Windward Side Vacation Rentals from ￥19,722: Search Short-Term Rentals

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Vacation Rentals in Windward Side

"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."

"Great experience. Trisha and Michael were more than welcoming and helpful. Incredible location and views. "

"Cozy well equipt cottage. From hiking sticks to water filter and from coffee to insect repellent (not used). Etcetera.You name it."

"This property is absolutely stunning! Views are amazing and just a really great place to stay. "

"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."

"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."

Suite, 2 Bedrooms | Private kitchenette | Full-size fridge, microwave, coffee/tea maker

"Great place lovely staff"

￥18,648 total

includes taxes & fees

Jun 23 - Jun 24

"Literally on the edge of runway to view planes taking off and excellent view of mountains/ocean."

￥20,453 total

includes taxes & fees

Jun 23 - Jun 24

￥23,433 total

includes taxes & fees

Jun 28 - Jun 29

￥23,433 total

includes taxes & fees

Jun 28 - Jun 29

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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:

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Look no further and take a look at our great range of rental properties in Windward Side!

Recent reviews of Windward Side properties

5/5 Excellent

"Property managers are awesome "

A verified traveler from Pembroke Pines stayed at Quill Gardens Boutique Hotel

Posted 1 month ago

5/5 Excellent

"Loved my stay at El Momo! It's rustic and a climb up the 60 steps, but the views are amazing, Andries was helpful and welcoming, and it's SO peaceful. Definitely not a chain hotel, but if you're looking for a quiet, quaint cottage and don't mind a frog or gecko passing through - it's wonderful! The Sunshine cottage has a shower overlooking the ocean and was perfect!"

A verified traveler stayed at El Momo Cottages

Posted 2 months ago

5/5 Excellent

Spectacular

"So lovely , whimsical, the view, the pool was so wonderful to cool off. Saba is magical.The cottage was clean and so many outdoor sitting spots.Could not recommend it more "

A verified traveler from Ontario, Canada stayed at Flamboyant Cottage - Spectacular View & Pool

Posted 4 months ago

Spyglass is a Private Villa With 360 View Near Windwardside.

5/5 Excellent

World Class experience

"The villa is even more beautiful than the pictures. The views and gardens are even more vibrant and incredible than we expected. We were amazed at the incredible construction and attention to detail in the house. The building itself looks like much of the wood work and interior is custom built and individually crafted. All appliances and appointments are top notch. The atmosphere is so peaceful. Overall the villa is airy, spacious, bright and with views into the infinity of the Caribbean. "

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

Posted 4 months ago

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

5/5 Excellent

Saba relaxation

"Excellent place to stay for a family with kids. The pool was perfect for the kids to use up some energy. And cool off after a hike or walking the hills. The beautiful breeze that enters the main bedroom is amazing and little need for the ac to be on. Will definitely recommend to others."

A verified traveler stayed at Home a way from home in the Unspoiled queen of the Caribbean.

Posted 4 months ago

Beautiful Traditional Saba Cottage With all the Modern Amenities

5/5 Excellent

A beautiful cottage on The Windward Side.

"We really enjoyed our stay in this beautiful cottage. It's location is great on the Windward Side of Saba. Close to My Scenery, several shops, basically everything you need. The home was spotless and had all the amenities you could ask for. Communication was great and check in was seamless. Margarita was great. I highly recommend it. Looking forward to returning to Saba soon."

A verified traveler stayed at Beautiful Traditional Saba Cottage With all the Modern Amenities

Posted 7 months ago

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

Posted 8 months ago

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?

Beautiful Traditional Saba Cottage With all the Modern Amenities: This Windward Side vacation home rental is located in the mountains and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a stovetop and a microwave can make your vacation 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 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.

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Windward Side Vacation Rentals

Check prices for these dates

Vacation Rentals in Windward Side

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

Flamboyant Cottage - Spectacular View & Pool

Peter Hytte is close to everything at great price!

Spyglass is a Private Villa With 360 View Near Windwardside.

Your very own cottage

Beautiful Traditional Saba Cottage With all the Modern Amenities

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

Palm Spring Inn

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

Forever Young Apartment B

Forever Young Apartment A

Studio apartment in quiet neighborhood.

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

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

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

Find out more about Windward Side

Recent reviews of Windward Side properties

Quill Gardens Boutique Hotel

Saba Arawak Hotel

El Momo Cottages

Flamboyant Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

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

The Old Gin House

Beautiful Traditional Saba Cottage With all the Modern Amenities

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

Frequently asked questions