Photo by Meghan Watters

Search Holiday Rentals in Windward Side

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Top Holiday Rentals in Windward Side

Beautiful Gingerbread Cottage - Spectacular View & Pool
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
Spyglass is a Private Villa With 360 View Near Windwardside.
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!
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!
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Beautiful Traditional Saba Cottage With all the Modern Amenities
Property grounds
Beautiful Traditional Saba Cottage With all the Modern Amenities
Beautiful Traditional Saba Cottage With all the Modern Amenities
Home a way from home in the Unspoiled queen of the Caribbean.
Exterior
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.
2023 Villa Fairview on Saba. Ultimate privacy.
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.
Poets and Painters Cottage
Property grounds
Poets and Painters Cottage
The price is £335
includes taxes & fees
7 May - 8 May
Poets and Painters Cottage
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
Pool | Outdoor 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.
Palm Spring Inn
Suite, 2 Bedrooms | Private kitchenette | Full-sized fridge, microwave, coffee/tea maker
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
Studio apartment in quiet neighborhood.
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.

Windward Side Holiday Rental Travel Info

Number of holiday rentals
2
Popular accommodation
Windward Side villas
Known landmarks
Well's Bay Beach, Cove Bay Beach and Dutch Museum of Saba
International airport
Saba (SAB-Juancho E. Yrausquin)

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

Saba Arawak Hotel
View from room
Saba Arawak Hotel
3.0 star property
8.6 out of 10, Excellent, (28)
"I selected this property because of how close it is to hiking trails. This is perfect if that’s why you’re visiting the island. It is also close to a supermarket and plenty of restaurants. I didn’t have any issues with wifi at all which seems to be complaints from previous guests. Overall I had a nice stay and the staff and owner were very nice and helpful! "
The price is £121
includes taxes & fees
5 May - 6 May
Saba Arawak Hotel
El Momo Cottages
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. "
The price is £85
includes taxes & fees
11 May - 12 May
El Momo Cottages
Beautiful Gingerbread Cottage - Spectacular View & Pool
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 £334 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. 

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.

How many holiday rentals are there in Windward Side?

With 4 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 Harry L Johnson Museum, whereas Mt Scenery is one spot to enjoy nature. Other places in town to visit include Saba Heritage Center 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.

Recent reviews of Windward Side properties
Expedia verified reviews

The Old Gin House Hotel

The Old Gin House Hotel

5/5 Excellent
"The new owners are working hard to refresh this historic property. The seaside location is a gem and the staff members are friendly and attentive (special shout-out to Julia). The full breakfast is a wonderful benefit, and my mahi-mahi dinner was absolutely delicious! An added bonus is the proximity to another excellent restaurant, as well as a scuba center for those who come to Statia to dive. Thanks to Peter and Jeanette and your amazing staff!"
A verified traveller stayed at The Old Gin House Hotel
Posted 2 weeks ago
The Old Gin House Hotel