Windward Side Resorts
1 Bedroom
1 Bathroom
Family Friendly
Resort
- Hot Tub
- Pool
- Balcony/Terrace
AU $370/Night
For 7 Nights AU $2,588
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
AU $1,463/Night
For 7 Nights AU $10,243
161.46 ft²
4 Guests
7 Bedrooms
2 Bathrooms
Ocean View
Hotel
- Oceanfront
- Pool
- Ocean View
AU $180/Night
For 7 Nights AU $1,257
AU $138/Night
For 7 Nights AU $963
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
AU $1,115/Night
For 7 Nights AU $7,803
362.38 ft²
7 Guests
27 Bedrooms
3 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Pool
- Ocean View
AU $207/Night
For 7 Nights AU $1,449
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Balcony/Terrace
- Child Friendly
- Laundry
AU $152/Night
For 7 Nights AU $1,061
4 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $620/Night
For 7 Nights AU $4,337
AU $187/Night
For 7 Nights AU $1,307
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
AU $358/Night
For 7 Nights AU $2,503
AU $1,465/Night
For 7 Nights AU $10,259
938 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $274/Night
For 7 Nights AU $1,915
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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:
- Haiku House, an amazing wooden villa situated in a tropical forest
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
- El Momo Cottages
- Saba Arawak Hotel
- El Momo Cottages
- Saba Arawak Hotel
- Caribbean Elegance & Comfort
- Home a way from home in the Unspoiled queen of the Caribbean.
- Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
- 2023 Villa Fairview on Saba. Ultimate privacy.
2. How many Resorts are available in Windward Side?
Currently, the total number of properties listed by RBO in 2026 is over 1 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
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Pet Friendly
- Child Friendly
AU $642/Night
For 7 Nights AU $4,490
1500 ft²
4 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $580/Night
For 7 Nights AU $4,063
2900 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $550/Night
For 7 Nights AU $3,851
900 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Private Pool
- Pool
- Balcony/Terrace
AU $304/Night
For 7 Nights AU $2,128
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
AU $543/Night
For 7 Nights AU $3,800
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Child Friendly
AU $992/Night
For 7 Nights AU $6,941
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
AU $521/Night
For 7 Nights AU $3,648
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Child Friendly
AU $290/Night
For 7 Nights AU $2,027
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Air Conditioner
- Child Friendly
- Laundry
AU $239/Night
For 7 Nights AU $1,672
230 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $211/Night
For 7 Nights AU $1,479
