Vacation rentals in Windward Side

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Top-rated vacation rentals in Windward Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Windwardside

4.9 out of 5 average rating, 40 reviews

Beautiful traditional Saba Cottage

This charming 2 bedroom Saba cottage was built in 2007 yet anyone walking by would think the home is one of the original Saba homes. The exterior of the home follows the traditional Saba gingerbread style while the interior is modern and spacious. Located directly in the quaint village of Windward side yet adjacent to the museum and it's beautiful gardens. It's just a short stroll to Windward side's restaurants, bars, stores as well as the start of the hiking trail to Mount Scenery.

Guest favorite

Vacation home in Windwardside

4.91 out of 5 average rating, 47 reviews

Peter Hytte by Althea

This property in Windwardside features stunning views of the blue Caribbean, the misty top of spectacular Mt. Scenery, and the picturesque village below. On my 30th trip to Saba in 2019 I bought the 1858 vintage Althea Cottage. In 2021 I completed a second stone house for myself at the rear. In 2022 a second stone apartment, Peter Hytte, was built between the two other cottages... smaller, priceworthy and efficient. All net income is donated to my charities. I charge no cleaning fee.

Home in Windward Side

4.86 out of 5 average rating, 7 reviews

Cloudbreak Villa

Tucked amongst tropical gardens & walking distance to the center of town, Cloudbreak Villa offers guests the ultimate experience of tranquility paired with new, modern amenities. Completed in fall of 2017 the luxurious home boasts 3 large bedrooms (perfect for up to 7 guests), 2 full ensuite bathrooms, ocean & island views from every room & a stunning, stocked, gourmet kitchen. Modern upgrades including pool, A/C, gas stove, indoor/outdoor living spaces, wifi, gardens, laundry, & TV.

Apartment in Oranjestad

4.8 out of 5 average rating, 5 reviews

George's Petite Studio Apartment - St. Eustatius

Visiting the island of St. Eustatius for work or pleasure and you are searching for temporary housing while on island? If yes, then George’s studio apartment is the right place for your short term stay. The space is petite/small, but fully equipped located on the tranquil island of St. Eustatius. Description of space: Open concept studio fully equipped with all kitchen amenities, towels, sheets, clothes iron, water heater, etc. Lots of parking available on the property

Villa in The Bottom

5 out of 5 average rating, 3 reviews

Magnificent private hilltop villa on magical Saba

Dear guest, a warm welcome at the Haiku House, a lovely place to stay on one of the most exclusive and sustainable islands of the Caribbean, Saba. We invite you to enjoy our luxurious villa, the beautiful pool with ocean view surrounded by nature and landscape of this hidden gem of the Caribbean. Chances are you will fall in love with this island, like we did about 25 years ago.

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Villa in Booby Hill

4.98 out of 5 average rating, 41 reviews

Spyglass Villa Charms!

Spyglass is a private villa located in Booby Hill within walking distance of Windwardside. Spyglass Villa is a haven of tranquility and beauty and features a walkout panoramic veranda with extraordinary views of nearby islands, sea and mountains.