Vacation rentals in Windy Hill

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Top-rated vacation rentals in Windy Hill

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Guest favorite

An aerial view of the villa showcases a sparkling swimming pool surrounded by lush garden areas. Vibrant palm trees gently sway in the breeze, and the clear turquoise waters of the Caribbean Sea extend to the horizon, complementing the tranquil setting.

Villa in Fryers Well Point Bay

5 out of 5 average rating, 14 reviews

Oceanfront House, Pool, Gardens - Freyers Well Bay

Freyers Well Bay House is a stunning oceanfront Barbadian-style villa offering panoramic views of the Caribbean Sea. Located a 10 min drive north from charming Speightstown, this is the ultimate tropical paradise with dining, supermarkets, and attractions nearby. Relax by your private pool, stroll through the large gardens or head down to the beach - this is the kind of villa where memories are made. The villa, pool, manicured lawns and tropical gardens privately located on over an acre of land

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Guest favorite

A large balcony features a plunge pool, colorful beach balls resting on the edge. A blue hammock is suspended nearby, with views of the ocean and palm trees under a clear sky, creating a serene atmosphere for relaxation.

Home in Bathsheba

4.81 out of 5 average rating, 147 reviews

Tranquil/4 King Bed/Plunge Pool/East Coast/RecRoom

Perched on a hillside, this beautiful home offers sweeping 180-degree ocean views of Barbados’ rugged east coast. A peaceful beach is just a three-minute walk away, ideal for long strolls, shell collecting, and unwinding. With four bedrooms (three en suite), the home is perfect for families or groups, offering privacy alongside generous shared spaces. Sunrise is a highlight—enjoy coffee, yoga, or meditation on the upper balcony as the ocean awakens with the soothing sound of crashing waves.

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Top guest favorite

The expansive swimming pool showcases serene blue waters, bordered by tropical greenery and lounge chairs. A clubhouse with a thatched roof is visible, while vibrant clouds fill the sky, reflecting soft hues of orange and purple as the sun sets over the ocean.

Vacation home in Mount Standfast

5 out of 5 average rating, 22 reviews

Interior Designed 2 Bedroom 2 Bathroom Apartment

✨ Relax on the West Coast of Barbados ✨ Stay in a newly renovated (2022) apartment at the exclusive Sugar Hill Resort, a gated community perched on a ridge with sea views from the clubhouse and tropical garden/pool views from your balcony. Bedrooms open onto a balcony overlooking lush gardens & pool Complimentary beach chairs & umbrellas. Just 5 minutes to Holetown’s restaurants, shops & nightlife Perfect for couples, families, or friends looking for comfort, convenience, and Caribbean charm.

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Guest favorite

A charming two-story cottage is set against a lush green landscape. The wooden exterior is complemented by a red roof, with a set of stairs leading to a welcoming porch. Tropical plants are visible in the foreground, adding to the serene environment.

Cottage in Bathsheba

4.92 out of 5 average rating, 39 reviews

PamRu - Cozy Cottage with Breathtaking Views

Welcome to our charming cottage in the heart of Bathsheba, Barbados. Just steps away from the Soup Bowl surf break, our cottage offers a blend of rustic tranquility and coastal adventure. Wake up to the soothing sound of ocean waves and enjoy breathtaking sunrise views from your private deck. Whether you’re a surfer seeking the perfect wave or a traveler or local looking for a serene escape, our cottage is the ideal place to unwind and experience the true beauty of Barbados’ rugged east coast.

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Guest favorite

A modern open-concept living space is presented, featuring neutral tones and natural materials. The fully equipped kitchen includes a large island with a sink, complemented by stylish pendant lighting. Floor-to-ceiling glass doors open to a private outdoor seating area, enhancing the airy ambiance.

Home in Lower Carlton

5 out of 5 average rating, 14 reviews

The Carlton Barbados - Luxury Townhouse Rental

The Carlton is a luxury townhouse near Barbados' west coast beaches. Enjoy the 2,063 sq ft space which includes 3 bedrooms, 3 bathrooms, private plunge pool, outdoor soaking tub, and easy access to dining, shopping, and nightlife in Holetown and Speightstown. Enhance your stay with VIP perks like private yacht charters, a Mount Gay Rum tour, and chef-curated dining. Whether relaxing or exploring, The Carlton delivers the best of both worlds. Book your unforgettable Barbadian escape today!

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Guest favorite

A beach house sits proudly with a vibrant blue exterior and a spacious balcony overlooking the surroundings. Palm trees gently sway in the breeze, creating a relaxed atmosphere. The elevated structure features an open space underneath, with a car parked in the driveway.

