Vacation rentals in Windy Hill

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Top-rated vacation rentals in Windy Hill

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

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Top guest favorite

An expansive rooftop deck features an infinity-edge pool overlooking the turquoise Caribbean Sea. Lounge chairs are positioned around the pool, offering a relaxing space to enjoy stunning ocean views and the distant shoreline.

Apartment in Bridgetown

5 out of 5 average rating, 58 reviews

Beachfront Luxury at Allure | Stunning Ocean Views

Set directly on the beachfront, this luxury Barbados escape offers uninterrupted ocean views and the rare experience of stepping straight from your door onto soft white sand. Designed for comfort, style and relaxation. This space features a 2-bedroom, 2 1/2-bathroom condo nestled on its prime location on one of the island’s most beautiful stretches of coastline within a secure gated community. A perfect winter escape for those looking to trade colder months for warm, sun-soaked days by the sea.

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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

4.8 out of 5 average rating, 148 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 kitchen features sleek white cabinetry and stainless-steel appliances. A spacious island with seating for six is positioned at the center, while large windows provide natural light and views of the surrounding palm trees.

Home in Bathsheba

4.91 out of 5 average rating, 45 reviews

Brees Beach House Upper - Bathsheba

Welcome to Brees Beach House! This beach front property, located in the heart of Bathsheba and directly in front of Barbados’s world-famous surf break, Soup Bowl, is perfectly suited for everyone – from surf trippers to families and retirees. Enjoy the quaint, rustic, and peaceful surf village featuring cool breezes, stunning views, and mouth-watering, local restaurants and rum-shops, all within walking distance. You’ll be hard pressed to find better local food than what the East Coast offers!

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Top guest favorite

A view of a tranquil beach features soft white sand meeting calm, aquamarine waters. Lush tropical landscaping surrounds a charming cottage in the background. Palm trees sway gently, providing a serene atmosphere, with a bright sky and distant greenery enhancing the coastal scenery.

Cottage in Freshwater Bay

4.98 out of 5 average rating, 63 reviews

Beach front cottage (2 bed / 2 bath)

This is a charming 2 bedroom 2 bathroom cottage surrounded by beautifully tropical landscaped gardens with private access to one of the prettiest white sand beaches on the Barbados coastline offering ideal swimming conditions in the calm, aquamarine blue waters of the Caribbean Sea and picture perfect sunset views one never tires of. The address is Freshwater Bay but to the locals it’s known as Paradise Beach and when you get here you’ll agree. It is the ideal island living experience.

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Guest favorite

A spacious outdoor living area features comfortable seating and a dining table surrounded by natural light. Lush greenery and ocean views are visible in the background, creating a relaxing environment. Ceiling fans provide airflow above the seating arrangement.

Home in Speightstown

4.96 out of 5 average rating, 57 reviews

Steps to Beach, Ocean View, Pool & Resort Access!

The best location in Barbados, surrounded by sugary-white sandy beaches, fabulous restaurants & shops. Relax in the sparkling pool, savor breathtaking views & enjoy the comfort of a spacious tropical sanctuary. ⭐ “We are frequent visitors to Barbados and can honestly say this has been our best experience yet!” 🏖 HIGHLIGHTS ✓ FREE access to the gorgeous beachfront Fairmont Beach Club ✓ Amazing sunsets & newly built for "open-air" living ✓ 5-stars for clean, spacious & comfy

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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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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, 114 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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