Windward Side Resorts
Resort
4 Baths
Fireplace/Heating
Pool
Balcony/Terrace
Breakfast
CA $4,967/Night
7 Nights - CA $34,772
Resort
9.3(76 Reviews)
7 Baths
19 Guests
612 ft²
Oceanfront
Spa- Fireplace/Heating
- Pool
CA $476/Night
7 Nights - CA $3,331
Resort
9.8(7 Reviews)
1 Bath
- Balcony/Terrace
Kitchen
Air Conditioner
Child Friendly
CA $467/Night
7 Nights - CA $3,266
Resort
5.8(11 Reviews)
1 Bath
Hot Tub- Pool
- Balcony/Terrace
- Air Conditioner
CA $358/Night
7 Nights - CA $2,509
Apartment
1 Bedroom
1 Bath
2 Guests
Ocean View
View- Kitchen
- Child Friendly
CA $121/Night
7 Nights - CA $846
Apartment
9.4(14 Reviews)
1 Bedroom
1 Bath
2 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $357/Night
7 Nights - CA $2,502
House
8.6(9 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Air Conditioner
Laundry
CA $199/Night
7 Nights - CA $1,389
Villa
10.0(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
Private Pool- Pool
- Ocean View
- Balcony/Terrace
CA $1,418/Night
7 Nights - CA $9,929
House
9.0(8 Reviews)
3 Bedrooms
3 Baths
3 Guests
753.47 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $351/Night
7 Nights - CA $2,455
Villa
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,080/Night
7 Nights - CA $7,563
Apartment
8.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
Parking- Air Conditioner
Internet
CA $114/Night
7 Nights - CA $796
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $475/Night
7 Nights - CA $3,327
People Visiting Windward Side Also Like
Why Choose Rent By Owner for your Windward Side Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windward Side
How to Book Your Windward Side Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windward Side
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Windward Side
Harry L Johnson Museum
Jo Bean Glass Art Studio
Dutch Museum of Saba
Mt Scenery
Frequently Asked Questions About Windward Side Resorts
1. What are the top Resorts in Windward Side?
There are a lot of options in Windward Side. If you plan on staying in the Windward Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Windward Side:
2. How many Resorts are available in Windward Side?
Currently, the total number of properties listed by RBO in 2026 is over 4 in the Windward Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Windward Side.
More Rentals You May Like Near Windward Side
Apartment
7.8(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
656.6 ft²
- Balcony/Terrace
- View
- Breakfast
Pet Friendly
CA $186/Night
7 Nights - CA $1,304
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $186/Night
7 Nights - CA $1,302
House
7.6(59 Reviews)
7 Bedrooms
7 Baths
15 Guests
350.6 ft²
- Balcony/Terrace
- View
- Breakfast
- Parking
CA $213/Night
7 Nights - CA $1,493
Apartment
7.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
CA $264/Night
7 Nights - CA $1,851
Cabin
7.5(69 Reviews)
8 Bedrooms
2 Baths
4 Guests
376.74 ft²
- Pool
- Balcony/Terrace
- View
- Pet Friendly
CA $147/Night
7 Nights - CA $1,031
Villa
5.0(2 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $601/Night
7 Nights - CA $4,204
House
5.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
CA $347/Night
7 Nights - CA $2,426
Cottage
5.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
938 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $265/Night
7 Nights - CA $1,856
Villa
5.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Pet Friendly
- Child Friendly
CA $622/Night
7 Nights - CA $4,353
Villa
4.9(59 Reviews)
3 Bedrooms
3 Baths
4 Guests
1500 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $563/Night
7 Nights - CA $3,939
Villa
4.9(9 Reviews)
5 Bedrooms
5 Baths
12 Guests
2900 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $533/Night
7 Nights - CA $3,732
Cottage
4.8(27 Reviews)
2 Bedrooms
2 Baths
4 Guests
900 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $295/Night
7 Nights - CA $2,063
