Vacation rentals in Leeward Islands

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Top-rated vacation rentals in Leeward Islands

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Top guest favorite

A private pool deck features a refreshing blue pool surrounded by lush greenery. New patio furniture includes two chaise lounges and a table for four, complemented by a gas grill. Views of the ocean create a peaceful outdoor atmosphere under a clear blue sky.

Villa in Christiansted

5 out of 5 average rating, 117 reviews

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.

Top guest favorite

A spacious wooden deck offers a hot tub with a scenic view, bathed in warm sunlight during sunset. Surrounding lush greenery and a tropical atmosphere enhance the inviting setting of the villa.

Villa in Le Morne-Vert

4.98 out of 5 average rating, 181 reviews

Gîte créole en bois avec jacuzzi - Le TiLokal

Le gite TiLokal est situé au pied des Pitons du Nord, patrimoine mondial de l'UNESCO. Accès à la rivière Coco par le jardin de 3000m2 planté d'arbres et de fleurs locales. Vous êtes en pleine forêt tropicale. Ici, pas besoin de climatisation, la construction en bois, les jalousies intégrées aux fenêtres et le lieu en font un logement aéré naturellement. C'est l'endroit idéal pour profiter d'activités touristiques éco-responsables : randonnées, canyonning, sorties à la voile, plongée, massages...

Top guest favorite

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, 249 reviews

Lodge Rosewood

Au coeur d'un jardin tropical avec vue sur la mer des caraïbes et la montagne. 🤩Logement de charme pour 2 personnes.🥰 1 chambre double (lit 160x200 ou 2 lits 80x200) , salle d'eau, wc, cuisine, coin repas, deck avec chaises longues. Un planteur et accras de bienvenue vous sont offerts Masques, tubas, palmes vous sont mis à disposition si vous le souhaitez. Boite à livres dans le jardin. Le lodge Rosewood n'est plus disponible sur vos dates, vous pouvez consulter l'annonce du "Country Lodge" 😉

Guest favorite

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, 160 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.

Top guest favorite

A landscaped outdoor area features vibrant flowers and palm trees framing a traditional Japanese gazebo. The path leads down to a picturesque view of the ocean and surrounding islands under a partly cloudy sky, illuminated by soft sunlight.

Apartment in Christiansted

5 out of 5 average rating, 150 reviews

Frigates View

This secluded mountainside oasis, conveniently located mid-island, provides panoramic views of Salt River Bay, Buck Island and surrounding islands. A spacious studio with private veranda and separate entry off a verdant courtyard adorned with exotic flora, offers a stunning 180 degree ocean seascape. Enjoy beautifully landscaped grounds, Japanese gazebo and jacuzzi, while listening to the sounds of the breaking surf and cooled by constant trade winds. A perfect blend of romance and relaxation .

Guest favorite

A private pool is featured on a spacious terrace, with surrounding wooden accents. The calm blue water reflects the sky, providing a serene view of the Caribbean Sea and coastal scenery. Natural light illuminates the area, enhancing the tranquil atmosphere.

Tiny home in Le Gosier

4.96 out of 5 average rating, 138 reviews

Appartement DEEP BLUE vue mer - piscine privative

The DEEP BLUE apartment is located in the heart of the village of Le Gosier in a small residence of 10 independent accommodations organized in terraces. It offers an exceptional sea view over the islet of Gosier, Les Saintes, Marie Galante and the coasts of Basse Terre. You will enjoy its furnished terrace with a private swimming pool of 2m x 5m. The apartment has been renovated and we have put our soul into this project so that you can live the Caribbean experience. FREE PARKING. Free WIFI.

Top guest favorite

A private patio is visible with two colorful Adirondack chairs, one yellow and one orange, positioned towards a stunning view of the water. Lush greenery surrounds the area, and boats can be seen floating in the serene bay under a bright blue sky.

Apartment in Ratho Mill

4.98 out of 5 average rating, 181 reviews

Coconut Lookout | Stunning views and steps to sea

Coconut Lookout nestles amongst the coconut palms with breathtaking views of both the Atlantic Ocean and Caribbean sea. Just below the apartment there are 80 steps that give access to safe swimming in Blue Lagoon. This stylish, air conditioned studio apartment consisting of a bedroom, with double bed, bathroom and kitchenette. The large private patio, with sun and shade, is a great place to relax Please note bookings for infants or children are not allowed due to the cliffside location.

Guest favorite

A wooden terrace features three lounge chairs with bright orange towels, overlooking a sandy beach and shimmering blue ocean. Lush greenery surrounds the area, while a bright sky adds to the inviting atmosphere.

Home in Saint-Barthélemy

4.95 out of 5 average rating, 155 reviews

Etoile du Nord

ETOILE DU NORD est située face à la plage de Flamand , dont vous pourrez profiter de la vue exceptionnelle depuis chaque recoin de la villa moderne, fonctionnelle, elle est idéale pour un couple ou une famille avec de grands enfants qui apprécieront l'indépendance de la seconde chambre située au niveau inférieur. Il suffit de traverser la route pour accéder à la plage, que ce soit pour un bain matinal au soleil levant, une journée de farniente, ou une ballade du soir le long de la baie .

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

4.89 out of 5 average rating, 171 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.

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 in Soufriere

4.87 out of 5 average rating, 189 reviews

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!

Guest favorite

A private terrace with wooden decking features a small pool, offering views of the bay and surrounding hills. A table and chairs are positioned nearby, creating a serene outdoor space. Bright blue skies and calm waters enhance the relaxing atmosphere.

Cottage in Les Anses-d'Arlet

4.96 out of 5 average rating, 136 reviews

Mini Villa T1 Piscine Privée Vue Mer et Accès Mer.

Turtle Bay Locations Grande Anse - Martinique Mini Villa T1 en hauteur offrant une vue panoramique sur la mer et la campagne. Accès mer à 50m à pieds. Plage connue pour ses nombreuses tortues vertes visibles en palme masque tubas toute l’année. Composée d’une chambre climatisée, une salle de douche avec WC, une cuisine équipée sur la terrasse couverte et une piscine privée de 2m*3m sur la terrasse découverte. Restaurant TiSable à 50m et petits commerces à 500m.

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, Saint John Parish, DM

4.97 out of 5 average rating, 263 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