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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.

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
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, 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!

Top Guest favourite
A spa tub is set on a wooden deck, offering views of lush greenery and distant hills. Nearby, a small dining table with two chairs is positioned, inviting relaxation and outdoor dining. The sky above features scattered clouds, enhancing the serene atmosphere.
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 spacious terrace features a dining table and seating area, surrounded by lush greenery. A hammock is suspended nearby, inviting relaxation. The private pool glimmers under the evening sky, highlighting the picturesque view of the bay and sunset beyond.
Bungalow in Deshaies
4.97 out of 5 average rating, 132 reviews

PINEAPPLE Bungalow sea view

Welcome to Carambole and Pineapple, your little corner of heaven nestled in the heart of the banana trees. This intimate set of 2 brand new bungalows offers magnificent views of the breathtaking Grande Anse Bay. Ideally located on a private property, 5 minutes walk from the beach, on the first heights of Deshaies, they will guarantee you change of scenery, privacy, calm and tranquility. Come and admire the sublime sunsets from your private pool by tasting a tasty planter

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, 144 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.

Top 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
An outdoor wooden deck features a table and a chair, overlooking a stunning view of Toiny's bay. The coastline curves gently into the ocean, with waves breaking along the shore. The sky is partly cloudy, enhancing the serene atmosphere of the landscape.
Villa in Toiny
4.99 out of 5 average rating, 125 reviews

Surfin' Bird

Overlooking Toiny's bay surf spot, located at only 20 minutes from Gustavia, the city of glitter, golds and yachts, this 2 bedrooms villa is perfect for who wants to relax, reconnect with nature and enjoy simple island's life. With its simple design and authentic comfort, Surfin Bird villa is the best spot to access real Saint Barth: astonishing lanscape, cool breeze, colorful natural light, nice surf spots, welcoming people, Créole/French food and culture…)

Top Guest favourite
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 .

Popular amenities for Leeward Islands holiday rentals