Vacation rentals in Windward Side

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Top-rated vacation rentals in Windward Side

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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. 6 – 13

$387 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.

May 22 – 29

$209 CAD per night

Guest favourite

Cottage in Saint Kitts and Nevis, St. Kitts & Nevis

5.0 out of 5 average rating, 64 reviews

Ocean Song Charming Cottage

Situated overlooking the quiet Turtle Beach Cove on the renowned South East Peninsula is a very peaceful and private charming cottage. Artistic Cabin on the hillside with stunning ocean views! Enjoy your morning coffee while watching the pelicans dive for their breakfast. Keep an eye out for sea turtles on the amazing reef just below the cottage. Hummingbirds buzz around you in the gardens. Have a sunset drink and be amazed at the outstanding view of Nevis!

Sep. 20 – 27

$356 CAD per night

Guest favourite

Home in Saint-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

$408 CAD per night

Guest favourite

Apartment in BL

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

Oct. 5 – 12

$423 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.

Sep. 22 – 29

$808 CAD per night

Guest favourite

Condo in Saint-Bathélémy, St. Barthélemy

5.0 out of 5 average rating, 58 reviews

Cadence- Studio

Welcome to the Cadence Residence. Located in the heart of the island, in the district of Camaruche, this new apartment of 45m2 located in a new residence on the ground floor offers many advantages. 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 decoration, will make you travel!

Jul. 2 – 9

$251 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.

Feb. 12 – 19

$1,599 CAD per night

Guest favourite

Home in Lorient, Saint Barthélemy, St. Barthélemy

5.0 out of 5 average rating, 91 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.

Mar. 6 – 13

$536 CAD per night

Guest favourite

Villa in Booby Hill, Bonaire, Sint Eustatius and Saba

4.97 out of 5 average rating, 37 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.

Feb. 20 – 27

$712 CAD per night

Guest favourite

Cabin in Windwardside, Bonaire, Sint Eustatius and Saba

4.94 out of 5 average rating, 16 reviews

El Momo Cottages (cottage with kitchenette)

High upon a green, Caribbean mountain the place to 'free your mind' awaits. Nature lovers who enjoy tropical flowers, palm trees, ocean views and warm hospitality will find El Momo to be the perfect retreat. You will feel like Robinson Crusoe.

Apr. 14 – 21

$170 CAD per night