Pool, Parking, Air Conditioner, Internet, Security/Safety, Fireplace/Heating, Child Friendly
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
2 reviews
Hot Tub, Kitchen, Pool, Air Conditioner, Pet Friendly, Parking, Breakfast
Very Good
3 reviews
AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry
Very Good
135 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
Superb
10 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Very Good
101 reviews
Luxury, Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
Superb
2 reviews
AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub
Very Good
136 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
Exceptional
3 reviews
Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Pool
Exceptional
3 reviews
Parking, Kitchen, Air Conditioner, Internet, Pool, Child Friendly
AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer
Pool, Laundry, Kitchen, Pet Friendly, View, Air Conditioner, Balcony/Terrace
Fabulous
5 reviews
AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
1 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking
Exceptional
2 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Review score
2 reviews
Balcony/Terrace, Pool, Kitchen, Internet, Air Conditioner, Pet Friendly, Parking
Exceptional
5 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
14 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry
Exceptional
57 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave
AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer
Exceptional
1 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
11 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
67 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry
Exceptional
2 reviews
Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Villa Rentals in Windward.
VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
Some of the best villa rentals in Windward are:
You can currently explore 209 verified villa rentals in Windward. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.
Villa prices in Windward vary depending on the season, location, and amenities. Rates typically start from around $151 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.
Many villas in Windward are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Windward.
Yes, Windward offers a wide range of villas ideal for group stays. Many properties include 1 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.
For popular travel periods, it’s generally recommended to book your Windward villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.
Villas in Windward often include highly sought-after amenities such as Balcony/Terrace, Laundry, and Pool. These features enhance comfort and convenience, making them especially popular among travelers visiting Windward.
To discover top-rated villas in Windward, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.