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Holiday rentals in Leeward Islands

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Top-rated holiday rentals in Leeward Islands

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Top guest favourite
A serene outdoor space features a modern freestanding bathtub overlooking the ocean. A stylish hanging chair is positioned nearby, surrounded by potted plants. Natural light illuminates the deck, enhancing the views of the landscape and sea beyond.
Tiny home in Willoughby Bay
4.97 out of 5 average rating, 112 reviews

Cozy Stargazer Pod - Ocean View/No Cleaning Fee

Escape the ordinary vacation; immerse yourself in nature and reconnect with your body's natural rhythm. At Coastal Escape Antigua's stargazer pod, experience vacationing at its romantic, luxurious best overlooking breathtaking Willoughby Bay. This unique getaway is perfect to recharge from the stresses of life or to reconnect with that special someone. There are no alarm clocks here; natures orchestra of birds, crickets and grasshoppers will lull you to sleep and welcome you into the new day.

Guest favourite
The open living area features a comfortable seating arrangement with plush cushions, accompanied by a decorative coffee table adorned with tropical flowers. The kitchen, visible in the background, is bright and equipped with basic cooking utensils. Large windows allow for natural light and scenic views of the surrounding greenery.
Cottage in Falmouth
4.94 out of 5 average rating, 134 reviews

Cleopatra - English Harbour

Cleopatra is a large, open, one-bedroom cottage with comfortable lounge, King bed, and kitchen on Pineapple House property in English Harbour. Our favorite amongst several cottages, everything is in white; everything is open, & the kitchen is big. Stunning view of Super Yachts in Falmouth Harbour. Gated Community. Wi-fi. Night life. Restaurants. Spas. Activities. Steps from Nelson's Dockyard. Steps from Pigeon Beach, where there are two beach bars. Houseskeeping Services. Open October to May.

Top guest favourite
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.
Guest house
4.96 out of 5 average rating, 180 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 favourite
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.

Superhost
An indoor living space features a wooden table surrounded by cushioned seating. Light filters through handmade glass bricks, creating colorful patterns. An arched doorway leads to a kitchen area, while large windows provide views of the lush garden outside.
Cottage
4.9 out of 5 average rating, 105 reviews

Lower Love. Ecolodge in tropical garden, Dominica

Prepare for a truly magical holiday in Dominica. 100% off grid, solar powered, gravity rain fed, yet with satellite internet, this architect designed ecolodge invites you to relax and rejuvenate. The stunning inside-outside living room is the perfect place to watch the hummingbirds as you sip a fresh coffee. Surrounded by a lush tropical garden, yet within walking distance of Soufriere and the Caribbean sea. Get away from it all in this breathtaking setting, the Nature Island at its best.

Top guest favourite
A wooden walkway leads towards a bright bungalow, framed by a lush green landscape. Tropical plants and colorful flowers adorn the pathway, while the distant ocean can be seen under a clear blue sky. Sunlight illuminates the vibrant surroundings.
Bungalow
4.95 out of 5 average rating, 104 reviews

"Carambole" Bungalow sea view private pool

Welcome to Carambole and Pineapple, your little corner of heaven nestled in the heart of the banana trees. This intimate set of 2 brand new bungalows offers magnificent views of the breathtaking Grande Anse Bay. Ideally located on a private property, 5 minutes' walk to the beach, on the first heights of Deshaies, they will guarantee you change of scenery, privacy, calm and tranquility. Come and admire the sublime sunsets from your private pool by tasting a tasty planter

Guest favourite
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, 166 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.

Top guest favourite
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, 258 reviews

Atypical Rosewood Lodge with sea view

"LODGE ROSEWOOD": In the heart of a tropical garden with views of the Caribbean Sea and the mountain. Charming 🤩accommodation for 2 people.🥰 1 double bedroom (bed 160x200 or 2 beds 80x200), shower room, toilet, kitchen, dining area, deck with deckchairs. A planter and welcome accras are offered Masks, snorkels, fins available, if needed. Book box. The Rosewood lodge is no longer available on your dates, you can consult the "COUNTRY LODGE" listing 😉

Top guest favourite
The exterior of Boulder Cottage showcases a covered patio area with wooden louvers, overlooking Falmouth Harbour. Lush greenery and stone accents frame the scene, while the tranquil water and sailing boats are visible in the background under a softly lit sky.
Cottage in Cobbs Cross Hill
4.95 out of 5 average rating, 179 reviews

Private cottage stunning view!

Nestled in a woodland forest overlooking Falmouth Harbour, 10 min from Historic Nelsons Dockyard, 3 Marinas, Beach and all amenities. Boulder Cottage is very private, has a King sized bed, full kitchen, patio dining, plunge pool and stunning views! Also on property is Antilles Stillhouse, a Craft Distillery! The first of its kind in the region, David, master distiller, focuses on making high quality spirits utilising local botanicals.

Top guest favourite
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, 280 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

Guest favourite
A scenic balcony view features a hammock and lush greenery overlooking the valley. Majestic mountains are visible in the distance against a colorful sunset sky, enhancing the tranquil atmosphere of the surrounding landscape.
Tiny home in Vermont
4.9 out of 5 average rating, 145 reviews

Spirit of the Valley - Strong's House

Pine house on rainforest edge Queen Bed Superior mattress Mosquito net Outstanding views valley/sea/gardens WIFI Comfortable, rustic, clean Tranquil setting Can be very windy Good for hikers, birders, yogis Daybed Hike: Vermont Trail, 'Vincy' parrot Bush Bar 10 mins. Table Rock 1 hr Drive: Superb snorkelling site 45 mins. Provided: Soap Salt, pepper Instant coffee 1 towel each Cafetiere

Guest favourite
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 in Soufriere
4.98 out of 5 average rating, 141 reviews

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.

Popular amenities for Leeward Islands holiday rentals