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, 119 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.

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 in LC

4.95 out of 5 average rating, 174 reviews

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.

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.

Guest favorite

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, 116 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

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, 140 reviews

DEEP BLUE apartment, sea view – private pool

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.

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 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!

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, 250 reviews

Lodge Rosewood

"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 à disposition, si besoin. Boite à livres. Le lodge Rosewood n'est plus disponible sur vos dates, vous pouvez consulter l'annonce du "COUNTRY LODGE" 😉

Superhost

A villa's outdoor area is framed by wooden details and lush greenery. A private plunge pool is visible alongside a terrace. Large glass doors afford a view into the interior of the home, enhancing the connection between indoor and outdoor spaces.

Villa in Soufriere

4.93 out of 5 average rating, 405 reviews

Serrana Villa -Contemporary $1M Piton View Retreat

At Serrana Villa, style and grace are clearly evident in every aspect of this sophisticated 1-level, 2BR/2BA home. Located in Soufriere, the quintessential attraction capital of St. Lucia, Serrana 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. Come follow us ! @serranavillastlucia

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

4.96 out of 5 average rating, 143 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 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, 140 reviews

Mini Villa T1 Private Pool Sea View and Sea Access.

Turtle Bay Rentals Grande-Anse – Martinique Elevated studio mini villa with panoramic views of the sea and countryside. Sea access is a 50 m walk away. Beach known for its many green turtles visible in snorkel mask all year round. Composed of an air-conditioned bedroom, a shower room with toilet, an equipped kitchen on the covered terrace and a private 2 m*3 m pool on the uncovered terrace. TiSable restaurant 50 m away and small shops 500 m away.

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, 265 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

Top guest favorite

An open-air bathroom features wooden walls and flooring, complemented by natural stone accents. A rainfall showerhead is situated against a wood panel, with towels hung on a bamboo ladder. Baskets are neatly arranged on a rustic table, enhancing the organic design.

Bungalow in Saint-François

4.98 out of 5 average rating, 100 reviews

Blue Palm Residence - "Le Pavillon" - St François

Welcome to the PAVILION! We look forward to welcoming you to this recent and stylish 80m2 home with its private pool. Nestled in a quiet area of St François, it is located less than 5 minutes from the town center (shops, marina, golf, airfield, beaches...) The property benefits from a relaxing setting and natural ventilation. Ideal for a relaxing holiday.