View of Saba and Statia (Sint Eustatius) in the Dutch Caribbean from the north coast of Saint Kitts

Windward Side Holiday Rentals

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Check prices for these dates

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

Our top choices for Windward Side holiday 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
The price is HK$1,291
HK$1,817 total
includes taxes & fees
28 Jun - 29 Jun
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
The price is HK$896
HK$1,151 total
includes taxes & fees
26 Jun - 27 Jun
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
The price is HK$1,254
HK$1,477 total
includes taxes & fees
2 Jul - 3 Jul
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.
The price is HK$1,254
HK$1,477 total
includes taxes & fees
2 Jul - 3 Jul
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
The price is HK$1,164
HK$1,449 total
includes taxes & fees
26 Jun - 27 Jun
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
The price is HK$1,127
HK$1,251 total
includes taxes & fees
26 Jun - 27 Jun
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 4 days ago
Quill Gardens Boutique Hotel

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
  • Use the map to find apartments and other holiday homes in the Windward Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windward Side while they last

Look no further and take a look at our great range of rental properties in Windward Side!

Frequently asked questions

Are there holiday rentals in Windward Side?

Yes, there are holiday rentals close to the most popular sights in Windward Side, or you can select 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 holiday rentals that Windward Side has to offer?

Beautiful Traditional Saba Cottage With all the Modern Amenities: This highly rated holiday home rental in Windward Side is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities such as a stovetop and a microwave can make your holiday 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 holiday rentals are there in Windward Side?

With 3 Expedia holiday rentals, you're guaranteed 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 holiday rental in Windward Side like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windward Side. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.