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Holiday houses in Leeward Islands

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Top-rated holiday rentals in Leeward Islands

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

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Top Guest favourite
An expansive view of the Caribbean Sea showcases deep blue waters, contrasting with the green landscape below. The island of Montserrat is visible in the distance against a clear blue sky, creating a serene and natural backdrop.
Apartment in Deshaies
4.97 out of 5 average rating, 119 reviews

Location Open Sky

Logement de 110m² avec vue magnifique sur la mer des Caraïbes et l'île de Montserrat. Le logement en bas d'une villa est entièrement privatif et dispose de 3 chambres dont 2 ont accès à une grande salle de bain. La troisième chambre est équipée d'une salle de bain privée avec une baignoire massante. Toutes les chambres sont équipées de grands lits King Size, smart TV 65", Internet fibre. Séjour avec cuisine ouverte sur la terrasse. Ménage de fin de séjour et ménage quotidien inclus dans le prix.

Guest favourite
Villa in Sapphire
4.95 out of 5 average rating, 123 reviews

VillaAura 15-25mins from UVF Airport & Attractions

Aura Villa sits majestically on a cliff overlooking a beautiful naturally flowing river. Waking up to the melodious chirping of birds is the highlight of every morning ! On evenings, lounge out on the pool deck and enjoy a magical night sky. Whether you choose to enjoy a refreshing swim in the crystal clear infinity pool or enjoy a warm bath under the rain shower, tranquility awaits you. The lush vegetation forest views which greets this villa from the valley top will leave you in complete awe!

Guest favourite
Bungalow in Deshaies
4.97 out of 5 average rating, 132 reviews

ANANAS Bungalow vue mer

Bienvenue à Carambole et Ananas, votre petit coin de paradis lové au coeur des bananiers. Cet ensemble intimiste de 2 bungalows tout neufs offre une vue magnifique sur l'époustouflante baie de Grande Anse. Idéalement situé sur une propriété privée, à 5 minutes à pied de la plage, sur les premières hauteurs de Deshaies, ils vous garantiront dépaysement, intimité, calme et tranquillité. Venez admirer les sublimes couchers de soleil depuis votre piscine privative en dégustant un savoureux planteur

Guest favourite
An open living area features wooden furniture complemented by vibrant cushions, accented by natural stone walls. Large windows invite daylight while offering views of the surrounding landscape. The space transitions smoothly to an outdoor pool area, creating an airy and connected atmosphere.
Villa in Soufriere
4.86 out of 5 average rating, 213 reviews

Villa Piton Caribbean Castle

Certified to host by St Lucia government. Super private and provides a secure and isolated retreat far from any crowds! We provide cooking service for breakfast lunch or dinner for an extra $20/person/meal. We incorporate heightened cleaning procedures and trained staff. Built by John DiPol, designer of the world-famous Ladera resort, Villa Piton elaborates on the open-aired concept providing breathtaking views everywhere! Extraordinary location and views that need to be seen in person!

Guest favourite
Home in Petit-Bourg
4.94 out of 5 average rating, 110 reviews

Gîte Kolin's view

KOLIN’S view, moderne et contemporain, est situé sur une propriété sécurisé privée avec parking. Il est entièrement équipé et ouvert sur l’extérieur avec mini piscine privative. Le site est également muni de citernes vous permettant de ne pas manquer d’eau. La ZAC à proximité vous donnera accès à toutes commodités. La situation géographique permet de profiter d’une vue montagne, d’accéder aux nombreuses cascades, randonnés, plages, spots de plongée, brasserie local, marché…

Guest favourite
A villa's outdoor area is framed by wooden details and lush greenery. A private plunge pool is visible alongside a terrace. Large glass doors afford a view into the interior of the home, enhancing the connection between indoor and outdoor spaces.
Villa in Soufriere
4.93 out of 5 average rating, 430 reviews

Serrana Villa -Contemporary $1M Piton View Retreat

At Serrana Villa, style and grace are clearly evident in every aspect of this sophisticated 1-level, 2BR/2BA home. Located in Soufriere, the quintessential attraction capital of St. Lucia, Serrana Villa offers sweeping panoramic views of the majestic Piton World Heritage Sites as well as the surrounding lush hills and mountains from the romantic plunge pool, the terrace, and even from the rooms of the villa itself is a joy to behold. Come follow us ! @serranavillastlucia

Top Guest favourite
Villa in Le Morne-Vert
4.99 out of 5 average rating, 230 reviews

Creole wooden cottage with hot tub for 4 people – TiLokal

TiLokal gîte is located at the foot of the Pitons du Nord, a UNESCO World Heritage Site. Access to the Coco River through the 3000 m2 garden planted with local trees and flowers. You're in the rainforest. Here, no need for air conditioning, the wooden construction, the blinds integrated into the windows and the place make it a naturally ventilated home. This is the ideal place to enjoy eco-friendly tourist activities: hiking, canyoning, sailing trips, diving, massages...

