Photo by Meghan Watters

Search Villas in Windward Side

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

7 Saf. - 9 Saf.

In two weeks

14 Saf. - 16 Saf.

In one month

28 Saf. - 2 Rab. I

In two months

28 Rab. I - 30 Rab. I

Compare Villas in Windward Side with updated reviews, rates, and availability.

"We loved it here so much, we already booked it for Christmas next year. nuff said. "

"Our stay was fantastic! Cece was awesome and helpful in every way! She arranged a rental car for us at the house so we could get around the island independently. Views were magnificent and hacienda was perfect! Very clean with every amenity you could possibly want! Kitchen is fully stocked with anything you could possibly need to cook a meal. Don’t hesitate to book this magnificent home! You won’t be sorry!"

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windward Side

"Our stay was perfect from the minute we landed on the island. Easy communication with property manager, taxi prearranged and the cottage had everything we needed! Great views, walking distance to town, restaurants and hiking. Everyone we met was SUPER friendly which made our stay extra special! "