Windward Side Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

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)
"Great place lovely staff"
United States
Dameon
The price is ￥18,295
￥20,307 total
includes taxes & fees
Apr 26 - Apr 27
Palm Spring Inn
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 ￥21,477
￥25,518 total
includes taxes & fees
Apr 19 - Apr 20
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 ￥21,477
￥25,518 total
includes taxes & fees
Apr 19 - Apr 20
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
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 ￥21,396
￥31,266 total
includes taxes & fees
Apr 18 - Apr 19
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windward Side Hotel Reviews

Talk of the Town Inn & Suites

Talk of the Town Inn & Suites

8/10 Good
"This is a nice place to stay when visiting Statia. They have good electric bikes (not for free), which is the best way to get around the island and know every corner of it."
José Miguel 2-night trip
Posted 5 days ago
Talk of the Town Inn & Suites

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 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.

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 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 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.