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Rooms

Breezy rooms and secluded villas, each a sanctuary of soft light, ocean views and timeless Caribbean style.

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Oceanfront Balcony King

Max 3 Occupancy • 43 m² / 460 ft²
These lower- floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Enjoy cozy, secluded balconies that make a perfect spot for morning coffee They are steps from the main infinity pool and white sand beach for guest convenience, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Oceanfront Balcony Double

Max 3 Occupancy • 43 m² / 460 ft²
These lower- floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Enjoy cozy, secluded balconies that make a perfect spot for morning coffee They are steps from the main infinity pool and white sand beach for guest convenience, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Ocean View Room King

Max 3 Occupancy • 43 m² / 460 ft²
These upper floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. They are steps from the main infinity pool and white sand beach for guest convenience. Enjoy towering cathedral ceilings and large, louvered windows that fold back to expose the turquoise sea, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Ocean View Double

Max 3 Occupancy • 43 m² / 460 ft²
These upper floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. They are steps from the main infinity pool and white sand beach for guest convenience. Enjoy towering cathedral ceilings and large, louvered windows that fold back to expose the turquoise sea, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Oceanview Room King

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same luxury style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The upper-level Premium Ocean View Rooms are located furthest from the pool and beach to provide a quieter, more secluded setting, while still being mere steps from these amenities. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Ocean View Room Double

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same luxury style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The upper-level Premium Ocean View Rooms are located furthest from the pool and beach to provide a quieter, more secluded setting, while still being mere steps from these amenities. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Oceanfront Balcony Room King

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The lower-level Premium Oceanfront Balcony Rooms have balconies that offer direct access to the pool, making it more convenient for guests to enjoy a refreshing swim. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Oceanfront Balcony Double

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The lower-level Premium Oceanfront Balcony Rooms have balconies that offer direct access to the pool, making it more convenient for guests to enjoy a refreshing swim. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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1 Bedroom Suite

Max 2 Occupancy • 101 m² / 1088 ft²
The spacious and uniquely designed One-Bedroom Suites are nestled into the hillside, surrounded by lush foliage, and brightly colored tropical blooms, with beautiful, elevated views of the Caribbean Sea. These Caribbean inspired luxury One-Bedroom Suites offer luxurious living and include spacious and exquisitely furnished bedrooms with king-size bed, separate living room for true indoor/outdoor living, with spectacular views of Round Hill Bay. Luxurious and spacious bathrooms, complete with a walk-in rain shower and separate soaking tub. Each One-Bedroom Suite features an outdoor private plunge pool complemented by tropical landscaping, the perfect spot to enjoy the cooling sea breeze as the sun sets. The One-Bedroom Suites are ideal for honeymooners or couples traveling on a romantic getaway, offering the ultimate in privacy and seclusion. Suites range from 1088 to 1968 sq ft.
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The One-Bedroom Suite

King Bed • up to 1800 sq ft
Nestled amid lush tropical foliage, these suites with one bedroom offer the ultimate in privacy and seclusion. Each features a spacious master bedroom, an airy living area, and a lavish bathroom with walk-in rain shower and soaking tub. Outside, a private plunge pool invites quiet moments of romance and relaxation with sunset views. Landscaped as a hideaway within the hillside, these suites are designed for luxurious living and complete serenity.
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Oceanfront Balcony Double

Max 3 Occupancy • 43 m² / 460 ft²
These lower- floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Enjoy cozy, secluded balconies that make a perfect spot for morning coffee They are steps from the main infinity pool and white sand beach for guest convenience, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Ocean View Room King

Max 3 Occupancy • 43 m² / 460 ft²
These upper floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. They are steps from the main infinity pool and white sand beach for guest convenience. Enjoy towering cathedral ceilings and large, louvered windows that fold back to expose the turquoise sea, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Ocean View Double

Max 3 Occupancy • 43 m² / 460 ft²
These upper floor rooms within the Pineapple House are impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, they blend style and comfort, and feature 460 sq ft of space, cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. They are steps from the main infinity pool and white sand beach for guest convenience. Enjoy towering cathedral ceilings and large, louvered windows that fold back to expose the turquoise sea, spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Oceanview Room King

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same luxury style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The upper-level Premium Ocean View Rooms are located furthest from the pool and beach to provide a quieter, more secluded setting, while still being mere steps from these amenities. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Ocean View Room Double

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same luxury style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The upper-level Premium Ocean View Rooms are located furthest from the pool and beach to provide a quieter, more secluded setting, while still being mere steps from these amenities. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Oceanfront Balcony Room King

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The lower-level Premium Oceanfront Balcony Rooms have balconies that offer direct access to the pool, making it more convenient for guests to enjoy a refreshing swim. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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Premium Oceanfront Balcony Double

