Vacation rentals in Leeward Islands

5 out of 5 average rating, 113 reviews

A vast expanse of turquoise water extends to the horizon, with gentle waves creating patterns on the surface. Nearby islands are visible in the distance, under a clear blue sky dotted with soft white clouds.

Villa in Christiansted

Mojito Hill - private hilltop pool oasis!

Beautiful 1-bedroom ocean view villa with private pool. Relax on the private pool deck with brand new patio furniture featuring chaise lounges, table seating for 4, and a gas grill. Sweet dreams await you in the four-poster king sized master suite, complete with french doors that open to the pool deck and allow for the ocean breezes to keep you cool. The shower is a fully stocked oversized marble shower with room for two. A fully equipped kitchen with granite countertops and modern appliances, including a Keurig latte machine, will make you feel right at home. Mojito Hill includes many conveniences such as a smart TV, wifi, air conditioning, washer/dryer, and much more. Extra guests are no problem, as the couch features a pull-out bed. Villa Madeleine is a gated community on St. Croix’s relaxing East End, where you will enjoy the privacy, amazing views, tennis court, and close proximity to the Reef Golf Course, Duggan’s Reef restaurant, Divi Casino and Resort, Grapetree beach to the south and Reef Beach to the north. All these amenities are within walking distance, but do require traversing a steep hill, so driving is typically preferred. We have an on-island manager, and Tom & Hillery are available at any time via email/text/phone if needed. If you don't see the dates you are looking for, please message us, we also have a Splash of Lime in the same complex that has a spectacular northern facing view.

4.95 out of 5 average rating, 171 reviews

An outdoor deck area is framed by lush greenery and vibrant pink flowers, offering views of the tranquil Caribbean Sea. A cozy seating area with pink loungers invites relaxation under the protective overhang of the structure's roof.

Guesthouse in LC

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.

4.96 out of 5 average rating, 28 reviews

A serene infinity pool is positioned on a wooden deck, overlooking the calm Caribbean Sea. Lush greenery borders the pool area, while two lounge chairs invite relaxation in the sunlight. The scene is enhanced by blue skies and the presence of palm trees swaying gently in the breeze.

Tent in Castries

A Luxury Tented Experience - Waterfront

Immerse yourself in a lush acre of private waterfront property offering: - saltwater infinity pool - romantic safari tent - private sand beach - snorkelling - private central location - unique active views - magical sunsets - outdoor kitchen/bar - coral stone shower - orchard - hammocks - car/boat tours - in-house professional massage - couples masterclass Lumière is one of a kind in St. Lucia, offering a waterfront, luxury ‘glamping’ experience like no other. Enjoy peace and adventure here.

4.91 out of 5 average rating, 172 reviews

A uniquely designed bathroom features a glass vessel sink set on a wooden countertop. A fish-shaped mirror adds a whimsical touch, while the walls combine wood and corrugated metal, creating a rustic aesthetic. Compact storage is visible, accentuating the clever use of space.

Villa in LC

Treehouse Hideaway Villa I - Piton & Ocean Views

Welcome to our Superhost owned, fully updated, Piton and ocean view villa near the Jade Mountain Resort and Anse Chastanet beach, known for its excellent diving and snorkeling. This cozy, romantic, and natural tree house-inspired villa is designed to take in the amazing Pitons and lush tropical environment. Our popular standalone one bedroom, one bath villa with great kitchen features a very welcoming staff, refreshing private salt plunge pool, and lush tropical gardens is certain to delight.

4.9 out of 5 average rating, 168 reviews

A serene corner of the villa is framed by lush greenery, showcasing the infinity pool adjacent to the expansive terrace. Large glass doors allow natural light to fill the living area, highlighting the seamless interplay between indoor and outdoor spaces.

Villa in Soufriere

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.

4.87 out of 5 average rating, 187 reviews

An aerial view showcases a sprawling villa nestled within lush greenery. Surrounding palm trees and tropical foliage frame the outdoor pool area, highlighting the villa's unique architecture and harmonious integration into the landscape.

Villa in Soufriere

Villa Piton Caribbean Castle

Certified to host on St Lucia government website at stlucia.org. 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 fee prepaid through Airbnb prior to your arrival. 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!

