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Windward Side Holiday Rentals

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Holiday Rentals in Windward Side

Property grounds
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (6)
"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
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.
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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.
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)
"Very nice villa with some of the most spectacular views you’ll find anywhere in the world. Good hikers can walk into/from the village of Windwardside — be prepared for a steep hill on return. We were 4 adults, though 6 would be very comfortable. All conveniences are in the house. Mgmt: 1 sink awaiting repair parts; we never found the orientation book. We appreciated the mid-week cleaning service, but would like to be notified of that before they intrude on our privacy."
Spyglass is a Private Villa With 360 View Near Windwardside.
Suite, 2 Bedrooms | Private kitchenette
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
Property grounds
Beautiful Traditional Saba Cottage With all the Modern Amenities
Beautiful Traditional Saba Cottage With all the Modern Amenities
Terrace/patio
Your very own cottage
Your very own cottage
Property grounds
Poets and Painters Cottage
The price is NZ$672
per night
18 May - 19 May
Poets and Painters Cottage
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.

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

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)
"Very nice villa with some of the most spectacular views you’ll find anywhere in the world. Good hikers can walk into/from the village of Windwardside — be prepared for a steep hill on return. We were 4 adults, though 6 would be very comfortable. All conveniences are in the house. Mgmt: 1 sink awaiting repair parts; we never found the orientation book. We appreciated the mid-week cleaning service, but would like to be notified of that before they intrude on our privacy."
Spyglass is a Private Villa With 360 View Near Windwardside.
View from room
Saba Arawak Hotel
3.0 star property
8.6 out of 10, Excellent, (29)
"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$251
per night
22 May - 23 May
Saba Arawak Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windward Side holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windward Side. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windward Side. Seeing all the best attractions is bound to make you fall in love with Windward Side. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windward Side short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Windward Side?

With 4 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 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 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.

Recent reviews of Windward Side properties
Expedia verified reviews

Saba Arawak Hotel

Saba Arawak Hotel

5/5 Excellent
"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. "
A verified traveller stayed at Saba Arawak Hotel
Posted 11 days ago
Saba Arawak Hotel