Photo by Meghan Watters

Search Villas in Windward Side

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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 2 Villas in Windward Side with updated reviews, rates, and availability.

Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (68)
"The villa is even more beautiful than the pictures. The views and gardens are even more vibrant and incredible than we expected. We were amazed at the incredible construction and attention to detail in the house. The building itself looks like much of the wood work and interior is custom built and individually crafted. All appliances and appointments are top notch. The atmosphere is so peaceful. Overall the villa is airy, spacious, bright and with views into the infinity of the Caribbean. "
Spyglass is a Private Villa With 360 View Near Windwardside.
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
Outdoor pool

Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.

10.0 out of 10, Exceptional, (4)
"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!"
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windward Side

Flamboyant Cottage - Spectacular View & Pool
Exterior

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (38)
"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! "
Flamboyant Cottage - Spectacular View & Pool
Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (68)
"The villa is even more beautiful than the pictures. The views and gardens are even more vibrant and incredible than we expected. We were amazed at the incredible construction and attention to detail in the house. The building itself looks like much of the wood work and interior is custom built and individually crafted. All appliances and appointments are top notch. The atmosphere is so peaceful. Overall the villa is airy, spacious, bright and with views into the infinity of the Caribbean. "
Spyglass is a Private Villa With 360 View Near Windwardside.
Home a way from home in the Unspoiled queen of the Caribbean.
Exterior

Home a way from home in the Unspoiled queen of the Caribbean.

10.0 out of 10, Exceptional, (3)
"Excellent place to stay for a family with kids. The pool was perfect for the kids to use up some energy. And cool off after a hike or walking the hills. The beautiful breeze that enters the main bedroom is amazing and little need for the ac to be on. Will definitely recommend to others."
Home a way from home in the Unspoiled queen of the Caribbean.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.