4.98 out of 5 average rating, 176 reviews

A spacious wooden deck features a spa surrounded by tropical greenery, with a view of the lush mountain in the background. Sunlight gently highlights the slopes, and a potted plant adds a natural touch to the outdoor space.

Villa in Le Morne-Vert

Creole wooden cottage with jacuzzi – Le TiLokal

TiLokal gîte is located at the foot of the Pitons du Nord, a UNESCO World Heritage Site. Access to the Coco River through the 3000 m2 garden planted with local trees and flowers. You're in the rainforest. Here, no need for air conditioning, the wooden construction, the blinds integrated into the windows and the place make it a naturally ventilated home. This is the ideal place to enjoy eco-friendly tourist activities: hiking, canyoning, sailing trips, diving, massages...

4.97 out of 5 average rating, 127 reviews

A wooden deck is shown, featuring two rustic chairs positioned around a unique tree stump table. A lush green landscape surrounds the area, with trees providing a natural backdrop and a glimpse of the ocean visible in the distance.

Tiny home in Deshaies

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.

4.96 out of 5 average rating, 148 reviews

An outdoor dining area features a wooden table set for four, with plates and cutlery arranged neatly. A view of the coastline, ocean, and distant hills can be seen in the background. The space is complemented by a small jacuzzi and a stroller placed nearby.

Home in Saint-Barthélemy

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 .

Villa in Saint Barthélemy

A spacious living area features a comfortable gray sofa and a wooden coffee table, complemented by a large flat-screen television mounted on a light wood media console. Expansive glass doors offer stunning views of the sea and allow natural light to fill the room.

4.97 out of 5 average rating, 148 reviews

Villa RIDE

RIDE is a 2017 VILLA located on hilltop of anse des cayes offering a beautiful seaview. 5 min driving from the beach , gustavia ( main city ) , and a delicious bakery store. It offers quiet and privacy while remaining close to everything. The villa can welcome 4 PEOPLE in 2 BEDROOMS, each one having their own private massive wood bathroom . The villa is also accessible to people with REDUCED MOBILITY thanks to its one level access.

Cottage in Portsmouth, Saint John Parish, DM

The upper level studio showcases a spacious wooden countertop with seating for four, providing an inviting cooking and dining area. Light streams through the open-air lounge, illuminating the natural wood beams overhead. The backdrop features greenery, enhancing the connection to nature.

4.96 out of 5 average rating, 257 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

4.98 out of 5 average rating, 122 reviews

Bungalow in Deshaies

Du Côté De Chez Swann – Racoon Bungalow –

Here you will be at home. Welcome to your little slice of heaven nestled in the heart of the beautiful rainforest of our property. With its stilt terrace, this brand new bungalow offers exceptional views of Grande Anse Bay. Located below our house, a small intimate set of 3 bungalows awaits you in peace, each bungalow is isolated in its small bubble of greenery where you can fully enjoy your private jacuzzi.

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Popular amenities for Leeward Islands vacation rentals

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Other great vacation rentals in Leeward Islands

5 out of 5 average rating, 8 reviews

An inviting infinity pool is set on a wooden deck, offering unobstructed views of the ocean and a small island in the distance. Two lounge chairs are positioned on the deck, allowing for relaxation while enjoying the serene coastal landscape.

Villa in Bouillante

Villa with panoramic sea view

JeanRating, 5 stars3 months ago

What a pleasure! We were captivated by the view... During the day, a splendid view - sailboats, the reserve, the reliefs and the blue sea as far as the eye can see - at night, stars endlessly... The accommodation is neat, everything is beautiful and harmonious, a sought-after design... A large, beautiful and so pleasant pool (and what a view;)) A few days after my booking, a small photo received to show me the good weather and make us want... very nice! Really clear and complete explanatory videos... No complaints... In view of this exceptional property and the work done by the owners, we paid attention to it, but what a job! We were won over, we would have stayed longer... Just specify no sunscreen in the pool, but with children's UV t-shirt; Ras. In short, a real pleasure in a real beautiful house! Thank you PS: we are bragged about the turtles of Malendure; it's not a legend! What a joy!

