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Holiday rentals 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, 106 reviews

"Carambole" Bungalow with sea view and private pool

Welcome to Carambole et Ananas, your little piece of paradise nestled in the heart of the banana plantations. This intimate set of 2 brand new bungalows offers a magnificent view of the breathtaking bay of Grande Anse. Ideally located on a private property, a 5-minute walk from the beach, on the first heights of Deshaies, they will guarantee you a change of scenery, privacy, calm and tranquility. Come and admire the beautiful sunsets from your private pool while enjoying a tasty Planteur cocktail

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, 119 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, 164 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
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, 107 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.

Top 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
4.97 out of 5 average rating, 175 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 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, 260 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 😉

Top 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, 154 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, handmade with coconut oil and no fragrance Salt, pepper Instant coffee 1 towel each Cafetiere

Superhost
A vibrant landscape features lush tropical foliage, including palm trees and blooming bougainvillea. A glimpse of the harbor reveals numerous boats, surrounded by charming buildings and lush hills, with the sea in the background. The scene conveys a relaxed, coastal atmosphere.
Apartment in BL
4.96 out of 5 average rating, 103 reviews

Beautiful Studio Gustavia Pool View Parking

Located within the Colony Club residence in the heart of Gustavia. Le Petit Barth is the perfect base for enjoying a wonderful vacation in Saint-Barthélémy. View of the harbor, Shell Beach and city center within walking distance, you will enjoy a perfect location. Completely refurbished with luxurious materials and refined Caribbean decor. You can also enjoy a beautiful infinity pool overlooking the harbor as well as a parking space.

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, 286 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 bright and airy living space showcases a white sectional sofa, complemented by a round area rug. A wall-mounted television is visible, while a hammock hangs nearby, inviting relaxation. Natural light filters through expansive openings, connecting the interior to the outdoor wooden deck.
Villa in Anse Des Cayes
4.96 out of 5 average rating, 144 reviews

The Perfect Beach House

Villa Palmier is a stunning 2 bedroom, 2 bathroom newly renovated villa in the well located neighborhood of Anse Des Cayes. It is a designers dream having just been featured in the July/August issue of Elle Decor France. With ocean views from every room, a constant sea breeze blowing throughout, and your own private pool, it's the perfect beach retreat.

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, 138 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.

Top guest favourite
An outdoor terrace is adorned with two lounge chairs under a large umbrella, accompanied by a small dining table surrounded by woven chairs. Lush greenery provides privacy, while a small swimming pool is visible in the background.
Home in Lorient, Saint Barthélemy
5 out of 5 average rating, 132 reviews

Casa Dolorès

With your feet in the sand, less than a minute from the sea, La Casa Dolorès is the perfect place for a total change of scenery and an ideal stay. Feet in the sand, in less than one minute from the sea, Casa Dolorès is the perfect place for a wonderful stay on our beautiful island.

Popular amenities for Leeward Islands holiday rentals