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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 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, 113 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 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.

Top 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 in Deshaies
4.97 out of 5 average rating, 125 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
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
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, 167 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.

Guest favourite
An outdoor deck features two lounge chairs with cushions, a small table adorned with potted plants, and a pitcher beside glasses. The setting is illuminated by a warm sunset, creating a serene ambiance over the water.
Townhouse in Jolly Harbour
4.92 out of 5 average rating, 113 reviews

Waterfront Villa – Designer Tropical Getaway

Townhome with 2 bedrooms, 2.5 bathrooms, 1200 sq. feet (111 sq. meters). Water facing private deck and 2 balconies with western sunset views. Fully stocked and equipped kitchen. On-site private parking for smaller cars; parking for larger vehicles a few steps away. Gated community with restaurants, bars and cafes, golf course, marina, supermarket, banks and rental car agencies. 10-minute walk to North Beach and golf course, 20-minute walk to restaurants, shops, other amenities.

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

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 deckchairs. 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 consult the "COUNTRY LODGE" listing 😉

Top Guest favourite
The exterior of Boulder Cottage showcases a covered patio area with wooden louvers, overlooking Falmouth Harbour. Lush greenery and stone accents frame the scene, while the tranquil water and sailing boats are visible in the background under a softly lit sky.
Cottage in Cobbs Cross Hill
4.95 out of 5 average rating, 179 reviews

Private cottage stunning view!

Nestled in a woodland forest overlooking Falmouth Harbour, 10 min from Historic Nelsons Dockyard, 3 Marinas, Beach and all amenities. Boulder Cottage is very private, has a King sized bed, full kitchen, patio dining, plunge pool and stunning views! Also on property is Antilles Stillhouse, a Craft Distillery! The first of its kind in the region, David, master distiller, focuses on making high quality spirits utilising local botanicals.

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, 280 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 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
4.9 out of 5 average rating, 145 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: Vermont Trail, 'Vincy' parrot Bush Bar 10 mins. Table Rock 1 hr Drive: Superb snorkelling site 45 mins. Provided: Soap Salt, pepper Instant coffee 1 towel each Cafetiere

Top Guest favourite
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, 71 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.

Top Guest favourite
The entrance of the cottage reveals a wooden deck adorned with seating, framed by lush green foliage. A seamless connection to nature is emphasized by the surrounding rainforest, with views extending into the vibrant landscape beyond.
Cottage in Rosalie
4.99 out of 5 average rating, 135 reviews

Banana Lama Eco-Cottage

This property is part of Banana lama eco Villa and Cottages. It’s an off- grid fully sustainable accommodation in the rain forest of Dominica and situated on a pristine river. Come escape from it all. Property is accessed by foot and zip-line across the river. Bring a good pair of river shoes and a back pack.

Popular amenities for Leeward Islands holiday rentals