Cottage in Bathsheba

4.96 out of 5 average rating, 52 reviews

Modern, Relaxing Beach House with Panoramic View

Wake up to a beautiful sunrise in the heart of Bathsheba! Situated near Barbados' most famous rock, our relaxing beach house is perfect for an individual, family or friends. Sit on the patio and take in the panoramic view, while listening to the soothing waves of the Atlantic Ocean. This seaside getaway is within walking distance of restaurants specialising in local cuisine. Convenience store and attractions nearby. Ideal for surfers. Situated on a bus route with frequent service.

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Superhost

Cottage in Foster Hall

4.78 out of 5 average rating, 90 reviews

SeaRenity Abode: Rest & Reset Retreat

Discover peace and relaxation at SeaRenity Abode, a newly updated 3BR/2BA coastal cottage featuring a modern coastal aesthetic with refreshed décor, airy neutral tones, and stylish, comfortable furnishings—plus AC to keep you cool! Enjoy the outdoor lounging areas by the pool or on the patio—perfect for morning coffee, evening breezes, or simply soaking in the peaceful surroundings and stunning Atlantic Ocean views. It’s the perfect place to relax, reset, and renew.

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Top guest favorite

Home in Speightstown

5 out of 5 average rating, 18 reviews

Waterfront/Beach/Resort Access/Airport Transfer

Recently refurbished waterfront 3-bedroom townhouse in the exclusive Port St. Charles Resort & Yacht Club. Perfect for families, couples or friends. Features: • 3 king bedrooms with en-suite bathrooms • Fully equipped kitchen • Private plunge pool • Outdoor dining & loungers • Washer & dryer Resort amenities: • Beach with chairs & umbrellas • Gym, restaurants & bars • Complimentary water taxi Bonus: Complimentary airport transfer from airport to the apartment.

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Guest favorite

A spacious studio apartment features a wooden bed with soft linens and two patterned armchairs. Natural light floods the room through large windows, illuminating the textured stone walls and exposed wooden beams on the ceiling. A small dining area is visible in the adjacent space.

Apartment in Black Bess

4.82 out of 5 average rating, 113 reviews

The Loft at Ridge View

The Loft at Ridge View is a cosy countryside escape in St. Peter, Barbados—5 minutes from Haymans Market and 10 minutes from Speightstown. This top-floor studio sits on a ridge overlooking the west coast, offering stunning sea views and unforgettable sunsets. Surrounded by nature and local life, it invites slow living, cultural immersion, and relaxation. Amenities such as a pool, garden, A/C and dedicated parking make it the perfect island retreat.

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Superhost

Villa in Holetown

5 out of 5 average rating, 3 reviews

Kokomo - The Island Retreat: Luxury 4BR Pool Villa

Villa Kokomo is a newly constructed, 4-bedroom, 4,5-bathroom luxury property located in the heart of Sunset Crest, Holetown, on the prestigious West Coast. Situated within walking distance of beaches, Limegrove Lifestyle Centre, Massy Supermarket, 24h Rubis Gas Station, Chattel Village with its lovely shops and several restaurants and bars, it features a private pool, modern kitchen, and air-conditioned, single-level living.

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Guest favorite

A view from the patio features a wooden table and chairs, with the Atlantic Ocean visible in the distance beyond swaying palms. Large louvered windows allow fresh air and light, framing a serene coastal landscape.

Home in Saint Joseph

4.91 out of 5 average rating, 94 reviews

Beyond "the upper floor" a Paradise in Barbados

Available after a major refurbishment, in the wild side of the island right in front of the Atlantic Ocean a little piece of paradise to spend a piecefull vacation away from "the world". Two Bedrooms King and Queen, two bathrooms newly renovated, kichen and living room a great patio at two minutes walk from the beach. We offer high speed wifi. Our maid is available to guests every morning until 12 five days a week.

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Top guest favorite

The exterior of the pink house is visible, showcasing a welcoming entrance with stairs leading to the front door. Two vehicles are parked in the driveway. Lush green trees and palm plants frame the property, and a clear blue sky is seen above.

Apartment in Bathsheba

4.98 out of 5 average rating, 42 reviews

Cozy Bathsheba

Are you looking for a budget friendly accommodation that can suite a group of four ? Well look no more this apartment is just five minutes walk from the Bathsheba beach . It has two bedrooms that can accommodate four persons. The area is also near the soup bowl where the international surfing competition is held. It has a living room, dining area, a kitchen and a bathroom.

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