Compare Windward Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Windward

BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This villa also has a garden.
Pool
Kitchen
Brand new boutique villa in les Hauts de Saint Jean with stunning Eden Rock view

Brand new boutique villa in les Hauts de Saint Jean with stunning Eden Rock view

This villa features an outdoor pool and laundry facilities.
Pool
Kitchen
Villa Dreamtime ideal Family and Friends / 2 BDR

Villa Dreamtime ideal Family and Friends / 2 BDR

Guests staying at this villa enjoy a hot tub, laundry facilities, and a garden. Friendly staff can provide concierge services, and also offer advice about sightseeing. Additional amenities include barbecue grills and a water dispenser.
Pool
Hot Tub
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This beach villa also has a garden.
Pool
Kitchen
Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

Guests of this villa enjoy a hot tub, an arcade/game room, and local meal delivery service. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this family-friendly villa include barbecue grills and a garden.
Pool
Hot Tub
Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Villa Yvantino beachfront ( 2 bedroom )

Villa Yvantino beachfront ( 2 bedroom )

Guests of this villa have access to a hot tub.
Hot Tub
Pet friendly
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills. Staff members can help with accommodation requests, and provide concierge services.
Pool
Kitchen
Traditional Caribbean Style house with breathtaking views

Traditional Caribbean Style house with breathtaking views

This villa is a smoke-free villa.
Pet friendly
Air conditioning
Don't see what you're looking for?
See all available properties in Windward
View all properties
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.

Luxury Villas

Book luxury villas in Windward
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Windward. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Windward, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Windward
You won’t have a problem finding your own space in Windward. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Windward on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Windward rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Windward Villas essential information

Accommodation
727 Villas
Lowest Price
Highest Price
Popular accommodation
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach, Brand new boutique villa in les Hauts de Saint Jean with stunning Eden Rock view, Villa Dreamtime ideal Family and Friends / 2 BDR, St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive, Spacious Luxury 4 bedrooms, direct no agencies, fully renovated, Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat, Villa Yvantino beachfront ( 2 bedroom ), ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING, Traditional Caribbean Style house with breathtaking views

More Places To Stay in Windward

All Accommodation Types