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Holiday houses in Leeward Islands

Find and book unique accommodation on Airbnb

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, 127 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.

Top Guest favourite
The image captures a stunning aerial view of the estate nestled atop dramatic red rock cliffs, surrounded by lush greenery. The turquoise waters of the Atlantic Ocean crash against the rocky shoreline, showcasing the estate's secluded location on Dominica's northeast coast.
Home in Wesley
5 out of 5 average rating, 21 reviews

Eden's Gate Red Rocks Estate-AC-Laundry-Kitchen

Eden’s Gate Red Rocks Estate is a luxurious retreat on Dominica’s northeast coast perched on dramatic cliffs overlooking the Atlantic Ocean. This private estate includes Eden’s Gate Villa, a beautifully designed Villa with 1bed/1.5bath and stunning architecture, and Cottage on the Rocks, a charming 1bed/1bath apartment with magnificent ocean views. Enjoy luxurious furnishings, modern comforts, and breathtaking coastal scenery. Perfect for relaxation or adventure; it’s your own slice of paradise!

Top Guest favourite
A person enjoys the serene view from the edge of a plunge pool, overlooking the mountains and the Caribbean Sea. The surrounding lush greenery and the dramatic outline of the Pitons enhance the natural beauty of the setting under a clear blue sky.
Guesthouse in LC
4.96 out of 5 average rating, 191 reviews

Romantic hideaway The Lodge at Cosmos St Lucia

Magical open air Lodge for couples and nature lovers, away from busy hotels. Plunge pool and sun deck with views over the Pitons and Caribbean Sea. Studio-style accommodation with kitchen, sitting area, queen sized bed and private outdoor bathroom. Homemade continental breakfast included. Panoramic views, sustainable luxury, concierge, friendly responsive staff, housekeeping, parking. Additional services: private dining, spa treatments, private driver. 10 mins to Soufriere, beaches, activities.

Guest favourite
Villa in Woodford Hill
4.9 out of 5 average rating, 41 reviews

Leatherback villa, Turtle Beach Villas

Conveniently located 10 minutes from the airport, escape to a private beachfront villa offering modern luxury, ocean views, and total tranquility—walk onto the sand from your doorstep. Enjoy freshly prepared meal by a chef or choose to cook your own. Perfect for families seeking comfort, friends spending quality time together or couples looking for romance and peace. Relax by your pool or one of the island's most beautiful beaches. Experience a warm hospitality designed for rest and connection.

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, 179 reviews

Etoile du Nord

ETOILE DU NORD est située face à la plage de Flamand , dont vous pourrez profiter de la vue exceptionnelle depuis chaque recoin de la villa moderne, fonctionnelle, elle est idéale pour un couple ou une famille avec de grands enfants qui apprécieront l'indépendance de la seconde chambre située au niveau inférieur. Il suffit de traverser la route pour accéder à la plage, que ce soit pour un bain matinal au soleil levant, une journée de farniente, ou une ballade du soir le long de la baie .

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, 198 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
4.87 out of 5 average rating, 218 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
Villa in Saint Andrew Parish
4.89 out of 5 average rating, 36 reviews

Escape Villa with private pool

Nestled in a lush jungle setting on Calibishie Beach, next to Red Rocks and the Chocolate Factory, this villa offers stunning Caribbean Sea views and a peaceful island escape. Two air-conditioned king suites each feature an en-suite bathroom with direct access to a private plunge pool. Relax by the infinity pool, al fresco dinning, unwind on the spacious covered terrace, or enjoy the fully equipped kitchen, comfortable living room, Smart TV, Wi-Fi while surrounded by nature.

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, 268 reviews

Lodge Rosewood atypique avec vue mer

"LODGE ROSEWOOD" : Au coeur d'un jardin tropical avec vue sur la mer des caraïbes et la montagne. 🤩Logement de charme pour 2 personnes.🥰 1 chambre double (lit 160x200 ou 2 lits 80x200) , salle d'eau, wc, cuisine, coin repas, deck avec chaises longues. Un planteur et accras de bienvenue vous sont offerts Masques, tubas, palmes à disposition, si besoin. Boite à livres. Le lodge Rosewood n'est plus disponible sur vos dates, vous pouvez consulter l'annonce du "COUNTRY LODGE" 😉

Top Guest favourite
A spacious terrace features a relaxing catamaran net, inviting rest with panoramic views of the sea and surrounding landscape. A potted plant adds a touch of greenery. Comfortable seating is provided by a nearby chair, enhancing the outdoor experience.
Home in Vieux-Habitants
4.98 out of 5 average rating, 98 reviews

Panorama Kréyòl : Bungalow

Découvrez Panorama Kréyòl, un bungalow sur pilotis offrant une vue spectaculaire sur la mer et les montagnes. Au cœur de la Basse-Terre, profitez d’un cadre en bois chaleureux, d’un jacuzzi privatif et d’une immersion totale dans la nature guadeloupéenne. Profitez de la proximité des plages idylliques, des randonnées vers la Soufrière, et des cascades. Climatisé et équipé d'une terrasse avec filet de catamaran, il offre confort et aventure. Un guide voyageur est inclus.

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
4.96 out of 5 average rating, 138 reviews

La Kabane secrète, piscine, SPA, lit king size

La Kabane Secrète est une véritable bulle d’amour conçue entièrement pour les couples. Ici, la nature tropicale et le confort exceptionnel d’un lodge bohème chic se rencontrent afin de vous ressourcer dans un moment hors du temps et de créer une expérience unique inoubliable. Dans un écrin de tranquillité et d’authenticité, la Kabane Secrète s’articule autour de la piscine et du jacuzzi, dans une atmosphère intérieur/extérieur qui invite à la détente et à la relaxation.

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, 160 reviews

Villa Pierre: A Luxury Hidden Gem in Saint Lucia

"EXPECT TO BE ABSOLUTELY BLOWN AWAY..." Tiffany, Tennessee, USA Summer Promotion until September 6th, 2026. 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. Effortless luxury. Unforgettable moments. Celebrate your special moments in a truly unforgettable way! All the amenities of a resort in a private villa!

Popular amenities for Leeward Islands holiday rentals