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Holiday rentals 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.
Flat in Deshaies
4.96 out of 5 average rating, 112 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, 16 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 scenic balcony view features a hammock and lush greenery overlooking the valley. Majestic mountains are visible in the distance against a colorful sunset sky, enhancing the tranquil atmosphere of the surrounding landscape.
Tiny home in Vermont
4.91 out of 5 average rating, 161 reviews

Spirit of the Valley - Strong's House

Pine house on rainforest edge Queen Bed Superior mattress Mosquito net Outstanding views valley/sea/gardens WIFI Comfortable, rustic, clean Tranquil setting Can be very windy Good for hikers, birders, yogis Daybed Hike: can hear parrots from cottage Vermont Trail Hills above Bush Bar 10mins-1hr Table Rock, Moonmarket 1 hr 3️⃣ Ponds Waterfalls 2hrs Drive: Superb snorkelling site 45 mins. Provided: Soap, handmade with coconut oil and no fragrance Salt, pepper Coffee 1 towel each Cafetiere

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
4.97 out of 5 average rating, 129 reviews

ANANAS Bungalow vue mer

Bienvenue à Carambole et Ananas, votre petit coin de paradis lové au coeur des bananiers. Cet ensemble intimiste de 2 bungalows tout neufs offre une vue magnifique sur l'époustouflante baie de Grande Anse. Idéalement situé sur une propriété privée, à 5 minutes à pied de la plage, sur les premières hauteurs de Deshaies, ils vous garantiront dépaysement, intimité, calme et tranquillité. Venez admirer les sublimes couchers de soleil depuis votre piscine privative en dégustant un savoureux planteur

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
4.91 out of 5 average rating, 191 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, 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 view from a shaded terrace features two lounge chairs positioned on a wooden deck, overlooking a sandy beach. The calm water reflects the blue sky and distant hills, while boats are anchored nearby. Palm trees sway gently, enhancing the tranquil coastal atmosphere.
Home
4.86 out of 5 average rating, 209 reviews

In the Bay of Saints, right by the water

With your feet in the water on a white sandy beach, our house is located in Terre-de-Haut in the Saintes archipelago (Guadeloupe), nestled in the heart of its wonderful bay and in the typical fishermen's district of Fond de Curé. Close to all amenities, no need to rent a vehicle for your shopping or to go to the beach, everything is on site. The house is 90 m2 in duplex with a 30 m2 terrace overlooking the sea. Comfort, quiet and beauty will fill you with happiness.

Top guest favourite
An inviting living area features a dark leather sofa with a decorative cushion, complemented by a rustic wooden side table. Large glass doors open to a spacious outdoor deck, while warm wood flooring enhances the natural light in the space.
Tiny home in Deshaies
4.97 out of 5 average rating, 187 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, 171 reviews

Etoile du Nord

ETOILE DU NORD is located opposite Flemish Beach, 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 big children who will appreciate the independence of the second bedroom located on the lower level. Just cross the road to get to the beach, whether it's a morning bath in the rising sun, a day of laziness, 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, 293 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
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, 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