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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Windward Side vacation rentals

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
The price is AED 528
AED 586 total
includes taxes & fees
3 Jul - 4 Jul
Palm Spring Inn
Property grounds

Cozy 1-bedroom apartment in Sint Eustatius

Cozy 1-bedroom apartment in Sint Eustatius
Sint Eustatius
The price is AED 420
AED 539 total
includes taxes & fees
3 Jul - 4 Jul
Cozy 1-bedroom apartment in Sint Eustatius
Property grounds

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

2-bedroom apartment in St. Eustatius - Home away from Home
St. Eustatius
The price is AED 545
AED 679 total
includes taxes & fees
3 Jul - 4 Jul
2-bedroom apartment in St. Eustatius - Home away from Home
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
The price is AED 606
AED 853 total
includes taxes & fees
8 Jul - 9 Jul
Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
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.
The price is AED 588
AED 696 total
includes taxes & fees
9 Jul - 10 Jul
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Property grounds

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

Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Oranjestad
The price is AED 588
AED 696 total
includes taxes & fees
9 Jul - 10 Jul
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
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

Talk of the Town Inn & Suites

Talk of the Town Inn & Suites

8/10 Good
"The room was nice, clean spacious but did not have a TV . Nice kitchen.The location is good , near the airport"
ARIEH 2-night trip
Posted 5 days ago
Talk of the Town Inn & Suites

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.