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Choose Your Room
We recommend booking a stay with free cancellation in case your plans change.
Ocean View Room -King
- 3 People Max
- 460 sq feet (43 sq meters)
- 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 feet 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
USD $ 909 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Ocean View Room Double
- 3 People Max
- 460 sq feet (43 sq meters)
- 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 feet 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
USD $ 909 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Premium Oceanview Room-Double
- 3 People Max
- 460 sq feet (43 sq meters)
- 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
USD $ 941 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Premium Oceanview Room -King
- 3 People Max
- 460 sq feet (43 sq meters)
- 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
USD $ 941 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Oceanfront Balcony Room Double
- 3 People Max
- 460 sq feet (43 sq meters)
- 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 feet 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
USD $ 969 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Oceanfront Balcony Room King
- 3 People Max
- 460 sq feet (43 sq meters)
- 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 feet 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
USD $ 969 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Premium Oceanfront Balcony Room -Double
- 3 People Max
- 460 sq feet (43 sq meters)
- 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
USD $ 1,080 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Premium Oceanfront Balcony Room-King
- 3 People Max
- 460 sq feet (43 sq meters)
- 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
USD $ 1,080 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
One Bedroom Suite
- 3 People Max
- 1088 sq feet (101 sq meters)
- 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
BEST FLEXIBLE RATE
You have until May 31, 2025 to cancel this reservation without penalty.
2-Bedroom Classic Villa no pool
- 4 People Max
- 2130 sq feet (198 sq meters)
- 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
USD $ 2,519 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
2-Bedroom Classic Villa
- 4 People Max
- 1946 sq feet (181 sq meters)
- 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
USD $ 2,769 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
3-Bedroom Classic Villa
- 6 People Max
- 2235 sq feet (208 sq meters)
- 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
USD $ 2,969 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
3-Bedroom Signature Villa
- 6 People Max
- 3037 sq feet (282 sq meters)
- 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
USD $ 3,269 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
5 Bedroom Classic Villa
- 10 People Max
- 5816 sq feet (540 sq meters)
- 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
USD $ 3,859 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
4-Bedroom Signature Villa
- 8 People Max
- 4326 sq feet (402 sq meters)
- 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
USD $ 4,059 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
5-Bedroom Signature Villa
- 10 People Max
- 6095 sq feet (566 sq meters)
- 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
USD $ 5,678 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
6-Bedroom Signature Villa
- 12 People Max
- 6595 sq feet (613 sq meters)
- 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
USD $ 7,227 /nt
Signature Perks Package
- • Full Breakfast for two daily in The Grille Restaurant, the guest's villa or through room services (Delivery charge applies)
- • $100 Spa Credit per room, per stay
- • Welcome Amenity
- See all the perks
You have until May 31, 2025 to cancel this reservation without penalty.
Please note, room photos and descriptions are representative of the room category. Actual rooms may vary from what is shown. Upgrades, early check-in, and late check-out are based on availability.
About the Hotel
Originally opened in 1953 on the sugar-white sands of Montego Bay, Round Hill Hotel and Villas has become a modern day icon of style and taste in Jamaica. Brimming with simple, understated elegance, the property exudes a timeless glamour that has attracted prominent socialites, dignitaries, and artists to its beach club, accommodations, and retro-chic spaces. Among its celebrated guests is internationally acclaimed designer Ralph Lauren, who has lent his classical style to the entire property, including his signature 36-room remarkable villa, The Pineapple House. Whether your stay is in a sun-kissed guest suite or a complete villa, amenities are top notch, including private verandas, expansive floor plans, iPhone docks, and wireless Internet access. Plus, with a world-class oceanfront spa ready to transport you to a sublime sanctuary, this resort is not short on anything when it comes to the pampered lifestyle. From the abundance of genuinely warm hospitality that Jamaica is famous for, to the luxurious surroundings at every turn, expect a supremely fantastic retreat at Round Hill Hotel and Villas, one of the most beautiful places on earth.
