A calm sea with a mountain in the distance.

Windward Side Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Windward Side vacation rentals

Outdoor dining

Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views

Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
Sint Eustatius
$221 nightly
The price is $232
Jun 28 - Jun 29
Total with taxes and fees
Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
Property grounds

Cozy 1-bedroom apartment in Sint Eustatius

Cozy 1-bedroom apartment in Sint Eustatius
Sint Eustatius
$134 nightly
The price is $147
Jun 28 - Jun 29
Total with taxes and fees
Cozy 1-bedroom apartment in Sint Eustatius
Property grounds

Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad

Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Oranjestad
$183 nightly
The price is $189
Jul 3 - Jul 4
Total with taxes and fees
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Property grounds

Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad

Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Oranjestad
7.0 out of 10, Good, (2 reviews)
"The appartment is spacious and has everything you need. It was very neat and clean and the host Davon fast in response. The location is a quiet neighbourhood, not far away from the center. Thanks for having us. "
Netherlands
sytske m.
$183 nightly
The price is $189
Jul 3 - Jul 4
Total with taxes and fees
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Property grounds

2-bedroom apartment in St. Eustatius - Home away from Home

2-bedroom apartment in St. Eustatius - Home away from Home
St. Eustatius
$169 nightly
The price is $185
Jun 28 - Jun 29
Total with taxes and fees
2-bedroom apartment in St. Eustatius - Home away from Home
Front of property

Palm Spring Inn

Palm Spring Inn
3.0 star property
Oranjestad
8.4 out of 10, Very Good, (15 reviews)
"Really convenient for the airport ... But slightly further from town than expect.. Some upgrading work happening so roof top barbeque area not accessible and some noise . However room clean and large kitchen area if needed. Everyone really helpful. "
United Kingdom
lucy
$150 nightly
The price is $160
Jun 28 - Jun 29
Total with taxes and fees
Palm Spring Inn
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.
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Top Windward Side Hotel Reviews

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel

10/10 Excellent
"Staying at Quill Gardens felt like an extension of home. There wasn't anything that we didn't like. Marisol and Anthon were the best hosts."
Elaine 2-night trip
Posted 5 days ago
Quill Gardens Boutique Hotel

Find out more about Windward Side

Everything you need to know about Windward Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windward Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windward Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windward Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windward Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windward Side rentals

At Expedia, we put the best Windward Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windward Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windward Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windward Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windward Side?

Yes, we give you a choice of vacation rentals near top local attractions in Windward Side, or you can go with a more secluded option if you're looking for a relaxing stay. Windward Side is known for its seaside and mountain views.

What are some of the best vacation rentals that Windward Side has to offer?

Beautiful Traditional Saba Cottage With all the Modern Amenities: This Windward Side vacation home rental is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly. Another good choice for your trip to Windward Side is Home a way from home in the Unspoiled queen of the Caribbean..

How many vacation rentals are there in Windward Side?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Windward Side stay.

What’s there to see and do in Windward Side?

Cultural attractions include Dutch Museum of Saba and Saba Heritage Center, whereas Mt Scenery is one spot to enjoy nature. Other places in town to visit include Harry L Johnson Museum and Jo Bean Glass Art Studio.

What’s a vacation rental in Windward Side like?

A vacation rental is a private property where you can stay for several days or longer in Windward Side. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.