Vacation rentals in Windward Side

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Top-rated vacation rentals in Windward Side

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Guest favourite

Home in Gustavia, St. Barthélemy

4.97 out of 5 average rating, 35 reviews

3 bedrooms at pointe Milou , concierge , best view

pointe milou is the place to be in st barth for your vacation . this 3 bedrooms villa have everything you need best sunset , swimming pool, BBQ, home cinema screen, backgammon table ,, full concierge service This is the only place in st barth where construction are not permit from November to may to protect guest from noice I’m the owner of the place . I’m super host for 6 years. And one of the guest favorite. On rbnb. Only 30 house in the island I will be here to take care of everything

Jun. 4 – 11

$1,302 CAD per night

Guest favourite

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.

Jul. 1 – 8

$381 CAD per night

Guest favourite

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.

Nov. 17 – 24

$224 CAD per night

Guest favourite

Home in Saint-Barthélemy, St. Barthélemy

4.97 out of 5 average rating, 119 reviews

Etoile du Nord

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

$400 CAD per night

Guest favourite

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

Nov. 16 – 23

$421 CAD per night

Guest favourite

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.

Oct. 12 – 19

$805 CAD per night

Guest favourite

Condo in St. Barthelemy, St. Barthélemy

4.98 out of 5 average rating, 47 reviews

Cadence- Apartment

Welcome to the Cadence Residence. Located in the heart of the island, in the district of Camaruche, this new apartment of 62m2 located in a new residence on the ground floor offers many advantages. It has a large terrace, a double bedroom, a large bathroom with double sink and walk-in shower as well as a fully equipped kitchen and a living area. Its modern and tropical decoration, will make you travel!

Jun. 3 – 10

$233 CAD per night

Guest favourite

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 completely tastefully renovated, in the heart of St Jean, a 2-minute walk from the beach, restaurants and shops. The accommodation is fully equipped, large kitchen, 2 smart TVs, internet, sound systems, etc... Let yourself be seduced by the cozy and soothing atmosphere with views of the sea, the beach and the neighboring islands.

Dec. 4 – 11

$881 CAD 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.

Jun. 13 – 20

$1,229 CAD per night

Guest favourite

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

$242 CAD per night

Guest favourite

Home in Lorient, Saint Barthélemy, St. Barthélemy

5.0 out of 5 average rating, 90 reviews

Casa Dolorès

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.

Feb. 25 – Mar. 4

$534 CAD 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.

Aug. 17 – 24

$701 CAD per night