4.95 out of 5 average rating, 21 reviews

An infinity pool glistens under a clear blue sky, surrounded by a spacious sun deck equipped with lounge chairs. Lush greenery and a scenic view of the landscape enhance the outdoor space, complemented by stone walls and wooden railings.

Apartment in St. George

Quiet Charm

JudelleRating, 5 stars3 months ago

Words are not enough to explain how amazing this place was. This is by far the best airbnb I’ve stayed at and by far the best host I have interacted with. Ellsworth was polite, friendly, proactive, insightful and prompt. All of his recommendations are on point and he does his best to curate a great experience based on what it is you are looking to do. The house was spotless and accurate to the T of descriptions listed. I fell in love with every inch of the property especially the pool. Looking forward to having another opportunity to book Ellsworth’s home in the near future.

4.88 out of 5 average rating, 93 reviews

A charming ecolodge is nestled amidst lush tropical vegetation, featuring vibrant foliage and colorful flowers in the foreground. The building blends harmoniously with its surroundings, showcasing unique architectural details and a welcoming entrance. Tall trees and greenery create a serene and private atmosphere.

Cottage in Soufriere

Lower Love. Ecolodge in tropical garden, Dominica

RebeccaRating, 5 stars3 weeks ago

The stay was fantastic. The whole cottage has his own charm and gives you peace and Harmony. You can see that the house was built with love and designed to be ecologically. Love it! Nell is super kind and proactive in her communication. All the tips were super helpful. No Wi-Fi also gives you the opportunity to detox for a while, try it! I visited Dominica outside the season. Some tips in general would be to buy grocery, nevertheless if you plan to eat outside. Outside the season, there are not many restaurants open, especially not in the village. Renting a car is a must. Planned to book none, but then changed mind after talking to couple of people ☺️ It just helps you to move around and to explore the island the fullest! I would always recommend to book Nells Cottage of Coming to Dominica! 🌸 Thank you for the hospitality!

4.96 out of 5 average rating, 164 reviews

Treehouse in Laborie

Bay Treehouse

GrahamRating, 5 stars1 month ago

Our stay at The Treehouse, hosted by Tony and Jan, was absolutely fantastic! It's an amazing building in an incredible location, surrounded by abundant wildlife and just a stone's throw from the beach. Tony and Jan were truly excellent hosts – so friendly and hospitable. They communicated brilliantly, made us feel incredibly welcome, and provided a plethora of invaluable advice and tips on where to eat, visit, and what to do. You definitely won't be disappointed after a visit here!

4.99 out of 5 average rating, 103 reviews

A private terrace is equipped with two lounge chairs and a small table, surrounded by lush greenery. The view showcases clear blue waters and gentle hills in the distance, creating a serene coastal atmosphere.

Apartment in BL

Appartement Gemma

DeannaRating, 5 stars2 weeks ago

Fanelie was an amazing host! Had a list of local recommendations that we thoroughly enjoyed, always available with a quick response if we had any questions. The apartment was so nice, well stocked kitchen, great air conditioning, beautiful patio views of the beach. Hope to be back soon!

4.97 out of 5 average rating, 63 reviews

Townhouse in Le Gosier

Villa Bord de Mer Apartment – Private Dock

LoïcRating, 5 stars1 month ago

A big thank you to the hosts for their warm hosting and availability, even ready to brave the storm in the literal sense to welcome us! The house is beautiful, very well thought out, with a soothing atmosphere. The bedding is comfortable, the view from the rooms is superb, and waking up facing the sea and the pool will remain a very good memory. I particularly enjoyed having breakfast on the pontoon, in the calm of the morning. The location is also ideal, within walking distance of many restaurants. A relaxing and pleasant break. Thanks again!

4.85 out of 5 average rating, 53 reviews

A spacious wooden deck hosts a jacuzzi surrounded by lush greenery. Two lounge chairs are positioned nearby, providing a relaxing space amidst nature. The setting offers a serene atmosphere, inviting guests to unwind after a day of exploration.

Cabin in Goyave

Bungalow among the trees

StéphanieRating, 5 stars4 weeks ago

Met our expectations for our wedding anniversary. A unique place in the heart of nature with a jacuzzi as a bonus for the end of the evenings. Our host is attentive, that's the least we can say. You can book without a second thought.