Guest favourite
A tiny house is situated on a hillside, surrounded by lush greenery and dense trees. The structure features a covered porch, offering a panoramic view of the hillside environment. Natural light is evident, highlighting the wooden exterior and tranquil setting.
Tiny home in Deshaies
4.96 out of 5 average rating, 197 reviews

Tuwana

Tiny House perched on a hill at 400 m altitude in the middle of a fruit garden. Accessible by a forest road in good condition. Quiet and secluded place between sea and mountain with a dominant view. Naturally cool and airy mosquito-free accommodation. Eco-friendly accommodation. Located 10 minutes from Leroux Beach 20 minutes from Malendure Beach 20 minutes from Grande Anse Beach Suitable for people who want to disconnect, rest or recharge.

Guest favourite
A private plunge pool is framed by natural stone walls and vibrant tropical plants. The clear blue water reflects the surrounding greenery, while steps lead into the pool. A splash of red from a nearby flower adds a touch of color to the peaceful setting.
Villa in Saint Andrew Parish
4.88 out of 5 average rating, 33 reviews

Escape Villa with private pool

This stunning private luxury villa is nestled in an exotic jungle setting. The villa is located on Calibishie beach next to the Red Rocks & Chocolate Factory. Each king bedroom opens to a private plunge pool from their ensuite bedrooms. The bedrooms are with Air conditioning. The private pool with an over sized covered outdoor patio gives view on the beautiful Caribbean ocean. The villa has an equipped kitchen, a living room with TV and wifi.

Guest favourite
A wooden terrace features three lounge chairs with bright orange towels, overlooking a sandy beach and shimmering blue ocean. Lush greenery surrounds the area, while a bright sky adds to the inviting atmosphere.
Home in Flamands
4.95 out of 5 average rating, 176 reviews

Etoile du Nord

ETOILE DU NORD is located opposite Plage des Flamands , from which you can enjoy the exceptional views from every corner of the villa modern, functional, it is ideal for a couple or family with large children who will enjoy the independence of the second bedroom located on the lower level. You just have to cross the road to get to the beach, either for a morning swim in the rising sun, a day of relaxation, or an evening stroll along the bay .

Top Guest favourite
A spacious open-air lounge area is surrounded by wooden beams and nature, offering panoramic views of the sea. Comfortable seating arrangements include black chairs and a large table. Potted plants enhance the natural setting, providing a relaxing atmosphere for enjoying the outdoor experience.
Cottage in Portsmouth, Saint John Parish, DM
4.97 out of 5 average rating, 299 reviews

HIDEAWAYs- Madé Cottage-Exotic Treehouse-Seaview

As seen on "10 Most Affordable Caribbean Destinations" Handcrafted, treehouse-style hillside cottage for up to 6 guests Conveniently located Panoramic sea views Surrounded by nature Upper Level Studio: The primary living space with Queen & single bed, ensuite bathroom, kitchenette, open-air lounge Lower Level: 2nd bedroom with Queen bed & optional IKEA cot, ensuite bath & large sundeck Ideal for couples, friends & family

Guest favourite
A cozy bedroom features natural wood paneling and a thatched ceiling, illuminated by soft light. A spacious bed is adorned with decorative pillows, and a bedside table crafted from wood adds to the rustic charm. A large sliding door leads to the outdoor space.
Home in Saint-François
4.97 out of 5 average rating, 121 reviews

The Secret Kabane, Pool, SPA, King Size Bed

The Secret Hut is a true bubble of love designed entirely for couples. Here, tropical nature and the exceptional comfort of a bohemian chic lodge meet to rejuvenate you in a timeless moment and create a unique and unforgettable experience. In a haven of tranquility and authenticity, the Secret Kabane is built around the swimming pool and jacuzzi, in an indoor/outdoor atmosphere that invites you to relax and unwind.

Popular amenities for Leeward Islands holiday rentals