Windward Side Resorts
4 Bathrooms
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,540/Night
For 7 Nights US $24,782
612 ft²
19 Guests
7 Bathrooms
Free Cancellation
Resort
- Oceanfront
- Spa
- Fireplace/Heating
US $339/Night
For 7 Nights US $2,374
1 Bathroom
Family Friendly
Resort
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $333/Night
For 7 Nights US $2,328
US $255/Night
For 7 Nights US $1,788
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $770/Night
For 7 Nights US $5,390
753.47 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $255/Night
For 7 Nights US $1,783
US $110/Night
For 7 Nights US $773
1400 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
US $133/Night
For 7 Nights US $928
753.47 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Ocean View
US $250/Night
For 7 Nights US $1,750
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Parking
- Air Conditioner
US $264/Night
For 7 Nights US $1,849
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
US $81/Night
For 7 Nights US $567
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
US $208/Night
For 7 Nights US $1,456
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
Windward Side Resorts Frequently Asked Questions
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:
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
- Statia's best views, comfort, privacy, & nature on a world-class diving island!
- Quill Gardens Boutique Hotel
- Barrel House Suite St Eustatius
- Talk of the Town Inn & Suites
- The Beach House and 2 appartments for full or separate rental, all with a private beach
- Cattleya Flor Hotel
- El Momo Cottages
- A Quiet Getaway
- The Old Gin House
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
350.6 ft²
15 Guests
7 Bedrooms
7 Bathrooms
Group Friendly
House
- Balcony/Terrace
- View
- Breakfast
US $148/Night
For 7 Nights US $1,036
6 Guests
2 Bedrooms
1 Bathroom
Apartment
- Air Conditioner
- Internet
- Child Friendly
US $199/Night
For 7 Nights US $1,394
376.74 ft²
4 Guests
8 Bedrooms
2 Bathrooms
Free Cancellation
Cabin
- Pool
- Balcony/Terrace
- View
US $105/Night
For 7 Nights US $735
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
US $160/Night
For 7 Nights US $1,123
10763.91 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Parking
- Air Conditioner
US $295/Night
For 7 Nights US $2,065
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
US $160/Night
For 7 Nights US $1,123
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- View
- Kitchen
US $86/Night
For 7 Nights US $603
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
US $1,011/Night
For 7 Nights US $7,076
4 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $428/Night
For 7 Nights US $2,996
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
US $247/Night
For 7 Nights US $1,729
938 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $189/Night
For 7 Nights US $1,323
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Pet Friendly
- Child Friendly
US $443/Night
For 7 Nights US $3,102
