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Vacation rentals in Leeward Islands

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Top-rated vacation rentals in Leeward Islands

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Top guest favorite
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
4.98 out of 5 average rating, 130 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.

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
4.96 out of 5 average rating, 113 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.

Top guest favorite
The image captures a stunning aerial view of the estate nestled atop dramatic red rock cliffs, surrounded by lush greenery. The turquoise waters of the Atlantic Ocean crash against the rocky shoreline, showcasing the estate's secluded location on Dominica's northeast coast.
Home in Wesley
5 out of 5 average rating, 16 reviews

Eden's Gate Red Rocks Estate-AC-Laundry-Kitchen

Eden’s Gate Red Rocks Estate is a luxurious retreat on Dominica’s northeast coast perched on dramatic cliffs overlooking the Atlantic Ocean. This private estate includes Eden’s Gate Villa, a beautifully designed Villa with 1bed/1.5bath and stunning architecture, and Cottage on the Rocks, a charming 1bed/1bath apartment with magnificent ocean views. Enjoy luxurious furnishings, modern comforts, and breathtaking coastal scenery. Perfect for relaxation or adventure; it’s your own slice of paradise!

Guest favorite
A serene pool area invites relaxation, featuring a clear blue water surface reflecting the sky above. Modern outdoor seating is arranged beside the pool, with lush greenery framing the space, enhancing the calming atmosphere of the terrace.
Apartment in St. George
4.92 out of 5 average rating, 50 reviews

Natural Mystic

Breathtaking Views, Private Pool, and Elegance Await Featuring a terrace for alfresco dining beside bar, grill, pool and lush landscaping. Discover an inviting living room adorned with modern artwork, two bedrooms with ensuite bathrooms and walk-in closets, and a fully equipped kitchen with wine cooler and coffee maker. Stay active in our gym with a treadmill, workout bench, and weights. Just 20 minutes from the airport, 5 minutes drive to supermarket, the restaurant strip and the beach.

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, 212 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
Villa in Soufriere
4.93 out of 5 average rating, 427 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

Guest favorite
A shaded balcony area is furnished with comfortable seating and a central coffee table. Lush greenery surrounds the space, while expansive ocean views are visible through the railing. Light curtains gently sway in the breeze, enhancing the serene outdoor atmosphere.
Cottage in Toucari Bay
4.92 out of 5 average rating, 101 reviews

Coconut Cottage - Stunning Oceanview

Coconut Cottage was built in 2013 by local craftsmen from the village of Toucari. The structure is all timber with tiled floors and many windows for natural lighting. Stunning ocean views await you! There is a short walk downhill to a lovely beach, local restaurant and a quaint fishing village. Snorkeling, kayaking and swimming are just a few of the activities that await you! Located 10 minutes from Portsmouth where there is shopping and amenities @coconutcottagedominica

Top 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, 188 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 cozy seating area features a comfortable sofa adorned with decorative pillows, overlooking a wooden deck surrounded by lush greenery. Tables and chairs are visible, softly illuminated by string lights. Scenic views of trees and distant landscapes enhance the tranquil atmosphere.
Treehouse in Gros Islet
4.98 out of 5 average rating, 87 reviews

Seaview Sanctuary: Glamping Retreat Saint Lucia

Indulge in the romantic ambiance of this Canopy Hideaway, a unique retreat where rustic charm meets modern comfort. Enjoy breathtaking views of the Caribbean Sea and neighbouring island . Immerse yourself in the tranquility of swaying trees and the melody of crashing waves .Let the symphony of nature from the gentle rustle of leaves to the chorus of birdsong, lull you into tranquility ! Come and experience an unforgettable retreat in our KaiZen TreeHouse .

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, 265 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 😉

Guest favorite
A private plunge pool is framed by natural stone walls and vibrant tropical plants. The clear blue water reflects the surrounding greenery, while steps lead into the pool. A splash of red from a nearby flower adds a touch of color to the peaceful setting.
Villa in Saint Andrew Parish
4.88 out of 5 average rating, 32 reviews

Escape Villa with private pool

This stunning private luxury villa is nestled in an exotic jungle setting. The villa is located on Calibishie beach next to the Red Rocks & Chocolate Factory. Each king bedroom opens to a private plunge pool from their ensuite bedrooms. The bedrooms are with Air conditioning. The private pool with an over sized covered outdoor patio gives view on the beautiful Caribbean ocean. The villa has an equipped kitchen, a living room with TV and wifi.

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, 174 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 .

Popular amenities for Leeward Islands vacation rentals