Vacation rentals in Leeward Islands

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Top-rated vacation rentals in Leeward Islands

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A person enjoys the serene view from the edge of a plunge pool, overlooking the mountains and the Caribbean Sea. The surrounding lush greenery and the dramatic outline of the Pitons enhance the natural beauty of the setting under a clear blue sky.

Guesthouse

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.

FamilyLocationGetting around

4.96 out of 5 average rating, 193 reviews

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

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.

LocationFamilyBeach

4.89 out of 5 average rating, 205 reviews

Superhost

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

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!

LocationValueCheckout

4.86 out of 5 average rating, 223 reviews

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

Location Open Sky

110 m² accommodation with magnificent views of the Caribbean Sea and Montserrat Island. The accommodation at the bottom of a villa is entirely private and has 3 bedrooms, 2 of which have access to a large bathroom. The third bedroom is equipped with a private bathroom with a massage bathtub. All bedrooms come equipped with large king size beds, 65" smart TV, fiber Internet. Living room with kitchen open to the terrace. End-of-stay cleaning and daily cleaning included in the price.

LocationValueLaundry

4.97 out of 5 average rating, 131 reviews

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

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

LocationFamilyTV

4.93 out of 5 average rating, 107 reviews

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

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.

ValueLocationAccess

4.96 out of 5 average rating, 212 reviews

Top guest favorite

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

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

LocationValueBeach

4.97 out of 5 average rating, 312 reviews

Guest favorite

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

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.

FamilyLocationComfort

4.96 out of 5 average rating, 155 reviews

Top guest favorite

A spacious terrace features a relaxing catamaran net, inviting rest with panoramic views of the sea and surrounding landscape. A potted plant adds a touch of greenery. Comfortable seating is provided by a nearby chair, enhancing the outdoor experience.

Home in Vieux-Habitants

Panorama Kréyòl : Bungalow

Discover Panorama Kréyòl, a bungalow on stilts with spectacular sea and mountain views. In the heart of Basse-Terre, enjoy a warm wooden setting, a private jacuzzi and total immersion in Guadeloupean nature. Enjoy the proximity of idyllic beaches, hikes to La Soufrière, and waterfalls. Air-conditioned and equipped with a terrace with catamaran net, it offers comfort and adventure. A travel guide is included.

LocationBeachBathroom

4.98 out of 5 average rating, 104 reviews

Guest favorite

Villa in Saint John's

Villa Surr Coline

NEWLY RENOVATED. POOL AND A/C NOW INCLUDED! Villa Surr Coline is a unique luxury villa nestled on the hilltop of McGuire Park. This private lush villa boast 180 degree views of the rolling hills of Buckleys. Relax in the infinity pool or enjoy a cocktail on the outdoor floating bed. The entire property is yours to enjoy! Villa Surr Coline is only a 20 minute drive away from over 5 beaches!

ValueLocationIndoor spaces

4.86 out of 5 average rating, 182 reviews

Guest favorite

Apartment in Basse-Terre

Les Terrasses du Fort Vue mer et couchers soleil

Les Terrasses du Fort offers elegant and comfortable accommodation, ideally located in close proximity to Fort Delgrès. Designed for couples, business stays or relaxing getaways, it provides a modern, calm and well-kept setting with a warm and intimate atmosphere. Strategic location, premium comfort and complete independence for an uncompromising stay in Guadeloupe.

LocationRiverAmenities

4.91 out of 5 average rating, 66 reviews

Top guest favorite

A sunlit deck features comfortable loungers with a straw hat resting on one. Lush greenery surrounds the space, while the iconic Pitons rise majestically in the background against a vibrant blue sky and tranquil sea.

Villa

La Batterie Villa • Boutique Villa • Amazing Views

Tucked away in the prestigious Anse Chastanet / Jade Mountain area of Soufrière, the Villa is a private retreat designed for relaxation, comfort, and unforgettable views. Perched 300 feet above the Caribbean Sea and facing the iconic Pitons, the villa enjoys cooling island breezes and panoramic scenery that never fails to impress.

LocationFamilyCheckout

4.97 out of 5 average rating, 157 reviews