Windward Side Holiday Rentals from €138: Search Short-Term Rentals

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Holiday Rentals in Windward Side

"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."

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local...

"The people of Saba are very friendly. This location has many fantastic restaurant choices within a short walk. Our host Jeffery was wonderful. Very helpful. Because he lives next door he's always available. The cottage was roomy for the 2 of us. WiFi worked great and there's plenty of electrical outlets (American Style 110 volt). I can say enough nice things about this rental."

includes taxes & fees

30 Nov - 1 Dec

"The cottage is great, just as described. The beds are comfortable and clean. All of Windwardside is walking distance from this location, the grocery store is steps away. I would definitely stay here again."

"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!"

includes taxes & fees

29 Nov - 30 Nov

"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,...

includes taxes & fees

29 Nov - 30 Nov

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

"Beautiful pool and nice view from balcony. Bed was okay. Breakfast at Liam's was good. Short walk into town. Good price for what you get. Nice to have kitchen if you want to cook."

includes taxes & fees

8 Dec - 9 Dec

"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "

includes taxes & fees

2 Dec - 3 Dec

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

Find out more about Windward Side

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 €138 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

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

5/5 Excellent

Great Little Community

"The people of Saba are very friendly. This location has many fantastic restaurant choices within a short walk. Our host Jeffery was wonderful. Very helpful. Because he lives next door he's always available. The cottage was roomy for the 2 of us. WiFi worked great and there's plenty of electrical outlets (American Style 110 volt). I can say enough nice things about this rental."

A verified traveller from McConnellsville, NY USA stayed at Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Posted 8 hours ago

5/5 Excellent

Fun and Eco Friendly

"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "

A verified traveller stayed at El Momo Cottages

Posted 2 months ago

Beautiful Traditional Saba Cottage With all the Modern Amenities

5/5 Excellent

Just as described

"The cottage is great, just as described. The beds are comfortable and clean. All of Windwardside is walking distance from this location, the grocery store is steps away. I would definitely stay here again."

A verified traveller from Cleveland stayed at Beautiful Traditional Saba Cottage With all the Modern Amenities

Posted 3 months ago

Beautiful Gingerbread Cottage - Spectacular View & Pool

5/5 Excellent

Unspoiled Queen of the Caribbean

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

A verified traveller stayed at Beautiful Gingerbread Cottage - Spectacular View & Pool

Posted 3 months ago

Spyglass is a Private Villa With 360 View Near Windwardside.

5/5 Excellent

Wonderful home. Amazing location.

"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local shops and restaurants are. We enjoyed the spectacular views of each sunrise and sunset with a good book in hand. We'll be back soon!"

A verified traveller stayed at Spyglass is a Private Villa With 360 View Near Windwardside.

Posted 6 months ago

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

Posted 8 months ago

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?

Home a way from home in the Unspoiled queen of the Caribbean.: This highly rated holiday home rental in Windward Side is located in the city centre, and has an outdoor pool, a patio and a BBQ 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 holiday with amenities such as a garden. Other favourite homes for rent in Windward Side are Poets and Painters Cottage and Beautiful Traditional Saba Cottage With all the Modern Amenities.

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 Saba Heritage Center, 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.

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Holiday Rentals in Windward Side

Check Windward Side holiday rental availability

Holiday Rentals in Windward Side

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

Flamboyant Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

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

Poets and Painters Cottage

Beautiful Traditional Saba Cottage With all the Modern Amenities

Peter Hytte is close to everything at great price!

Your very own cottage

Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.

Forever Young Apartment B

Palm Spring Inn

Forever Young Apartment A

Studio apartment in quiet neighborhood.

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

Saba Arawak Hotel

El Momo Cottages

Flamboyant Cottage - Spectacular View & Pool

Find out more about Windward Side

Recent reviews of Windward Side properties

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

El Momo Cottages

Quill Gardens Boutique Hotel

Beautiful Traditional Saba Cottage With all the Modern Amenities

Beautiful Gingerbread Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

Saba Arawak Hotel

The Old Gin House

Talk of the Town

Frequently asked questions