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Vacation rentals in Leeward Islands

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Top-rated vacation rentals in Leeward Islands

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Guest favorite
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
4.95 out of 5 average rating, 177 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 favorite
The image features a wooden deck with two lounge chairs positioned for relaxation. A cabin with wooden shingles and wide steps leads into the greenery. Large windows and balcony railing provide a panoramic view of the surrounding trees and natural landscape.
Cabin in Sawcolts Village
4.98 out of 5 average rating, 160 reviews

Tranquil Farm - Secluded Woodland Eco Cabin

The wooden shingled cabin is totally off the grid. To reach the cabin is a short walk up through a small wood on a narrow winding path from the parking area. Built on stilts the cabin over looks farmland and woods with a long view down the valley to the hills of English Harbour. The cabin has a large bedroom with wooden four poster bed with mosquito net. Barn doors open onto a side balcony, an open air bathroom with rain water shower heated by solar and a full kitchen. Wonderful night skies.

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, 175 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.

Superhost
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
4.85 out of 5 average rating, 193 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 favorite
An open-air pavilion overlooks the calm sea, featuring a large infinity pool with a wooden deck. A single blue bean bag chair rests on the edge, facing the expansive horizon. Lush palm trees frame the serene view under a clear sky with distant clouds.
Villa in Bolands
4.97 out of 5 average rating, 33 reviews

Unique Caribbean Secluded Open Air Villa 1 Bedroom

This very secluded villa consists of open-air bungalows by the sea. Stairs lead to a stony, private beach. The kitchen, dining hall, and lounge are separate. Above these is the master bedroom bungalow with an infinity pool, large patio, outdoor and indoor baths, showers, and kitchenette. The villa, in the southern part of Jolly Harbour, has all the amenities such as shops, beauty salons, restaurants, and sports facilities. This property is listed three times as a 1, 2, and 3 bedroom.

Top guest favorite
A spacious sleeping area features a handcrafted wooden bed topped with floral bedding, complemented by sheer mosquito nets. Natural light filters through wooden slats, illuminating a soft rug on the floor. A small reading chair is positioned nearby, enhancing the cozy ambiance of the cottage.
Cabin in Portsmouth
4.99 out of 5 average rating, 243 reviews

HIDEAWAYS-FouFou Cottage Open-air Paradise Seaview

"FouFou Cottage" Seen as "10 Most Affordable Caribbean Destinations" & Safe in Nature CERTIFIED. Sustainably handcrafted, private, self-contained treehouse-style cottage with spacious verandah perfect for birdwatching & relaxing. A natural sanctuary with breathtaking seaviews & cool mountain breezes. A unique, 2 level Open Air, Eco-cottage with Modern Ensuite Bath & Kitchenette. Quiet & Conveniently located less than a mile to sites, restaurants, shops & beaches of Portsmouth.

Top guest favorite
A sweeping view captures the vibrant turquoise waters of the coastline, framed by lush green hills. Islands dot the horizon under a clear blue sky, while the wooden railing in the foreground provides a picturesque viewing point of the landscape.
Guesthouse in BL
4.98 out of 5 average rating, 176 reviews

les Ramiers

Spend your holidays at Villa les Ramiers, where the sun is with you from sunrise and throughout the day. The accommodation is independent, not overlooked, with its small kitchen and terrace overlooking the pool, a top-deck to enjoy the sunrise, a large bedroom overlooking the covered patio with lounge area with sea view. Located on the well-ventilated heights with stunning views of Petite Anse. Private parking is located next to the Villa. Welcome!

Guest favorite
An outdoor lounging area features a comfortable sofa and a wooden table, set against a backdrop of palm trees and a sparkling pool. A hammock hangs nearby, with sweeping views of the Caribbean Sea and blue sky dotted with clouds.
Villa in Case-Pilote
5 out of 5 average rating, 13 reviews

New! Luxury Caribbean villa with pool and sea view

Wonderful view of the Caribbean Sea! Very beautiful villa, quiet and relaxing, located in a more popular residence, which overlooks the large bay. The awakenings are bright and the sunsets are breathtaking. The first sea bath is a 4-minute drive. The villa is tastefully furnished, quality materials and fully equipped. Salt Pool. Garden. BBQ. Ideal location to shine all over the island. Secure private parking for 2 cars. Supermarket at 5 minutes.

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
4.98 out of 5 average rating, 61 reviews

The Secret Hut, pool, HOT TUB, king size bed

The Secret Kabane is a true love bubble designed entirely for couples. Here, the tropical nature and exceptional comfort of a chic bohemian lodge meet to recharge your batteries in a timeless moment and create an unforgettable unique experience. In a setting of tranquility and authenticity, the Secret Kabane revolves around the swimming pool and jacuzzi, in an indoor/outdoor atmosphere that invites relaxation and relaxation.

Guest favorite
A private infinity pool is situated on a wooden deck, surrounded by lounge chairs and an umbrella. The clear blue waters of Deep Bay are visible in the background, framed by lush greenery and a serene sky. A nearby dining area with a table enhances the outdoor space.
Home in Galley Bay
5 out of 5 average rating, 7 reviews

Polaris villa. Stunning view, pool, beach nearby.

Polaris villa offers an exclusive location and stunning views of Deep Bay. The Galley Bay beach is within walking distance. The lovely private infinity pool with deck and barbeque area is perfect for relaxation. The 2 bedrooms with AC and attached bathrooms have circular windows with stunning views of the bay. The veranda is spacious and overlooking the water. Ideal for a couple who need extra privacy or for a group of 4.

Guest favorite
A wooden dining table with four slatted chairs is positioned on a covered terrace. The scene is enhanced by a view of the ocean and palm trees, with the sun setting in the background, casting warm hues across the sky.
Condo in Saint John's
4.89 out of 5 average rating, 147 reviews

Halcyon Dream

This apartment enjoys the best location in Halcyon Heights Condominium, a charming private community consisting of one and two story buildings surrounded by lush gardens and beautiful landscaping that wrap around a large pool overlooking the Caribbean Sea. Onsite and free parking. Convenient also to restaurants and bars and only a few minutes away from beautiful Dickenson Bay.

Top guest favorite
A spacious balcony features comfortable seating, offering a clear view of the ocean and lush greenery. Large glass doors reflect the serene coastal landscape, enhancing the sense of openness and natural light within the living space.
Apartment in Bouillante
5 out of 5 average rating, 63 reviews

Vaneïa: Exceptional duplex, panoramic sea view

Spectacular Sea View: Relax and enjoy breathtaking sunsets from the comfort of our apartment. The panoramic sea view from our balconies is simply unforgettable. Our premium accommodation is designed for your comfort. With modern amenities, a fully equipped kitchen, an elegant suite and spacious living areas, you'll feel right at home from the moment you arrive.

Popular amenities for Leeward Islands vacation rentals