Location
Round Hill Hotel and Villas
John Pringle Drive
P.O. Box 64
Montego Bay, Jamaica
Nearest Airport: MBJ
Features and Amenities
- General Information
- Non-Smoking Rooms
- Dining
- Outdoor Dining
- Restaurant
- Room Service
- Bar & Lounge
- Afternoon Tea
- On-Site Amenities
- Salon
- Concierge
- Spa on Property
- Laundry Service
- Library
- Gift Shop
- Fitness Center
- Private Beach
- WiFi
- Live Entertainment
- Outdoor Pool
- Tennis Courts
- Outdoor Whirlpool
- Jogging Path
- In-Room Amenities
- Private Patios or Balconies
- Air Conditioning
- Direct Dial Telephones
- In-Room Safes
- iPod Docks
- Coffee & Tea Facilities
- Pillow Menu
- Radio & CD Players
- Rain Showers
- Activities
- Deep Sea Fishing
- Kayaking
- Sailing
- Tennis
- Water Skiing
- Windsurfing
- Scuba Diving
- Snorkeling
- Sunset Cruises
- Nature Walks
- Basketball
- Yachting
- Business
- Business Center/Services
- Meeting Rooms
- Family
- Cribs
- Babysitting
- Kids Club
- Highchairs
- Children's Menus
- Nearby
- Restaurants
- Golf
- Interests
- Beach
- Honeymoons & Romance
- Signature Perks
- Spa
Reviews for Round Hill Hotel and Villas
Another Epic visit!
Round Hill is a timeless iconic boutique resort. It is a step back in time when guests were royally treated and appreciated. The kind notes from the front desk staff and the General Manager Josef say it best "Welcome Home." That warm greeting understates the feeling you get experiencing a Round Hill stay. The accommodations, staff, restaurant, cuisine, spa, beach, and activities are first rate. Your choices are Ralph Lauren designed room suites or entire Villas that come with a maid who makes you breakfast in the morning! All this executed by an extraordinary caring staff! Looking forward to many more future memories there!
georgesS7506UH - Boca Raton, Florida
Five Star Experience!!
Round hill was amazing and exceeded our expectations! The resort was compact and easy to get around. The room was perfect and the shared spaces are beautiful. The service was mainly great - shout out to Larry and his crew at the pool bar - they were wonderful!! I think Jackie at breakfast may have been having a bad week but every single other person we encountered was great! The managers reception on Wed night was lovely. And the food, my husband can’t stop talking about it. Truly a give star experience. Our one thing for improvement would be a better wifi signal around the resort. Also complimentary sunscreen would be a nice touch. Yeah Mon!
lindseyl435 - Pittsburgh, Pennsylvania
Incredible High End Resort that was all we hoped it would be and more!
One of the most amazing resorts I have ever visited. The resort is beautiful and high end, but still felt warm and welcoming. The staff is amazing and really adds to the experience. The beach was wonderful and the infinity pool was incredible! The resort is expensive but worth it. And the food was wonderful as well. We will be back!
cherylo638 - Whitehouse, Ohio
Amazing Place!
The Round hill is AMAZING!! A must go. Everything there is perfect, staff, food, hospitality, accommodations, beaches and water. From the beginning when you arrive to the airport, to the drive there, then being welcomed at the resort, everyone who works there are so friendly and very hospitable. If you go there, you will want to stay longer, we are already planning a return trip in a few months.
Keith B - Hilton Head, South Carolina
Jamaica for the discriminating travelers
Stunning property staffed by the best of the best. Luxury on every level. Food, aesthetics, privacy, personal service, views, awesome pools, top notch spa and gym. For foodies we ended up never leaving the property for a meal as every day was creative and fantastic
Deb B
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We were the lucky winners of two of your auctions. The first one was a package to Round Hill Hotel and Villas in Jamaica. What a wonderful place that is. We were treated royally and given one of the more beautiful villas overlooking the ocean. The food and attentiveness of this lovely resort was excellent! We will be going back and taking some friends as well. High points for Round Hill Hotel and Villas!!
-P. & T. Gregory
My wife and I had a great stay at Round Hill Hotel and Villas in Jamaica. The accommodations were excellent. On our arrival, we were upgraded to a villa that overlooked the sea. Every morning we just sat up in bed and enjoyed the peaceful view. The Round Hill staff was excellent - they catered to our every need and treated us like royalty. The food was fantastic. We had cooks come to our villa and make breakfast and serve us on the terrace. It was a vacation my wife and I will cherish forever.
-T. & J. Miller
My husband and I enjoyed a five-day vacation at Round Hill Hotel in Montego Bay, Jamaica - a magnificent retreat frequented by the truly privileged. We were pampered beyond our expectations. Thank you for making this dream a reality.
-E. Barr
