Cottage
10.0(103 Reviews)
1 Bedroom
2 Guests
Private Pool
Oceanfront
Parking
Pool
US $445/Night
7 Nights - US $3,117
Windward Villa Rentals
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Compare Villas, Resorts, & Rentals in Windward
10.0
US $1,124/Night
7 Nights - US $7,867
US $2,287/Night
7 Nights - US $16,012
Villa
10.0(55 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
Balcony/Terrace
US $597/Night
7 Nights - US $4,179
Villa
10.0(1 Review)
3 Bedrooms
6 Guests
Breakfast- Parking
- Pool
- Balcony/Terrace
US $1,458/Night
7 Nights - US $10,208
Villa
10.0(28 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
Skiing- Balcony/Terrace
US $813/Night
7 Nights - US $5,688
Villa
10.0(27 Reviews)
4 Bedrooms
9 Guests
- Private Pool
Hot Tub- Pool
- Skiing
US $1,780/Night
7 Nights - US $12,459
Apartment
10.0(25 Reviews)
1 Bedroom
2 Guests
- Balcony/Terrace
View
Kitchen
Air Conditioner
US $269/Night
7 Nights - US $1,883
Villa
10.0(21 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $1,170/Night
7 Nights - US $8,193
Luxury Places to Stay in Windward
Over 3677+ Luxury Places to Stay in or Near Windward
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Villa
6 Bedrooms
12 Guests
- Private Pool
- Pool
Ocean View- Balcony/Terrace
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Villa
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
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Villa
4 Bedrooms
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
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Top-Rated Villas with a Pool in Windward
Over 3423+ Top-Rated Private Villas with a Pool in or Near Windward
Villa
10.0(16 Reviews)
7 Bedrooms
14 Guests
- Private Pool
- Breakfast
- Parking
- Pool
US $1,002/Night
7 Nights - US $7,014
Villa
10.0(13 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,735/Night
7 Nights - US $12,148
Villa
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,026/Night
7 Nights - US $7,185
Villa
10.0(12 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $3,149/Night
7 Nights - US $22,045
Villa
10.0(11 Reviews)
1 Bedroom
3 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $963/Night
7 Nights - US $6,741
Villa
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $805/Night
7 Nights - US $5,633
Villa
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $1,335/Night
7 Nights - US $9,347
Villa
10.0(10 Reviews)
5 Bedrooms
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,235/Night
7 Nights - US $8,648
Villa
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $975/Night
7 Nights - US $6,822
Pet-Friendly Villas in Windward
Over 419+ Pet-Friendly Private Villas in or Near Windward
Villa
10.0(9 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,961/Night
7 Nights - US $13,727
Villa
10.0(1 Review)
4 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $1,185/Night
7 Nights - US $8,295
Villa
10.0(1 Review)
1 Bedroom
- Air Conditioner
Internet
Pet Friendly
Child Friendly
US $1,467/Night
7 Nights - US $10,266
Villa
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $1,349/Night
7 Nights - US $9,445
House
9.6(11 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $254/Night
7 Nights - US $1,777
US $1,329/Night
7 Nights - US $9,300
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $973/Night
7 Nights - US $6,811
Villa
10.0(1 Review)
5 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $5,596/Night
7 Nights - US $39,169
Large Private Villas in Windward
Over 3255+ Large Villas in or Near Windward for Groups and Families
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $879/Night
7 Nights - US $6,155
Villa
9.8(16 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $990/Night
7 Nights - US $6,929
US $4,909/Night
7 Nights - US $34,363
Villa
10.0(5 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $793/Night
7 Nights - US $5,550
Villa
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,319/Night
7 Nights - US $9,232
Villa
10.0(4 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,117/Night
7 Nights - US $7,816
US $891/Night
7 Nights - US $6,234
Villa
10.0(4 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $777/Night
7 Nights - US $5,439
Wheelchair Accessible Holiday Homes in Windward
Over 66+ Wheelchair Accessible Villas and Holiday Homes in or Near Windward
Villa
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,653/Night
7 Nights - US $11,570
US $1,301/Night
7 Nights - US $9,110
US $2,302/Night
7 Nights - US $16,115
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Hotel
9.7(22 Reviews)
Private Beach- Oceanfront
- Breakfast
EV Charge Station
US $1,386/Night
7 Nights - US $9,700
Villa
6 Bedrooms
12 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
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Villa
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
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Villa
5 Bedrooms
10 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
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Villa
4 Bedrooms
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
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Windward Villas, Airbnb and Holiday Homes Under $200
Over 2+ Windward Private Villas, Airbnb and Holiday Homes Under $200
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $194/Night
7 Nights - US $1,359
House
1 Bedroom
2 Guests
- Child Friendly
Sports/Activities
Designated Smoking Area
US $114/Night
7 Nights - US $796
Instantly Bookable Villa Rentals in Windward
Over 968+ Instantly Bookable Private Villas in or Near Windward
House
10.0(15 Reviews)
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $245/Night
7 Nights - US $1,718
Villa
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,631/Night
7 Nights - US $11,419
House
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $471/Night
7 Nights - US $3,299
Villa
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $3,191/Night
7 Nights - US $22,339
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $3,022/Night
7 Nights - US $21,154
Villa
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,684/Night
7 Nights - US $18,785
Villa
10.0(3 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,684/Night
7 Nights - US $18,785
Villa
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,303/Night
7 Nights - US $9,124
Villa
10.0(3 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,303/Night
7 Nights - US $9,124
Book a Last Minute Place to Stay in Windward
About Windward Vacation Rentals
There are more than 3686 incredible getaway rentals that are available in Windward. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windward.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windward, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windward. Places to stay near Windward are 1126.59 ft² on average, with prices averaging US $4,385 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windward. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Windward, BL
There are 17 hotels in Windward and 3661 rentals
- Prices for a holiday home in Windward start at US $245
- Top rated vacation home in Windward is Fabulous stay in modern Villa – Surrounded by nature. Special Offer
- Most popular short term in Windward is Christopher Hotel
- Cheapest place to stay in Windward is Bungalow CAZ A Saline N°2
- Most expensive holiday rental in Windward is Beautiful Neo Luxury villa
Recently Booked Hotels, Resorts, or Rentals in Windward
Frequently Asked Questions About Windward?
What are the top hotels or resorts in Windward?
We provide an array of great vacation destinations in Windward. If you are looking to stay in or around the Windward area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windward:
- Fabulous stay in modern Villa – Surrounded by nature. Special Offer
- Hotel Les Ondines Sur La Plage
- BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
- Villa Tiwa 2 Bed-2 Bath Pointe Milou
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- grand appartement, vue ocean
- Amazing swimming pool. La Roche dans l'Eau.
- Lagon Jaune, amazing sea view, direct owner, credit card, 3 or 4 bedrooms rate
- Bungalow CAZ A Saline N°2
- Villa Roy - Lagoon & Ocean Breathtaking View
How many vacation rentals have private pools in Windward?
We have 2794 luxury villas and vacation rentals featuriung a private pool in and near Windward. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Windward is best for families?
Searching for a family-friendly getaway in Windward? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Windward?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 3686 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windward.
