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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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Guest favourite
A private pool with crystal-clear water reflects the blue sky, leading to a wooden deck. The entrance to the villa features floor-to-ceiling glass doors, providing an inviting view of the interior and the surrounding greenery.
Villa in Vieux Fort
4.89 out of 5 average rating, 159 reviews

Villa Pierre: A Luxury Hidden Gem in Saint Lucia

"EXPECT TO BE ABSOLUTELY BLOWN AWAY..." Tiffany, Tennessee, USA FREE Airport Pick-up and a complimentary freshly prepared home-cooked meal upon arrival on all bookings! In addition: Stay 7 nights and “Experience the Exceptional” with a one FREE dining experience with a 5 star Private chef. Enjoy an exquisite 4 course meal carefully crafted and served in the privacy of the villa. Celebrate your special moments in a truly unforgettable way! All the amenities of a resort in a private villa!

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!

Superhost
The villa is nestled on a hillside, showcasing a modern design with a grey roof and stone accents. An infinity pool reflects the surrounding greenery, while large glass doors create a seamless transition between indoor and outdoor spaces.
Villa in Soufriere
4.9 out of 5 average rating, 194 reviews

Enclave Villa V3 -Overlooking Pitons & Ocean ! Wow

Enclave Villa V3 is a 2 bedroom villa with much to offer. This elegant property sleeps 4 and boasts such amenities as a Infinity pool off of both the master bedrooms. Located in Soufriere, the quintessential attraction capital of St. Lucia, Enclave 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.

Guest favourite
Villa in Soufriere
4.86 out of 5 average rating, 214 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…

Top Guest favourite
A spacious wooden deck offers a hot tub with a scenic view, bathed in warm sunlight during sunset. Surrounding lush greenery and a tropical atmosphere enhance the inviting setting of the villa.
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 shaded balcony area is furnished with comfortable seating and a central coffee table. Lush greenery surrounds the space, while expansive ocean views are visible through the railing. Light curtains gently sway in the breeze, enhancing the serene outdoor atmosphere.
Cottage in Toucari Bay
4.92 out of 5 average rating, 103 reviews

Coconut Cottage - Stunning Oceanview

Coconut Cottage was built in 2013 by local craftsmen from the village of Toucari. The structure is all timber with tiled floors and many windows for natural lighting. Stunning ocean views await you! There is a short walk downhill to a lovely beach, local restaurant and a quaint fishing village. Snorkeling, kayaking and swimming are just a few of the activities that await you! Located 10 minutes from Portsmouth where there is shopping and amenities @coconutcottagedominica

Guest favourite
A wooden deck is shown, featuring two rustic chairs positioned around a unique tree stump table. A lush green landscape surrounds the area, with trees providing a natural backdrop and a glimpse of the ocean visible in the distance.
Tiny home in Deshaies
4.96 out of 5 average rating, 198 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.

Top Guest favourite
A serene outdoor area is depicted, featuring a wooden deck adorned with two sun loungers. A large shade umbrella provides relief from the sun. Lush greenery surrounds the space, with rolling hills visible in the background under a clear sky.
Bungalow in Vieux-Habitants
4.99 out of 5 average rating, 265 reviews

Atypical Rosewood Lodge with Sea View

"LODGE ROSEWOOD": In the heart of a tropical garden overlooking the Caribbean Sea and the mountains. 🤩Charming accommodation for 2 people.🥰 1 double bedroom (160 x 200 bed or 2 80 x 200 beds), shower room, toilet, kitchen, dining area, deck with deckchairs. A welcome planter and snacks are offered Masks, snorkels, fins available, if needed. Book box. The Rosewood lodge is no longer available on your dates, you can check out the "COUNTRY LODGE" listing 😉

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

Popular amenities for Leeward Islands holiday rentals