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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 $ 713 /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 October 5, 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 $ 713 /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 October 5, 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 $ 738 /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 October 5, 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 $ 738 /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 October 5, 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 $ 759 /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 October 5, 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 $ 759 /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 October 5, 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 $ 1,060 /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 October 5, 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 $ 1,060 /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 October 5, 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 $ 1,624 /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 October 5, 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 $ 2,679 /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 October 5, 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 $ 2,934 /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 October 5, 2025 to cancel this reservation without penalty.
4-Bedroom Classic Villa
- 8 People Max
- 3393 sq feet (315 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 $ 3,104 /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 October 5, 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 $ 3,232 /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 October 5, 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 $ 3,402 /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 October 5, 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 $ 3,657 /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 October 5, 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 $ 4,337 /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 October 5, 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
Awful food
Food awful need a new chef, staff hiding and not working at houses. Another hotel claiming they pull substantial produce from their on property garden.
SaltyForbes
Must see resort!
The most magical and special resort! It’s one of those pinch me moments where it didn’t feel real. The staff and quality of the food was outstanding. Everyone was so pleasant and genuinely kind. I can’t wait to go back!
W2693BLamandab
Another amazing stay!
What an amazing stay again at this beautiful resort. The villa with private pool had breathtaking views of The Caribbean Sea and the lush gardens. Thank you for the fantastic staff making our stay so wonderful :-) Wade, Khaleel, Junior walker, Tash, Owen, Birch, Dahlia, Joy, Morgan, Oshan, Brandon, Fitzroy, Neil, Ashanee, Ashe and more! Thank you Josef for your hospitality! We look forward to next year anniversary celebration :-).
Travel19702014
High end family vacation that doesn't disappoint
We rented a 3 bed signature villa for our recent stay, and absolutely loved our time at Round Hill. It felt boutique, with plenty of space for us to enjoy the resort without it feeling crowded. Having breakfast prepared for us each morning at our villa, next to the pool and looking out over the Caribbean Sea was the best way to start each day. The villa was exceptionally clean, as was our pool and rest of the resort, and everything felt well maintained and cared for. The restaurant served a different menu every night, however Monday's beach BBQ was definitely the highlight for all of us, and something that shouldn't be missed. The gym was well equipped for strength training and cooled appropriately for a workout. I was able to do my usual routine with the machines and free weights available. The kids absolutely loved the water sports! Tubing was a highlight for them, and the wife and I really enjoyed the snorkelling accessible straight from the beach with the house reef only a short distance from the shore. And the spa massages we had on our last full day were also top notch! Highly recommended stay for families.
Jason F - Flitwick, United Kingdom
Great resort!
Amazing! Would absolutely return. The bills experience is a must. The staff are amazing. The views are miraculous. Great accommodations for kids as well.
BN M
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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
