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Vacation rentals in Leeward Islands

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Top-rated vacation rentals in Leeward Islands

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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, 128 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.

LocationFamilyDecor

Top guest favorite
Villa in Woodford Hill
5 out of 5 average rating, 47 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.

FamilyValueTV

Guest favorite
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
4.89 out of 5 average rating, 202 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.

LocationFamilyNearby

Guest favorite
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, 219 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!

ValueLocationHiking

Top guest favorite
A coastal view is framed by an open doorway, presenting a serene scene of the ocean and the island of Nevis. Two wicker chairs are positioned on a balcony, while lush greenery and a sailboat enhance the picturesque setting.
Place to stay in Southeast Peninsula
4.99 out of 5 average rating, 74 reviews

Right on the Caribbean Beach! Peaceful waves.

Our Turtle Beach Cottage is right on the beach! Fabulous views to our sister island of Nevis, the ocean and reef! Watch pelicans dive, sting rays leap and turtles bobbing their head up to catch a breath! Curious vervet monkeys may pay a visit, morning doves wake you with their quiet cooing and yellow crested night herons perch in our mangrove trees. Peace and quiet minutes away from excellent restaurants and activities. Beach combing easy walks and great hikes in our area.

LocationValueSleep quality

Guest favorite
Bungalow in Saint Barthélemy
5 out of 5 average rating, 14 reviews

Star - Ocean view villa with private plunge pool

The <b>bungalow in Saint Barthélemy</b> has 1 bedrooms and capacity for 2 people. <br>Accommodation of 409 ft², It has views of waterfront and the garden. <br>The accommodation is equipped with the following items: garden, garden furniture, fenced garden, 108 ft² terrace, iron, safe, internet (Wi-Fi), hair dryer, balcony, heat pump, air-conditioned, swimming pool private, heated swimming pool private, open-air parking in the same building, 1 electric anti-mosquito device, 2 TVs.

ValueLocationHospitality

Top guest favorite
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, 101 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.

LocationSleep qualityAccess

Top guest favorite
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, 271 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 😉

LocationValuePool

Guest favorite
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, 181 reviews

North Star

ETOILE DU NORD is located facing Flamand beach, from which you can enjoy the exceptional view from every corner of the villa modern, functional, it is ideal for a couple or family with large children who will appreciate the independence of the second bedroom located on the lower level. All you have to do is cross the road to get to the beach, whether it's for a morning swim in the rising sun, a lazy day, or an evening stroll along the bay .

FamilyValueParking

Guest favorite
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, 142 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.

ValueLocationAccuracy

Guest favorite
Home in Le Moule
4.89 out of 5 average rating, 54 reviews

OlympeLodge | Quiet escape • Private pool

OlympeLodge, an ideal haven of peace for a relaxing stay. The accommodation is independent, functional and comfortable, located near the center. The location allows easy access to beaches, shops and main roads. We welcome you in a quiet environment, with swimming pool and private garden, enough to relax in privacy. We will be happy to contribute to your escape.

LocationFamilyKitchen

Top guest favorite
A sunlit deck features comfortable loungers with a straw hat resting on one. Lush greenery surrounds the space, while the iconic Pitons rise majestically in the background against a vibrant blue sky and tranquil sea.
Villa in Soufriere
4.98 out of 5 average rating, 153 reviews

La Batterie Villa • Boutique Villa • Amazing Views

Tucked away in the prestigious Anse Chastanet / Jade Mountain area of Soufrière, the Villa is a private retreat designed for relaxation, comfort, and unforgettable views. Perched 300 feet above the Caribbean Sea and facing the iconic Pitons, the villa enjoys cooling island breezes and panoramic scenery that never fails to impress.

FamilyValueAir conditioning

Popular amenities for Leeward Islands vacation rentals