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Windward Side Vacation Rentals

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Vacation Rentals in Windward Side

Beautiful Gingerbread Cottage - Spectacular View & Pool
Exterior
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.
9.8 out of 10, Exceptional, (63)
"This is amazing place. I was so happy for having a chance to book the spyglass. If you plan to go visit Saba, this is the place to stay!!!"
Spyglass is a Private Villa With 360 View Near Windwardside.
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Property grounds
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (7)
"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!
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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.
Your very own cottage
Terrace/patio
Your very own cottage
Your very own cottage
Poets and Painters Cottage
Property grounds
Poets and Painters Cottage
The price is ￥56,448
￥64,288 total
includes taxes & fees
Jun 2 - Jun 3
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-size 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.
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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.

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
8.4 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 ￥20,227
￥23,786 total
includes taxes & fees
Jun 7 - Jun 8
Saba Arawak Hotel
El Momo Cottages
Outdoor pool, sun 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. "
El Momo Cottages
Beautiful Gingerbread Cottage - Spectacular View & Pool
Exterior
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.

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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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 equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly. Other favorite homes for rent in Windward Side are Home a way from home in the Unspoiled queen of the Caribbean. and Poets and Painters Cottage.

How many vacation rentals are there in Windward Side?

With 4 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 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 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.

Recent reviews of Windward Side properties
Expedia verified reviews

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!

5/5 Excellent
Diving vacation in Saba.
"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 Door Bar. We went on 2 hikes which were also within walking distance. The weather was favorable to keeping the doors and winds open which allowed the tropical breeze to flow through the rooms. Jeff our host, was very accommodating and help us with any needs or questions. We all agree it would be nice to return."
A verified traveler stayed at Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Posted 2 weeks ago
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!