Vacation rentals in Windward Side

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windward Side

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Windwardside, Bonaire, Sint Eustatius and Saba

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.

Jun 30 – Jul 7

R5,232 ZAR per night

Guest favorite

Vacation home in Windwardside, Bonaire, Sint Eustatius and Saba

4.93 out of 5 average rating, 29 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.

Jan 8 – 15

R3,148 ZAR per night

Guest favorite

Home in Saint-Barthélemy, St. Barthélemy

4.97 out of 5 average rating, 119 reviews

North Star

ETOILE DU NORD is located facing Flamand beach, from which you can enjoy the exceptional view from every corner of the villa modern, functional, it is ideal for a couple or family with large children who will appreciate the independence of the second bedroom located on the lower level. All you have to do is cross the road to get to the beach, whether it's for a morning swim in the rising sun, a lazy day, or an evening stroll along the bay .

Sep 20 – 27

R5,001 ZAR per night

Guest favorite

Apartment in BL, St. Barthélemy

4.99 out of 5 average rating, 69 reviews

Gemma apartment

New and modern apartment, located just a short walk to the beautiful Flemish beach and the small cove. The accommodation is a 5-minute walk from the trail that leads to the beach of Grand Colombier, one of the most beautiful beaches in Saint-Barthélemy. It will take you a short drive to reach Gustavia's shops and restaurants. Fully air-conditioned and equipped apartment can only be suitable for you to discover and enjoy Saint-Barthélemy

Feb 22 – Mar 1

R5,388 ZAR per night

Guest favorite

Villa in Saint Barthélemy, St. Barthélemy

4.98 out of 5 average rating, 127 reviews

Villa RIDE

RIDE is a 2017 VILLA located on hilltop of anse des cayes offering a beautiful seaview. 5 min driving from the beach , gustavia ( main city ) , and a delicious bakery store. It offers quiet and privacy while remaining close to everything. The villa can welcome 4 PEOPLE in 2 BEDROOMS, each one having their own private massive wood bathroom . The villa is also accessible to people with REDUCED MOBILITY thanks to its one level access.

Nov 12 – 19

R14,111 ZAR per night

Guest favorite

Apartment in BL, St. Barthélemy

5.0 out of 5 average rating, 17 reviews

Luxury apartment 2 steps from the St Jean beach

Beautiful spacious and bright 1 bedroom apartment, ideally located 100 m from St Jean beach, 4 minutes drive from the airport and 8 minutes from Gustavia (La Capitale). You can shop in the many shops of the lively St Jean district and will be a 2-minute walk to the famous beach restaurants: Eden Rock, Nikki Beach, Gypsea and La Guérite. I would love to host you to make your stay an unforgettable one!

Aug 24 – 31

R7,460 ZAR per night

Guest favorite

Condo in Saint-Bathélémy, St. Barthélemy

5.0 out of 5 average rating, 57 reviews

Cadence- Studio

Welcome to Residence Cadence. Located in the heart of the island, in the Camaruche district, this new 45 m2 apartment located in a new residence on the ground floor offers many assets. It has a terrace, a double bedroom, a large bathroom with double sink and walk-in shower as well as a fully equipped kitchen and living area. Its modern and tropical decor will take you on a journey!

Jul 26 – Aug 2

R3,191 ZAR per night

Superhost

Villa in Anse Des Cayes, St. Barthélemy

4.95 out of 5 average rating, 116 reviews

The Perfect Beach House

Villa Palmier is a stunning 2 bedroom, 2 bathroom newly renovated villa in the well located neighborhood of Anse Des Cayes. It is a designers dream having just been featured in the July/August issue of Elle Decor France. With ocean views from every room, a constant sea breeze blowing throughout, and your own private pool, it's the perfect beach retreat.

Oct 19 – 26

R17,346 ZAR per night

Guest favorite

Apartment in BL, St. Barthélemy

5.0 out of 5 average rating, 29 reviews

Amazing view 2 min walk to the beach!

Beautiful one bedroom apartment tastefully renovated, in the heart of St Jean, 2 minutes walk from the beach, restaurants and shops. The accommodation is fully equipped, large kitchen, 2 smart TVs, internet, sonos, etc... Let yourself be seduced by the cozy and soothing atmosphere with views of the sea, the beach and the neighboring islands.

Apr 11 – 18

R10,232 ZAR per night

Guest favorite

Guest suite in BL, St. Barthélemy

4.96 out of 5 average rating, 54 reviews

Independent entrance studio and kitchen in Flamands

Welcome to this air-conditioned, peaceful and comfortable studio located at about 150 meters from the beautiful beach of Flamands accessible by foot. The studio is composed of a functional kitchen, an elegant and large bathroom as well as an independent terrace overlooking a tropical garden. No vis-a-vis.

Jun 12 – 19

R3,178 ZAR per night

Guest favorite

Home in Lorient, Saint Barthélemy, St. Barthélemy

5.0 out of 5 average rating, 89 reviews

Casa Dolores

With your feet in the sand, less than a minute from the sea, La Casa Dolorès is the perfect place for a complete change of scenery and an ideal stay. Feet in the sand, in less than one minute from the sea, Casa Dolorès is the perfect place for a wonderfull stay on our beautifull island.

Oct 15 – 22

R5,661 ZAR per night

Superhost

Villa in Booby Hill, Bonaire, Sint Eustatius and Saba

4.97 out of 5 average rating, 36 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.

Mar 1 – 8

R9,877 ZAR per night