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Windward Side Vacation Rentals

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Vacation Rentals in Windward Side

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
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.
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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Property grounds
Beautiful Traditional Saba Cottage With all the Modern Amenities
Beautiful Traditional Saba Cottage With all the Modern Amenities
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.
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.
Terrace/patio
Your very own cottage
Your very own cottage
Property grounds
Poets and Painters Cottage
The price is $360
$410 total
includes taxes & fees
May 22 - May 23
Poets and Painters Cottage
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.
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
Exterior
Studio apartment in quiet neighborhood.
Studio apartment in quiet neighborhood.
Don't see what you're looking for?
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.

Windward Side Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Windward Side villas
Known landmarks
Well's Bay Beach, Cove Bay Beach and Dutch Museum of Saba
International airport
Saba (SAB-Juancho E. Yrausquin)

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

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 $129
$152 total
includes taxes & fees
May 22 - May 23
Saba Arawak Hotel
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
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.

Everything you need to know about Windward Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windward Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windward Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $360 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windward Side rentals

At Expedia, we put the best Windward Side vacation 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 vacation.

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.

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