Photo by Meghan Watters

Windward Side Holiday Rentals

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Holiday Rentals in Windward Side

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (37)
"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. "
Flamboyant Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (66)
"We loved it here so much, we already booked it for Christmas next year. nuff said. "
Spyglass is a Private Villa With 360 View Near Windwardside.

Peter Hytte is close to everything at great price!

Peter Hytte is close to everything at great price!

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

10.0 out of 10, Exceptional, (10)
"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."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Beautiful Traditional Saba Cottage With all the Modern Amenities

10.0 out of 10, Exceptional, (2)
"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."
Beautiful Traditional Saba Cottage With all the Modern Amenities

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.

Your very own cottage

Your very own cottage

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

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

Forever Young Apartment B

The price is NZ$283
includes taxes & fees
23 Jan - 24 Jan
Forever Young Apartment B

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

Forever Young Apartment A

Forever Young Apartment A

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

Saba Arawak Hotel

3.0 star property
8.6 out of 10, Excellent, (41)
"Staff is friendly and helpful. They allowed me to stay for a couple of hours more to enjoy a snorkeling tour and come back for quick shower. Rooms are big and quiet. They have a restaurant on site in case you don't want to go out."
The price is NZ$267
includes taxes & fees
31 Jan - 1 Feb
Saba Arawak Hotel

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (37)
"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. "
Flamboyant Cottage - Spectacular View & Pool

El Momo Cottages

3.0 star property
8.6 out of 10, Excellent, (47)
"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. "
The price is NZ$252
includes taxes & fees
17 Feb - 18 Feb
El Momo Cottages
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.

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 offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable 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.