Photo by Meghan Watters

Windward Side Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Sept - 8 Sept
Tomorrow
8 Sept - 9 Sept
Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept

Holiday Rentals in Windward Side

Flamboyant Cottage - Spectacular View & Pool
Property grounds

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (40)
"Great experience. Trisha and Michael were more than welcoming and helpful. Incredible location and views. "
Flamboyant Cottage - Spectacular View & Pool
Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (69)
"This property is absolutely stunning! Views are amazing and just a really great place to stay. "
Spyglass is a Private Villa With 360 View Near Windwardside.
Peter Hytte is close to everything at great price!
Property grounds

Peter Hytte is close to everything at great price!

10.0 out of 10, Exceptional, (2)
"Cozy well equipt cottage. From hiking sticks to water filter and from coffee to insect repellent (not used). Etcetera.You name it."
Peter Hytte is close to everything at great price!
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Property grounds

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

10.0 out of 10, Exceptional, (11)
"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Home a way from home in the Unspoiled queen of the Caribbean.
Terrace/patio

Home a way from home in the Unspoiled queen of the Caribbean.

10.0 out of 10, Exceptional, (3)
"Iris House is cute, comfortable, great/walkable location and with everything we needed for a great stay. Owner and manager both very helpful - highly recommend."
Home a way from home in the Unspoiled queen of the Caribbean.
Palm Spring Inn
Front of property

Palm Spring Inn

3.0 star property
8.6 out of 10, Excellent, (14)
"Great place lovely staff"
The price is HK$897
HK$995 total
includes taxes & fees
18 Sept - 19 Sept
Palm Spring Inn
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
Outdoor pool

Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.

10.0 out of 10, Exceptional, (4)
"Literally on the edge of runway to view planes taking off and excellent view of mountains/ocean."
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Fridge, microwave, oven, stovetop

Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad

The price is HK$1,053
HK$1,251 total
includes taxes & fees
13 Sept - 14 Sept
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
La Vie est Belle
Living area

La Vie est Belle

La Vie est Belle
Cozy 2-bedroom apartment with AC, WiFi in fabulous Oranjestad
Terrace/patio

Cozy 2-bedroom apartment with AC, WiFi in fabulous Oranjestad

Cozy 2-bedroom apartment with AC, WiFi in fabulous Oranjestad
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Fridge, microwave, oven, stovetop

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

The price is HK$1,053
HK$1,251 total
includes taxes & fees
13 Sept - 14 Sept
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Studio apartment in quiet neighborhood.
Exterior

Studio apartment in quiet neighborhood.

Studio apartment in quiet neighborhood.
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.
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

Find out more about Windward Side

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.