Vacation rentals in Leeward Islands

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Top-rated vacation rentals in Leeward Islands

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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.

Guest favorite

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, 116 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

Guest favorite

A private pool is featured on a spacious terrace, with surrounding wooden accents. The calm blue water reflects the sky, providing a serene view of the Caribbean Sea and coastal scenery. Natural light illuminates the area, enhancing the tranquil atmosphere.

Tiny home in Le Gosier

4.96 out of 5 average rating, 140 reviews

DEEP BLUE apartment, sea view – private pool

The DEEP BLUE apartment is located in the heart of the village of Le Gosier in a small residence of 10 independent accommodations organized in terraces. It offers an exceptional sea view over the islet of Gosier, Les Saintes, Marie Galante and the coasts of Basse Terre. You will enjoy its furnished terrace with a private swimming pool of 2m x 5m. The apartment has been renovated and we have put our soul into this project so that you can live the Caribbean experience. FREE PARKING. Free WIFI.

Top guest favorite

A private patio is visible with two colorful Adirondack chairs, one yellow and one orange, positioned towards a stunning view of the water. Lush greenery surrounds the area, and boats can be seen floating in the serene bay under a bright blue sky.

Apartment in Ratho Mill

4.98 out of 5 average rating, 181 reviews

Coconut Lookout | Stunning views and steps to sea

Coconut Lookout nestles amongst the coconut palms with breathtaking views of both the Atlantic Ocean and Caribbean sea. Just below the apartment there are 80 steps that give access to safe swimming in Blue Lagoon. This stylish, air conditioned studio apartment consisting of a bedroom, with double bed, bathroom and kitchenette. The large private patio, with sun and shade, is a great place to relax Please note bookings for infants or children are not allowed due to the cliffside location.

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

4.87 out of 5 average rating, 190 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!

Superhost

A villa's outdoor area is framed by wooden details and lush greenery. A private plunge pool is visible alongside a terrace. Large glass doors afford a view into the interior of the home, enhancing the connection between indoor and outdoor spaces.

Villa in Soufriere

4.93 out of 5 average rating, 405 reviews

Serrana Villa -Contemporary $1M Piton View Retreat

At Serrana Villa, style and grace are clearly evident in every aspect of this sophisticated 1-level, 2BR/2BA home. Located in Soufriere, the quintessential attraction capital of St. Lucia, Serrana 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. Come follow us ! @serranavillastlucia

Top guest favorite

A spacious wooden deck offers a hot tub with a scenic view, bathed in warm sunlight during sunset. Surrounding lush greenery and a tropical atmosphere enhance the inviting setting of the villa.

Villa

4.98 out of 5 average rating, 186 reviews

Creole wooden cottage with jacuzzi – Le TiLokal

TiLokal gîte is located at the foot of the Pitons du Nord, a UNESCO World Heritage Site. Access to the Coco River through the 3000 m2 garden planted with local trees and flowers. You're in the rainforest. Here, no need for air conditioning, the wooden construction, the blinds integrated into the windows and the place make it a naturally ventilated home. This is the ideal place to enjoy eco-friendly tourist activities: hiking, canyoning, sailing trips, diving, massages...

Guest favorite

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, 144 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 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, 250 reviews

Atypical Rosewood Lodge with Sea View

"LODGE ROSEWOOD": In the heart of a tropical garden with views of the Caribbean Sea and the mountain. Charming 🤩accommodation for 2 people.🥰 1 double bedroom (bed 160x200 or 2 beds 80x200) , shower room, toilet, kitchen, dining area, deck with sun loungers. A planter and welcome accras 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 favorite

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

4.96 out of 5 average rating, 140 reviews

Mini Villa T1 Private Pool Sea View and Sea Access.

Turtle Bay Rentals Grande-Anse – Martinique Elevated studio mini villa with panoramic views of the sea and countryside. Sea access is a 50 m walk away. Beach known for its many green turtles visible in snorkel mask all year round. Composed of an air-conditioned bedroom, a shower room with toilet, an equipped kitchen on the covered terrace and a private 2 m*3 m pool on the uncovered terrace. TiSable restaurant 50 m away and small shops 500 m away.

Guest favorite

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, 268 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 favorite

An open-air bathroom features wooden walls and flooring, complemented by natural stone accents. A rainfall showerhead is situated against a wood panel, with towels hung on a bamboo ladder. Baskets are neatly arranged on a rustic table, enhancing the organic design.

Bungalow in Saint-François

4.98 out of 5 average rating, 100 reviews

Blue Palm Residence - "Le Pavillon" - St François

Welcome to the PAVILION! We look forward to welcoming you to this recent and stylish 80m2 home with its private pool. Nestled in a quiet area of St François, it is located less than 5 minutes from the town center (shops, marina, golf, airfield, beaches...) The property benefits from a relaxing setting and natural ventilation. Ideal for a relaxing holiday.