Photo by Meghan Watters

Holiday Rentals in Windward Side

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Windward Side

Exterior
Beautiful Gingerbread Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (32)
"This place was beautiful, so peaceful and the views and pool were perfect. A well appointed kitchen and plenty of outdoor spaces to enjoy. Michael was an extremely helpful host coordinating transport easily and even making the occasional dinner reservation for us. Wonderful island, visit if you feel like completely relaxing!"
Beautiful Gingerbread Cottage - Spectacular View & Pool
Outdoor dining
Spyglass is a Private Villa With 360 View Near Windwardside.
10.0 out of 10, Exceptional, (61)
"Very nice villa with some of the most spectacular views you’ll find anywhere in the world. Good hikers can walk into/from the village of Windwardside — be prepared for a steep hill on return. We were 4 adults, though 6 would be very comfortable. All conveniences are in the house. Mgmt: 1 sink awaiting repair parts; we never found the orientation book. We appreciated the mid-week cleaning service, but would like to be notified of that before they intrude on our privacy."
Spyglass is a Private Villa With 360 View Near Windwardside.
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (6)
"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!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Beautiful Traditional Saba Cottage With all the Modern Amenities
Beautiful Traditional Saba Cottage With all the Modern Amenities
Terrace/patio
Home a way from home in the Unspoiled queen of the Caribbean.
10.0 out of 10, Exceptional, (2)
"Even though we had to pay for an unused night on account of a canceled ferry, this was a beautiful place in a gorgeous location close to everything in Windwardside. My kids and I enjoyed the private pool with a view."
Home a way from home in the Unspoiled queen of the Caribbean.
Pool
2023 Villa Fairview on Saba. Ultimate privacy.
10.0 out of 10, Exceptional, (3)
"Villa Fairview was gorgeous! The views and the ambiance are unbeatable, and visitors get the full island experience: amazing sunsets, hills, cloud cover, rain, and ocean breezes. Leaving the doors open is magical, but it does come with a side of insects that serve to contribute to the experience. The pool will cool you off on a hot day, and the place has everything you could need, including a great kitchen and laundry room. I’d definitely stay here again!"
2023 Villa Fairview on Saba. Ultimate privacy.
Terrace/patio
Your very own cottage
Your very own cottage
Poets and Painters Cottage
The price is €389
per night
18 May - 19 May
Poets and Painters Cottage
Pool
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
10.0 out of 10, Exceptional, (4)
"Our stay was fantastic! Cece was awesome and helpful in every way! She arranged a rental car for us at the house so we could get around the island independently. Views were magnificent and hacienda was perfect! Very clean with every amenity you could possibly want! Kitchen is fully stocked with anything you could possibly need to cook a meal. Don’t hesitate to book this magnificent home! You won’t be sorry!"
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
Suite, 2 Bedrooms | Private kitchenette
Palm Spring Inn
3.0 star property
8.6 out of 10, Excellent, (14)
"Arrived late, well advanced noticed sent to owner. Was met by a man at hotel who showed us suite and gave us keys and wifii password. This man told us the owner will comeby the following day. No show. Apartment was nasty as if the last guest left and we arrived. Used bag of ice in freezer, dish on dish rack, used toiletries. No microwave and no feee bottled water. Shower stank after use because water stayed stagnant for good hour to two or so after use. I emailed owner about microwave,...
Palm Spring Inn
Exterior
Studio apartment in quiet neighborhood.
Studio apartment in quiet neighborhood.
Don't see what you're looking for?
See all available properties in Windward Side
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.

Other types of properties in Windward Side you may be interested in

View from room
Saba Arawak Hotel
3.0 star property
8.6 out of 10, Excellent, (29)
"Very good manager. He took care of us like a good friend. When we couldn't find a taxi late in the night he even dropped by niece at the dome. Highly appreciated. "
The price is €141
per night
11 May - 12 May
Saba Arawak Hotel
Outdoor pool, pool loungers
El Momo Cottages
3.0 star property
8.6 out of 10, Excellent, (44)
"We had a great weekend in Saba. The owners were very nice and welcoming and the cottages were comfortable. Near lovely restaurants and shops, and close to the trails. Breakfast was great and pool refreshing. Only downside was the noise at night from neighborhood dogs barking and early roosters. We did not sleep well. "
El Momo Cottages
Exterior
Beautiful Gingerbread Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (32)
"This place was beautiful, so peaceful and the views and pool were perfect. A well appointed kitchen and plenty of outdoor spaces to enjoy. Michael was an extremely helpful host coordinating transport easily and even making the occasional dinner reservation for us. Wonderful island, visit if you feel like completely relaxing!"
Beautiful Gingerbread Cottage - Spectacular View & Pool
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.

Everything you need to know about Windward Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windward Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windward Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windward Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windward Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windward Side holiday rentals we have selected for you start as low as €389 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windward Side rentals

At Expedia, we put the best Windward Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windward Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windward Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windward Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews of Windward Side properties
Expedia verified reviews

Saba Arawak Hotel

Saba Arawak Hotel

5/5 Excellent
"Very good manager. He took care of us like a good friend. When we couldn't find a taxi late in the night he even dropped by niece at the dome. Highly appreciated. "
A verified traveller stayed at Saba Arawak Hotel
Posted 5 days ago
Saba Arawak Hotel