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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 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, 125 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
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, 128 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
The villa is nestled on a hillside, showcasing a modern design with a grey roof and stone accents. An infinity pool reflects the surrounding greenery, while large glass doors create a seamless transition between indoor and outdoor spaces.
Villa in Soufriere
4.91 out of 5 average rating, 190 reviews

Enclave Villa V3 -Overlooking Pitons & Ocean ! Wow

Enclave Villa V3 is a 2 bedroom villa with much to offer. This elegant property sleeps 4 and boasts such amenities as a Infinity pool off of both the master bedrooms. Located in Soufriere, the quintessential attraction capital of St. Lucia, Enclave 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.

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, 210 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
Guest suite in Cades Bay
5 out of 5 average rating, 4 reviews

“FreeBird” - with panoramic volcano & ocean views

Brand New, unique & tranquil, rest with amazing 180’ panoramic east / west views of volcano & ocean. The “freebird” bedroom suite on Nevis island is born out of the chic eccentric lifestyle of its world traveled owners. Decorated with tastes of a Mediterranean chic, ultra lounge & romantic West Indian grooves ❤️ 1 bed / 1 bath with a freestanding soaking tub & candlelight romantic accents Enjoy watching the monkeys, moonrise & sunset from this truly amazing lookout retreat.

Guest favourite
A view from a shaded terrace features two lounge chairs positioned on a wooden deck, overlooking a sandy beach. The calm water reflects the blue sky and distant hills, while boats are anchored nearby. Palm trees sway gently, enhancing the tranquil coastal atmosphere.
Home in Terre de Haut - Les Saintes
4.86 out of 5 average rating, 207 reviews

In the Bay of Saints, right by the water

With your feet in the water on a white sandy beach, our house is located in Terre-de-Haut in the Saintes archipelago (Guadeloupe), nestled in the heart of its wonderful bay and in the typical fishermen's district of Fond de Curé. Close to all amenities, no need to rent a vehicle for your shopping or to go to the beach, everything is on site. The house is 90 m2 in duplex with a 30 m2 terrace overlooking the sea. Comfort, quiet and beauty will fill you with happiness.

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, 180 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, 261 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 sleek lounge chair is positioned beside an infinity pool, offering a clear view of the ocean and coastline. Lush greenery and vibrant flowers surround the area, complementing the serene blue waters under a partly cloudy sky.
Villa in Raisins Clairs
5 out of 5 average rating, 15 reviews

Topaze Beach: 4-star Villa Pool - Sea and Beach Front

Nestled in a quiet little corner, 2 totally independent villas, Rubis and Topaze, will offer you the best to help you have a great vacation. Close to amenities. Certified 4-star villas. The villas are modern, practical and tastefully furnished. The Rubis villa has trendy red furniture and the Topaze villa has trendy gray furniture. All rooms have a magnificent sea view Autonomous in case of water cuts. Villas with concierge

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, 289 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 cozy bedroom features natural wood paneling and a thatched ceiling, illuminated by soft light. A spacious bed is adorned with decorative pillows, and a bedside table crafted from wood adds to the rustic charm. A large sliding door leads to the outdoor space.
Home in Saint-François
4.96 out of 5 average rating, 109 reviews

The Secret Kabane, Pool, SPA, King Size Bed

The Secret Hut is a true bubble of love designed entirely for couples. Here, tropical nature and the exceptional comfort of a bohemian chic lodge meet to rejuvenate you in a timeless moment and create a unique and unforgettable experience. In a haven of tranquility and authenticity, the Secret Kabane is built around the swimming pool and jacuzzi, in an indoor/outdoor atmosphere that invites you to relax and unwind.

Guest favourite
An infinity pool reflects the clear blue sky, surrounded by stone walls and tropical vegetation. Comfortable outdoor seating is positioned on a terrace above the pool, offering scenic views of the lush landscape and distant horizon.
Flat in St. George
4.96 out of 5 average rating, 28 reviews

Quiet Charm

Take it easy at this unique and tranquil getaway,nestled amidst nature’s embrace. This cozy haven invites you to escape the hustle and bustle of daily life and immerse yourself in the tranquil beauty of the surroundings. Whether you’re savouring a morning coffee on the private deck or taking a refreshing dip in the infinity pool, this apartment promises a peaceful escape.

Popular amenities for Leeward Islands holiday rentals