Jump to: Room choices | Hotel description | Map | Amenities | Reviews
Choose Your Room
We recommend booking a stay with free cancellation in case your plans change.
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 $ 901 /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
Free Night Promotion
You have until March 19, 2026 to cancel this reservation without penalty.
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 $ 901 /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
Free Night Promotion
You have until March 19, 2026 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 $ 924 /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
Free Night Promotion
You have until March 19, 2026 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 $ 924 /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
Free Night Promotion
You have until March 19, 2026 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 $ 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
Free Night Promotion
You have until March 19, 2026 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 $ 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
Free Night Promotion
You have until March 19, 2026 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 $ 1,006 /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
Free Night Promotion
You have until March 19, 2026 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 $ 1,006 /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
Free Night Promotion
You have until March 19, 2026 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 March 19, 2026 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 $ 2,740 /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
Free Night Promotion
You have until March 19, 2026 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 $ 2,940 /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
Free Night Promotion
You have until March 19, 2026 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 $ 3,216 /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
Free Night Promotion
You have until March 19, 2026 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 $ 3,449 /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
Free Night Promotion
You have until March 19, 2026 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 $ 4,830 /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
Free Night Promotion
You have until March 19, 2026 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. Information and pricing is subject to change without notice. While we do our very best to ensure that information appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. Rates are quoted in USD, based on double occupancy, and are per room, per night, and include any free nights or other discounts, unless otherwise specified. Additional guests in the room, children, roll-away beds, and incidental charges may be at an additional cost.
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
Round Hill Is The Best
Round Hill is by far the best resort vacation we have ever had. We have returned every year in February or March for 35 years. Our children grew up there and now our grandchildren are growing up there. Our daughter was married there. What makes Round Hill so special is the staff. They are just wonderful. They care deeply about Round Hill and about the guests. We have seen many of them grow up at Round Hill. We have stayed in many of the villas and they are all wonderful. Kudos also to Jose Forstmayr, who is the Managing Director and does an absolutely first rate job of running the resort. If you're considering a Caribbean vacation, Round Hill is the place to go.
Max S
Great for gluten-free travelers!
Great getaway for 4 couples. Lots of activities and relaxation. Very spacious accommodations. Friendly, attentive staff. Really appreciated the attention to food allergies (ie Celiac friendly). Don't hesitate to book!
Cara B
Unique spirit of place with deep roots in location and people
great evening entertainment, music and dancing friendly attentive staff, perhaps why we keep coming back interesting cohort of solo travelers, couples, families and groups beautiful spa, gym and yoga pavilion romantic candlelight seaside dining
davidcK2895SP
Tired program and food and staff hiding again
Still the same tired chef offerings of bland food. Staff still doing as little as possible to assist you in the villas, often doing their own grocery shopping and laundry and will only dedicate 4 hours of their day to assist you, they also nap for 1-3 hours around lunch time or 3pm. Many of the gardeners like to hide on the lot with the drive way across from tennis and behind the staff house by the garden. Saturday gardeners were a no show for 2 weeks. The program for this resort is for years been high season Erika bloom and famous chefs, yet this does not offer full time luxury. It doesn't make sense and can't be fair to the local staff in fitness amd wellness. The Erika bloom lessons leave alot to be desired the trainers are not all polished and overpriced. The food is only good at this resort when a visiting chef is in charge whats that 12 days a year? Really tired of this, may sell the villa. Jamaica is very loud, it is constantly difficult to get a good night sleep. Please don't respond by requesting me to call or email, just monitor your staff, they act well for a week after you check on them then revert to the same games, and hire a better chef.
SaltyForbes - Austin, Texas
Wonderful old fashioned elegance
Old world charm The nicest staff- everyone feels like family, beautiful beach, stunning pool , large lovely rooms with great bathrooms… Everyone who works there seems happy and helpful
Safetravels68 - Vail, Colorado
Read more reviews or write a review
© 2026 TripAdvisor LLC. All rights reserved
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
