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Holiday houses in Leeward Islands

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Top-rated holiday rentals in Leeward Islands

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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
4.96 out of 5 average rating, 113 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.

Superhost
A spacious veranda offers panoramic views of the Caribbean Sea and surrounding mountains. The railing provides a clear line of sight to the vibrant landscape, while the open area is designed for relaxation and enjoyment of the serene environment.
Home in Saint Joseph
5 out of 5 average rating, 13 reviews

Waitukubuli Heaven, Breathtaking Views, Near Beach

Waitukubuli Heaven is a Caribbean retreat in Sayers Estate, St. Joseph, featuring 3 bedrooms and 2.5 baths with stunning 180-degree views of the Caribbean Sea and mountains. Guests enjoy easy access to a pristine beach and can unwind on a private balcony while watching breathtaking sunsets. The home combines modern simplicity with upscale amenities, fully equipped kitchen, Wi-Fi, and overhead fans, ensuring comfort and convenience. It's an ideal getaway for nature lovers seeking adventure.

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, 212 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
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, 427 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
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, 224 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, 102 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

Top Guest favourite
A comfortable seating area is positioned on a covered terrace, overlooking the vast Caribbean Sea. Cushions in warm tones adorn the wooden bench, with greenery visible in the background and a clear blue sky enhancing the serene view.
Home in Rifflet
4.94 out of 5 average rating, 142 reviews

Prestigious villa with sea view – Deshaies

House, 180° view of the Caribbean Sea. Beach 50 meters away. Fully equipped kitchen (stove, microwave, dishwasher, washing machine etc...), air conditioning in the bedrooms, large 50 m2 veranda. Open bar on veranda. Deck with solarium and barbecue. Spacious rooms with storage. 2 bathrooms, 2 powder rooms. Living room and dining area on veranda. Free WiFi (fiber) Nearby busy road causing car noise during the day. This inconvenience disappears in the evening and at night.

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, 189 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, 175 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, 294 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
Home in Saint-François
4.96 out of 5 average rating, 111 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