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Holiday houses in Leeward Islands

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Top-rated holiday rentals in Leeward Islands

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Top Guest favourite
A wooden walkway leads towards a bright bungalow, framed by a lush green landscape. Tropical plants and colorful flowers adorn the pathway, while the distant ocean can be seen under a clear blue sky. Sunlight illuminates the vibrant surroundings.
Bungalow in Deshaies
4.95 out of 5 average rating, 105 reviews

"Carambole" Bungalow vue mer piscine privative

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

Top Guest favourite
A serene outdoor space features a modern freestanding bathtub overlooking the ocean. A stylish hanging chair is positioned nearby, surrounded by potted plants. Natural light illuminates the deck, enhancing the views of the landscape and sea beyond.
Tiny home in Willoughby Bay
4.97 out of 5 average rating, 114 reviews

Cozy Stargazer Pod - Ocean View/No Cleaning Fee

Escape the ordinary vacation; immerse yourself in nature and reconnect with your body's natural rhythm. At Coastal Escape Antigua's stargazer pod, experience vacationing at its romantic, luxurious best overlooking breathtaking Willoughby Bay. This unique getaway is perfect to recharge from the stresses of life or to reconnect with that special someone. There are no alarm clocks here; natures orchestra of birds, crickets and grasshoppers will lull you to sleep and welcome you into the new day.

Guest favourite
The open living area features a comfortable seating arrangement with plush cushions, accompanied by a decorative coffee table adorned with tropical flowers. The kitchen, visible in the background, is bright and equipped with basic cooking utensils. Large windows allow for natural light and scenic views of the surrounding greenery.
Cottage in Falmouth
4.94 out of 5 average rating, 136 reviews

Cleopatra - English Harbour

Cleopatra is a large, open, one-bedroom cottage with comfortable lounge, King bed, and kitchen on Pineapple House property in English Harbour. Our favorite amongst several cottages, everything is in white; everything is open, & the kitchen is big. Stunning view of Super Yachts in Falmouth Harbour. Gated Community. Wi-fi. Night life. Restaurants. Spas. Activities. Steps from Nelson's Dockyard. Steps from Pigeon Beach, where there are two beach bars. Houseskeeping Services. Open October to May.

Top Guest favourite
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 in LC
4.96 out of 5 average rating, 181 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 favourite
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, 161 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
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
4.95 out of 5 average rating, 151 reviews

Appartement DEEP BLUE vue mer - piscine privative

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.

Superhost
An indoor living space features a wooden table surrounded by cushioned seating. Light filters through handmade glass bricks, creating colorful patterns. An arched doorway leads to a kitchen area, while large windows provide views of the lush garden outside.
Cottage in Soufriere
4.9 out of 5 average rating, 106 reviews

Lower Love. Ecolodge in tropical garden, Dominica

Prepare for a truly magical holiday in Dominica. 100% off grid, solar powered, gravity rain fed, yet with satellite internet, this architect designed ecolodge invites you to relax and rejuvenate. The stunning inside-outside living room is the perfect place to watch the hummingbirds as you sip a fresh coffee. Surrounded by a lush tropical garden, yet within walking distance of Soufriere and the Caribbean sea. Get away from it all in this breathtaking setting, the Nature Island at its best.

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, 203 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 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, 168 reviews

Tuwana

Tiny House perché sur une colline à 400m d’altitude au milieu d’un jardin fruitier. accessible par un chemin forestier en bon état. Lieu calme et isolé entre mer et montagne avec une vue dominante. Logement naturellement frais et aéré sans moustiques. Logement écologique . Situé à 10 min de la plage de Leroux à 20 min de la plage de Malendure à 20 min de la plage de Grande Anse Adaptée aux personnes qui souhaitent se déconnecter, se reposer ou se ressourcer.

Top Guest favourite
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, 254 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 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, 258 reviews

Lodge Rosewood atypique avec vue mer

"LODGE ROSEWOOD" : Au coeur d'un jardin tropical avec vue sur la mer des caraïbes et la montagne. 🤩Logement de charme pour 2 personnes.🥰 1 chambre double (lit 160x200 ou 2 lits 80x200) , salle d'eau, wc, cuisine, coin repas, deck avec chaises longues. Un planteur et accras de bienvenue vous sont offerts Masques, tubas, palmes à disposition, si besoin. Boite à livres. Le lodge Rosewood n'est plus disponible sur vos dates, vous pouvez consulter l'annonce du "COUNTRY LODGE" 😉

Guest favourite
A spacious sitting area features large windows that offer views of the surrounding forest and distant mountains. Louvered windows allow for gentle breezes. The room includes two wicker chairs, a coffee table, and bright blue upholstery on a sofa.
Cottage in Calibishie
4.88 out of 5 average rating, 128 reviews

The Cottage at Villa PassiFlora

The Cottage at Villa PassiFlora represents an excellent choice for individuals or couples who don’t need the space of the Villa, and it adds the option of stays of fewer than 4 nights. The cottage is on the Villa PassiFlora property, surrounded by forest, fruit trees and tropical plants, with a view through the forest to the Atlantic Ocean. Guests have ready access to the trail leading to Pointe Baptiste.

Popular amenities for Leeward Islands holiday rentals