A calm sea with a mountain in the distance.

Windward Side Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windward Side holiday rentals

Front of property

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 HK$1,128
HK$1,252 total
includes taxes & fees
2 Sept - 3 Sept
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
"Great stay. Everything was superb."
Donald 4-night trip
Posted 1 month 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 Saba Heritage Center and Dutch Museum of Saba, 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.