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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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Top Guest favourite
A private terrace with wooden decking features a small pool, offering views of the bay and surrounding hills. A table and chairs are positioned nearby, creating a serene outdoor space. Bright blue skies and calm waters enhance the relaxing atmosphere.
Cottage in Les Anses-d'Arlet
4.97 out of 5 average rating, 176 reviews

Mini Villa 1Ch Private Pool Sea View and Sea Access

Turtle Bay Rental Accommodation Grande Anse - Martinique Elevated one-bedroom mini villa offering panoramic views of the sea and the countryside. Sea access 50 metres away on foot. This beach is renowned for the many green turtles that can be seen while snorkelling with a mask and fins all year round. Comprises an air-conditioned bedroom with a mosquito net, a shower room with a toilet, a fully equipped kitchen on the covered terrace, and a 2 m x 3 m private pool on the open-air terrace. TiSable restaurant 50 metres away and small shops 500 metres away.

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, 124 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, 19 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
Villa in Woodford Hill
5 out of 5 average rating, 39 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, 197 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
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, 105 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 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, 97 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 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, 202 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, 266 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, 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, Saint John Parish, DM
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