Vacation rentals in Windward Side

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Top-rated vacation rentals in Windward Side

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Apartment in Oranjestad

4.64 out of 5 average rating, 39 reviews

A Quiet Getaway.

My place is very close to a tiny secluded rocky beach. You will love it for the view of the Atlantic ocean, the seclusion, the sound of the waves, the privacy.. It is great for couples and solo adventurers. Town, shops etc is a brisk 20-30 minutes walk. I cannot emphasize enough that the area is secluded. Transportation is advised because of the distance but the island is small. We also rent SUVs for an discount price for tenants. Please note: This place is located on St Eustatius, NOT on Saba.

Sep. 27 – Oct. 4

$107 CAD per night

Home in Oranjestad

4.67 out of 5 average rating, 6 reviews

Townhouse in the historical heart

Experience authentic St. Eustatius by staying at this Airbnb. Key historical grounds (such as fort Oranje) are just minutes away by foot. Take nice evening strolls to the harbor and bayside where you can find restaurants and bars. Choosing to stay in? There is a mini market right across the street where you can find all kinds of provisions. Please note that the property is in the bustling city center which means it can be noisy. There are bars very nearby which can have music in the weekends.

Oct. 24 – 31

$97 CAD per night

Guest favourite

Home in Windwardside

4.88 out of 5 average rating, 34 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.

Apr. 22 – 29

$384 CAD per night

Guest favourite

Vacation home in Windwardside

4.96 out of 5 average rating, 28 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.

Aug. 9 – 16

$226 CAD per night

Home in Windward Side

5.0 out of 5 average rating, 5 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.

Mar. 6 – 13

$655 CAD per night

Apartment in Oranjestad

4.75 out of 5 average rating, 4 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

Jun. 24 – Jul. 1

$100 CAD per night

Apartment in Zion's Hill

4.94 out of 5 average rating, 16 reviews

Private studio Behind the Ridge

The apartment is downstairs from our house above. We are at the end of the road so it is usually quiet. At night the only sounds are nature and when cars come to turn at the end of the road. There are 180 degree views of the ocean. It's a great place to watch birds catching the updrafts. You will need a car to get around Saba from here or use the various taxis. There is access to some great hiking trails right from our driveway.

Jun. 20 – 27

$132 CAD per night

Apartment in Oranjestad

4.5 out of 5 average rating, 26 reviews

Private and cozy studio apartment

Studio apartment in a quiet neighborhood. Offers enough space for two people. Air conditioned, with hot water shower and WIFI. Refrigerator, microwave and hot water pot for tea or coffee. If you enjoy walking, the studio apartment is a 30 minute walk to the Quill. From the airport 20 min walk or 7 min by taxi. Restaurants and grocery shopping is also in walking distance. We look forward to hosting your next getaway.

Nov. 29 – Dec. 6

$157 CAD per night

Apartment in Oranjestad

5.0 out of 5 average rating, 3 reviews

Perfect 1 bedroom apartment

Stylish newly decorated apartment with pool access. Centrally located walking distance from the airport, bakery, supermarket. Small complex with pool and housekeeping services. Washer & dryer on premises. It’s a lovely place in a central spot on St. Eustatius. Full kitchen, airconditioning and we’ll appointed with class furniture. Stay in style & comfort without breaking the bank.

Aug. 29 – Sep. 5

$257 CAD per night

Villa in The Bottom

5.0 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.

Dec. 13 – 20

$1,072 CAD per night

Superhost

Cottage in Windwardside

4.68 out of 5 average rating, 25 reviews

House on The Path

Welcome to "House on The Path". Nestled 1500 feet above sea level, "House on The Path" is a charming restored, original Saban style cottage with an intimate setting. It is secluded by a five minute hike isolated from neighbors and traffic. The house is a perfect romantic vacation cottage for honeymoon couples and an exciting adventure for those interested in an Eco Experience.

Apr. 24 – May 1

$248 CAD per night

Superhost

Villa in Booby Hill

4.97 out of 5 average rating, 35 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.

Oct. 29 – Nov. 5

$707 CAD per night