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Holiday rentals in Windward Side

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Top-rated holiday rentals in Windward Side

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

Guest favourite

Home in Windwardside, Bonaire, Sint Eustatius and Saba

4.88 out of 5 average rating, 33 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.

2–9 Dec

£222 per night
Guest favourite

Holiday home in Windwardside, Bonaire, Sint Eustatius and Saba

4.96 out of 5 average rating, 27 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.

2–9 Aug

£131 per night
Guest favourite

Loft in Gustavia, St. Barthélemy

5.0 out of 5 average rating, 28 reviews

Loft Harbour

Ce logement affiche un style résolument unique. Venez vous prélasser dans un environnement exceptionnel, au coeur de Gustavia. Ce loft, doté d'un jacuzzi vous permettra de profiter de la vue sur les Yatchs et le port. Vous pourrez profiter du coeur effervescent de Gustavia. This accommodation has resolutely unique style. Come and relax in an exceptional environment in the heart of Gustavia. This loft with a jacuzzi will allow you to enjoy the views of the yatchs and the harbor.

1–8 Oct

£362 per night

Popular amenities for Windward Side holiday rentals

Other great holiday rentals in Windward Side

Guest favourite

Flat in BL, St. Barthélemy

5.0 out of 5 average rating, 26 reviews

Amazing view 2 min walk to the beach!

13–20 Oct

£357 per night
Guest favourite

Home in Lorient, Saint Barthélemy

5.0 out of 5 average rating, 28 reviews

Villa Yvantino Beachfront (Bedrooms 2ch)

30 May – 6 Jun

£837 per night
Guest favourite

Home in gustavia, St. Barthélemy

5.0 out of 5 average rating, 42 reviews

VILLA ANGEL SUNSET

14–21 Mar

£371 per night
Superhost

Villa in St Barthelemy , St. Barthélemy

5.0 out of 5 average rating, 21 reviews

Villa Jali

25 Jul – 1 Aug

£661 per night
Guest favourite

Flat in BL

4.91 out of 5 average rating, 64 reviews

Seaduction

22–29 Nov

£318 per night
Guest favourite

Flat in Corossol

4.91 out of 5 average rating, 54 reviews

Corossol studio 2 minutes walk from the beach

14–21 Jul

£125 per night
Guest favourite

Villa in BL, St. Barthélemy

4.96 out of 5 average rating, 52 reviews

Saint Barth Colombier

16–23 Jan

£806 per night
Guest favourite

Guest suite in BL, St. Barthélemy

4.98 out of 5 average rating, 51 reviews

Independent entrance studio and kitchen in Flamands

18–25 Jun

£140 per night
Superhost

Villa in BL

4.93 out of 5 average rating, 27 reviews

VILLA RÉMI view of Gustavia harbor

19–26 Jan

£939 per night
Guest favourite

Apartment in Saint-Jean, Saint Barthélemy

5.0 out of 5 average rating, 28 reviews

One bedroom apartment ideally located in St Jean

28 Jul – 4 Aug

£207 per night
Guest favourite

Flat in Gustavia

4.92 out of 5 average rating, 88 reviews

* Charming studio for 2 people in Colombier *

30 Aug – 6 Sept

£132 per night
Guest favourite

Apartment in Saint-Jean, Saint Barthélemy, St. Barthélemy

4.87 out of 5 average rating, 23 reviews

New apartment, sea view, infinity pool.

8–15 May

£626 per night

Destinations to explore