Max 3 Occupancy • 43 m² / 460 ft²
These rooms represent the most requested accommodations within Pineapple House and provide the same style and comforts as the other accommodations, but with additional conveniences for an enhanced stay experience. The lower-level Premium Oceanfront Balcony Rooms have balconies that offer direct access to the pool, making it more convenient for guests to enjoy a refreshing swim. Impeccably designed by Ralph Lauren to evoke a crisp, clean Caribbean ambiance, these rooms blend style and comfort, and feature cool white stone floors, romantic four-poster bamboo beds and sumptuous upholstered furniture from the designer’s Home Collection. Guests will also enjoy spacious bathrooms with deep soaking tubs, freestanding rain shows and double vanities. Each room offers breath-taking views of Round Hill’s bay and underwater reef.
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The Classic Villas

from 1914 sq ft /178 sq m to 5816 sq ft /540 sq m • Two to Six Bedrooms
Celebrated as some of the Caribbean’s finest, Round Hill’s private luxury villas are designed to blend seamlessly with their lush hillside surroundings. Ranging from two to six bedrooms, each villa offers spacious indoor and outdoor living with private pools, outdoor showers, generous lounging areas, and elegant en-suite bathrooms. Reflecting the resort’s timeless charm, Classic Villas come with dedicated staff, daily in-villa breakfast, and a perfect balance of privacy, comfort, and effortless luxury.
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2 Bedroom Classic Villa w/o Pool

Max 4 Occupancy • 198 m² / 2130 ft²
Secluded for privacy, the Classic Villas at Round Hill offer guests an experience unique to the resort. These picturesque villas showcase the resort’s original style and classic elements and boast views of beautiful Round Hill Bay, while serving as the perfect home-away-from-home for guests. The Classic Villas come staffed with their own dedicated staff, helping maintain the historic resort’s unmatched level of luxury. These villas are equipped with two to five bedrooms and multiple open air living spaces, ensuring maximum comfort for honeymooners, families, or couples traveling together. Most Classic Villas are equipped with private pools while others are only steps away from the resort’s main pool. Guests also enjoy daily breakfast catered and served by their dedicated villa staff.
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2 Bedroom Classic Villa

Max 4 Occupancy • 181 m² / 1946 ft²
Secluded for privacy, the Classic Villas at Round Hill offer guests an experience unique to the resort. These picturesque villas showcase the resort’s original style and classic elements and boast views of beautiful Round Hill Bay, while serving as the perfect home-away-from-home for guests. The Classic Villas come staffed with their own dedicated staff, helping maintain the historic resort’s unmatched level of luxury. These villas are equipped with two to five bedrooms and multiple open air living spaces, ensuring maximum comfort for honeymooners, families, or couples traveling together. Most Classic Villas are equipped with private pools while others are only steps away from the resort’s main pool. Guests also enjoy daily breakfast catered and served by their dedicated villa staff.
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3 Bedroom Classic Villa

Max 6 Occupancy • 208 m² / 2235 ft²
Secluded for privacy, the Classic Villas at Round Hill offer guests an experience unique to the resort. These picturesque villas showcase the resort’s original style and classic elements and boast views of beautiful Round Hill Bay, while serving as the perfect home-away-from-home for guests. The Classic Villas come staffed with their own dedicated staff, helping maintain the historic resort’s unmatched level of luxury. These villas are equipped with two to five bedrooms and multiple open air living spaces, ensuring maximum comfort for honeymooners, families, or couples traveling together. Most Classic Villas are equipped with private pools while others are only steps away from the resort’s main pool. Guests also enjoy daily breakfast catered and served by their dedicated villa staff.
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4 Bedroom Classic Villa

Max 8 Occupancy • 315 m² / 3393 ft²,
Secluded for privacy, the Classic Villas at Round Hill offer guests an experience unique to the resort. These picturesque villas showcase the resort’s original style and classic elements and boast views of beautiful Round Hill Bay, while serving as the perfect home-away-from-home for guests. The Classic Villas come staffed with their own dedicated staff, helping maintain the historic resort’s unmatched level of luxury. These villas are equipped with two to five bedrooms and multiple open air living spaces, ensuring maximum comfort for honeymooners, families, or couples traveling together. Most Classic Villas are equipped with private pools while others are only steps away from the resort’s main pool. Guests also enjoy daily breakfast catered and served by their dedicated villa staff.
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5 Bedroom Classic Villa

