top-rated golf cottages, private villas, and spacious vacation rentals, connecting you directly with property owners to secure the best rates.

Explore 10 premium golf stays and exclusive golf-friendly accommodations in Windward Islands with StayAndPlay. Find unique Airbnb-style and VRBO-style golf rentals perfect for your weekend escape, golf vacation, or corporate retreat, all within your budget.

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Frequently Asked Questions About Windward Islands Rental Cottages

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 Cottage Rentals in Windward Islands:

The average cost for a cottage rental in Windward Islands is $179 per night. StayAndPlay.com has a wide list of great cottages near Windward Islands that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Windward Islands that allow you to bring your pet:

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

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windward Islands to find one that works for you.
As of 2026, the data from StayAndPlay shows that there are Over 10 private swimming pools or cottages with indoor pools in the Windward Islands area along with other great amenities.
About 10 cottages in Windward Islands boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Windward Islands on StayAndPlay
Yes, there are luxury cottages in Windward Islands. Find more luxury, lakefront, winter, & last-minute cottage rentals near Windward Islands.