Some info has been automatically translated. Show original language

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.

1 of 1 pages1 / 1
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
5.0 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
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.

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
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!

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

110 m² accommodation with magnificent views of the Caribbean Sea and Montserrat Island. The accommodation at the bottom of a villa is entirely private and has 3 bedrooms, 2 of which have access to a large bathroom. The third bedroom is equipped with a private bathroom with a massage bathtub. All bedrooms come equipped with large king size beds, 65" smart TV, fiber Internet. Living room with kitchen open to the terrace. End-of-stay cleaning and daily cleaning included in the price.

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.

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!

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

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
Cottage in Sainte-Rose
4.96 out of 5 average rating, 71 reviews

La Source Ecolodge

Chic, Natural & Tropical Serenity. La Source Ecolodge is an eco-friendly lodge where lush tropical nature meets chic comfort for a unique experience. Enjoy an elegant space of around 100 m² with a kitchen-bar, double bedroom, outdoor shower with sea view, and a punch bowl (river-water basin, natural water temperature) on the sea-facing terrace. High-speed Starlink WiFi throughout the property. Welcome guide sent upon booking. Cleaning fees included.

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 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
4.97 out of 5 average rating, 304 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