Max 10 Occupancy • 540 m² / 5816 ft²,
Secluded for privacy, the Classic Villas at Round Hill offer guests an experience unique to the resort. These picturesque villas showcase the resort’s original style and classic elements and boast views of beautiful Round Hill Bay, while serving as the perfect home-away-from-home for guests. The Classic Villas come staffed with their own dedicated staff, helping maintain the historic resort’s unmatched level of luxury. These villas are equipped with two to five bedrooms and multiple open air living spaces, ensuring maximum comfort for honeymooners, families, or couples traveling together. Most Classic Villas are equipped with private pools while others are only steps away from the resort’s main pool. Guests also enjoy daily breakfast catered and served by their dedicated villa staff.
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5 Bedroom Estate Villa

Caribbean Sea view • Max 10 Occupancy
Serving as Round Hill’s crowning jewel, the Estate Villa is one of the most stunning villas on property. This magnificent five-bedroom villa is situated at the edge of the tropical rain forest, offering guests unmatched levels of privacy and seclusion, as well as some of the best views of the area. The Estate Villa comes with exceptional amenities, including a private pool, which can be heated upon request, and an open-air living space with both fire pit and waterfall. The villa is also equipped with five en-suite bathrooms, a powder room, several outdoor showers, a bar and sweeping views of the resort and Round Hill Bay. Guests also enjoy daily breakfast catered and served by their dedicated villa staff. The Estate Villa can accommodate up to fourteen guests, making it ideally suited for multi-generation families and large groups.
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3 Bedroom Signature Villa

Max 6 Occupancy • 282 m² / 3037 ft²
The Signature Villas at Round Hill offer guests their own private experience. Each unique villa provides guests with indoor and outdoor living spaces, designed with a blend of modern and classic cottage elements, with stylish open-air and enclosed living rooms. Guests can enjoy their own private pool surrounded by beautifully landscaped gardens. The villas come staffed with their own dedicated staff, who help maintain Round Hill’s high level of service. Guests also enjoy daily breakfast catered and served by the villa staff. Signature villas range from three to six bedrooms, making them ideally suited for families or intimate groups.
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4 Bedroom Signature Villa

Max 8 Occupancy • 402 m² / 4326 ft²
The Signature Villas at Round Hill offer guests their own private experience. Each unique villa provides guests with indoor and outdoor living spaces, designed with a blend of modern and classic cottage elements, with stylish open-air and enclosed living rooms. Guests can enjoy their own private pool surrounded by beautifully landscaped gardens. The villas come staffed with their own dedicated staff, who help maintain Round Hill’s high level of service. Guests also enjoy daily breakfast catered and served by the villa staff. Signature villas range from three to six bedrooms, making them ideally suited for families or intimate groups.
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5 Bedroom Signature Villa

Max 10 Occupancy • 566 m² / 6095 ft²
The Signature Villas at Round Hill offer guests their own private experience. Each unique villa provides guests with indoor and outdoor living spaces, designed with a blend of modern and classic cottage elements, with stylish open-air and enclosed living rooms. Guests can enjoy their own private pool surrounded by beautifully landscaped gardens. The villas come staffed with their own dedicated staff, who help maintain Round Hill’s high level of service. Guests also enjoy daily breakfast catered and served by the villa staff. Signature villas range from three to six bedrooms, making them ideally suited for families or intimate groups.
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6 Bedroom Signature Villa

Max 12 Occupancy • 566 m² / 6095 ft²
The Signature Villas at Round Hill offer guests their own private experience. Each unique villa provides guests with indoor and outdoor living spaces, designed with a blend of modern and classic cottage elements, with stylish open-air and enclosed living rooms. Guests can enjoy their own private pool surrounded by beautifully landscaped gardens. The villas come staffed with their own dedicated staff, who help maintain Round Hill’s high level of service. Guests also enjoy daily breakfast catered and served by the villa staff. Signature villas range from three to six bedrooms, making them ideally suited for families or intimate groups.
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The Estate Villa

Sleeps 12 • 8850 sq ft / 822 sq m
Perched beside a tropical rainforest, Round Hill’s Estate Villa is the resort’s ultimate retreat, offering unparalleled privacy and seclusion. With five or six bedrooms, two pools, multiple open-air living areas, a bar, and a waterfall, the villa is surrounded by breathtaking views of Round Hill Bay. Perfect for large families or reunions, it comes with dedicated staff who arrange daily breakfasts and provide attentive, genuine Jamaican hospitality.
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The Signature Villas

Three to Six Bedrooms • from 3037 sq ft / 282 sq m to 8024 sq ft /745 sq m
Round Hill’s Signature Villas redefine exclusivity, combining elegant indoor spaces with open-air living that celebrates both modern luxury and classic Caribbean style. Set amid beautifully landscaped gardens, these larger villas with three to six bedrooms feature a private pool and versatile living areas, ideal for families or small groups. Every stay includes a daily gourmet breakfast, prepared with care by your dedicated villa staff.