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Holiday rentals in Leeward Islands

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Top-rated holiday rentals in Leeward Islands

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

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Guest favourite
A serene outdoor space features two lounge chairs positioned near an infinity pool. The pool overlooks a scenic view of Castries Bay, framed by lush greenery and colorful flowers, under a sky scattered with clouds.
Flat in Charlotte
4.86 out of 5 average rating, 239 reviews

Ocean Crest Villas

Beautiful Villa overlooking the picturesque Castries Bay, featuring convenient on-site vehicle rental and infinity pool. It is within walking distance to the Sandals La Toc Beach and a short drive to popular restaurants, bars and duty-free shopping. This villa offers guests the utmost in modern Caribbean luxury and comfort with very spacious living spaces. Balconies are prefect for outdoor lounging and dining where guests can enjoy the fresh sea breeze and stunning views of the Caribbean Sea.

Guest favourite
An inviting wooden deck features a private pool with clear water, overlooking the expansive Caribbean Sea. Lounge chairs are arranged nearby, adorned with decorative pillows. Lush greenery surrounds the area, enhancing the view of the distant mountains and coastline.
Villa in Vieux Fort
4.89 out of 5 average rating, 159 reviews

Villa Pierre: A Luxury Hidden Gem in Saint Lucia

"EXPECT TO BE ABSOLUTELY BLOWN AWAY..." Tiffany, Tennessee, USA FREE Airport Pick-up and a complimentary freshly prepared home-cooked meal upon arrival on all bookings! In addition: Stay 7 nights and “Experience the Exceptional” with a one FREE dining experience with a 5 star Private chef. Enjoy an exquisite 4 course meal carefully crafted and served in the privacy of the villa. Celebrate your special moments in a truly unforgettable way! All the amenities of a resort in a private villa!

Top guest favourite
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.
Flat in Deshaies
4.97 out of 5 average rating, 119 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.

Superhost
Villa in Sapphire
4.94 out of 5 average rating, 125 reviews

VillaAura 15-25mins from UVF Airport & Attractions

Aura Villa sits majestically on a cliff overlooking a beautiful naturally flowing river. Waking up to the melodious chirping of birds is the highlight of every morning ! On evenings, lounge out on the pool deck and enjoy a magical night sky. Whether you choose to enjoy a refreshing swim in the crystal clear infinity pool or enjoy a warm bath under the rain shower, tranquility awaits you. The lush vegetation forest views which greets this villa from the valley top will leave you in complete awe!

Top guest favourite
Villa in Woodford Hill
5 out of 5 average rating, 35 reviews

Turtle Beach villa, Private beach

Conveniently located 10 minutes from the airport, escape to a private beachfront villa offering modern luxury, ocean views, and total tranquility—walk onto the sand from your doorstep. Enjoy freshly prepared meal by a chef or choose to cook your own. Perfect for families seeking comfort, friends spending quality time together or couples looking for romance and peace. Relax by your pool or one of the island's most beautiful beaches. Experience a warm hospitality designed for rest and connection.

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
4.9 out of 5 average rating, 194 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
4.87 out of 5 average rating, 216 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 favourite
Home
4.94 out of 5 average rating, 111 reviews

Gîte Kolin's view

KOLIN’S view, moderne et contemporain, est situé sur une propriété sécurisé privée avec parking. Il est entièrement équipé et ouvert sur l’extérieur avec mini piscine privative. Le site est également muni de citernes vous permettant de ne pas manquer d’eau. La ZAC à proximité vous donnera accès à toutes commodités. La situation géographique permet de profiter d’une vue montagne, d’accéder aux nombreuses cascades, randonnés, plages, spots de plongée, brasserie local, marché…

Guest favourite
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, 104 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

Guest favourite
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
4.96 out of 5 average rating, 198 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.

Guest favourite
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, 34 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 favourite
An outdoor dining area features a table set for four, complemented by modern chairs. A small private pool is visible nearby, framed by wooden decking. Light colors on the walls and lush greenery enhance the inviting setting, with large sliding doors leading to the interior.
Home in Flamands
4.95 out of 5 average rating, 180 reviews

Etoile du Nord

ETOILE DU NORD is located opposite Flemish Beach, from which you can enjoy the exceptional views from every corner of the villa modern, functional, it is ideal for a couple or family with big children who will appreciate the independence of the second bedroom located on the lower level. Just cross the road to get to the beach, whether it's a morning bath in the rising sun, a day of laziness, or an evening stroll along the bay.

Popular amenities for Leeward Islands holiday rentals