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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windward Side vacation rentals

A paved pathway flanked by palm trees and buildings with a clear sky above.

1. 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 ￥22,757
￥25,260 total
includes taxes & fees
Oct 12 - Oct 13
Palm Spring Inn
A paved pathway flanked by palm trees and buildings with a clear sky above.

2. Cozy 1-bedroom apartment in Sint Eustatius

Cozy 1-bedroom apartment in Sint Eustatius
Sint Eustatius
8.0 out of 10, Very good, (1 review)
The price is ￥18,095
￥23,251 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1-bedroom apartment in Sint Eustatius
A courtyard with a central paved area, surrounded by a white building with multiple floors and balconies.

3. 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 ￥25,330
￥29,984 total
includes taxes & fees
Oct 17 - Oct 18
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
A paved pathway flanked by palm trees and buildings with a clear sky above.

4. 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 ￥23,509
￥29,262 total
includes taxes & fees
Oct 12 - Oct 13
2-bedroom apartment in St. Eustatius - Home away from Home
An outdoor patio with a table and chairs, a wicker sofa, and a view of the ocean.

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

Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
Sint Eustatius
8.0 out of 10, Very good, (1 review)
The price is ￥25,711
￥36,377 total
includes taxes & fees
Oct 12 - Oct 13
Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
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

El Momo Cottages

El Momo Cottages

10/10 Excellent
"Fun little place to stay at Saba. Not a traditional hotel, but each room is in it's own little cabin basically in a jungle with a patio and a bathroom. The jungle gets surprisingly loud at night and the morning views from our cabin were stunning. There is a lot of stairs everywhere around the property, so you'll have to be comfortable carrying your luggage and climbing the stairs up and down. Swimming pool was a very nice touch after a long day of hiking."
Martina 2-night trip
Posted 1 day ago
El Momo Cottages

Find out more about Windward Side

Search for holiday rentals in Windward Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Windward Side using one of the methods below:

  • View our selection of featured holiday rentals in Windward Side
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Look no further and take a look at our great range of rental properties in Windward Side!

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?

Home a way from home in the Unspoiled queen of the Caribbean.: This Windward Side vacation home rental is located in the city center and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden. Another good choice for your trip to Windward Side is Beautiful Traditional Saba Cottage With all the Modern Amenities.

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 Harry L Johnson Museum, whereas Mt Scenery is one spot to enjoy nature. Other places in town to visit include Saba Heritage Center 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.