Photo by Meghan Watters

Windward Side Holiday Rentals

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Holiday Rentals in Windward Side

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.
Flamboyant Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (36)
"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, (64)
"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...
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, (8)
"Three of us came to Saba for the first time, for a diving vacation. We had a great time and Althea's Cottage worked out perfectly for us. The 2 bedrooms with bath were at opposite ends of the house, we had a kitchen with dining, a large living room sitting area and back yard patio area. We were able to use an outdoor clothesline daily for drying our diving attire. The cottage is located with convenient walking access several restaurants, 2 grocery stores, a delicious bakery. and the Swinging...
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, (1)
"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."
Beautiful Traditional Saba Cottage With all the Modern Amenities
Peter Hytte is close to everything at great price!
Peter Hytte is close to everything at great price!
Your very own cottage
Your very own cottage
Poets and Painters Cottage
The price is NZ$686
includes taxes & fees
6 Nov - 7 Nov
Poets and Painters Cottage
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.
Forever Young Apartment B
The price is NZ$268
includes taxes & fees
8 Nov - 9 Nov
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
The price is NZ$234
includes taxes & fees
7 Nov - 8 Nov
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
8.4 out of 10, Very good, (31)
"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 NZ$254
includes taxes & fees
6 Nov - 7 Nov
Saba Arawak Hotel
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$177
includes taxes & fees
8 Nov - 9 Nov
El Momo Cottages
Flamboyant Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (36)
"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
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?

Poets and Painters Cottage: This highly rated holiday home rental in Windward Side offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of books in this rental home to help you unwind.

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 Jo Bean Glass Art Studio and Harry L Johnson Museum.

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.