Round Hill Hotel and Villas

Montego Bay, Jamaica

9.3 First Class

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Choose Your Room

We recommend booking a stay with free cancellation in case your plans change.

OCV
Ocean View Room Double, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $612 /nt
$2,305 for 3 nights
including taxes & fees
Price breakdown

DOV
Ocean View Room -King, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $612 /nt
$2,305 for 3 nights
including taxes & fees
Price breakdown

SOK
Premium Oceanview Room -King, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $641 /nt
$2,413 for 3 nights
including taxes & fees
Price breakdown

MOV
Premium Oceanview Room-Double, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $641 /nt
$2,413 for 3 nights
including taxes & fees
Price breakdown

OCF
Oceanfront Balcony Room King, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $689 /nt
$2,594 for 3 nights
including taxes & fees
Price breakdown

OV2
Oceanfront Balcony Room Double, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $689 /nt
$2,594 for 3 nights
including taxes & fees
Price breakdown

LO1
Premium Oceanfront Balcony Room -Double, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $710 /nt
$2,674 for 3 nights
including taxes & fees
Price breakdown

NOD
Premium Oceanfront Balcony Room-King, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $710 /nt
$2,674 for 3 nights
including taxes & fees
Price breakdown

SU1
One Bedroom Suite, at Round Hill Hotel and Villas

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

USD $ 1,241 /nt

Limited availability.

BEST FLEXIBLE RATE

You have until August 2, 2025 to cancel this reservation without penalty.

USD $1,241 /nt
$4,664 for 3 nights
including taxes & fees
Price breakdown

VB2
2-Bedroom Classic Villa no pool, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $1,267 /nt
$4,775 for 3 nights
including taxes & fees
Price breakdown

BKV
3-Bedroom Classic Villa, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $1,803 /nt
$6,797 for 3 nights
including taxes & fees
Price breakdown

OV3
3-Bedroom Signature Villa, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $2,058 /nt
$7,753 for 3 nights
including taxes & fees
Price breakdown

VL4
4-Bedroom Classic Villa, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $2,238 /nt
$8,440 for 3 nights
including taxes & fees
Price breakdown

VA4
4-Bedroom Signature Villa, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $2,536 /nt
$9,556 for 3 nights
including taxes & fees
Price breakdown

VL5
5-Bedroom Signature Villa, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $4,426 /nt
$16,658 for 3 nights
including taxes & fees
Price breakdown

VLO
6-Bedroom Signature Villa, at Round Hill Hotel and Villas

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

  • • 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 

You have until August 2, 2025 to cancel this reservation without penalty.

USD $5,106 /nt
$19,220 for 3 nights
including taxes & fees
Price breakdown

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

Wonderful week, not sure we would book again...

TripAdvisor Traveler Review Rating Reviewed 22 hours ago

Round Hill is lovely and you can tell from being there it is a place families return again and again. Staff is fantastic and we enjoyed every interaction with each of them. Overall, there is a premium exacted at every turn, which we don't love. Staying at expensive places, you sort of know what you're getting into but here it felt a little bit extra...there are so many staff catering to you, which is nice but there is a definite air of expectation that you are tipping each one of them - AND there is a 10% tax and 18.5% gratuity on most everything...but staff will say that gets split amongst everyone so then tipping on top of that becomes routine. We were told that prices went up a little over a year ago and with what we spent for 1 week here, not sure we would go back when there are so many other wonderful options. What you get for the money perhaps feels a bit more 'in line' elsewhere, unless you had the sense of nostalgia for this place, which we do not.

76kristena


One of the best resorts ever!

TripAdvisor Traveler Review Rating Reviewed 1 day ago

The hotel rooms, beds, villas, staff, views, beach and pool…really this property is amazingly beautiful with exceptional service!

Nadine C


Amazing Authentic Jamaican Hotel

TripAdvisor Traveler Review Rating Reviewed 2 days ago

I spent 3 days at Round Hill Hotel in Jamaica. Great location, close proximity from Montego Bay airport, but a world to itself. Words cannot describe the beauty of this very special hotel. If you are looking for an elevated and authentic Jamaican experience, Round Hill is your place. From the luxurious elegance of its rooms and villas, to the breathtaking lush gardens, tropical greenery and many beautiful beaches, Round Hill offers a very relaxing environment. Most importantly, the staff was exceptional. From the front desk to the restaurants they were all on point. Can't wait to get back to Round Hill. Roger Lord, Brooklyn, NY.

rogerdlord - Brooklyn, New York


A Caribbean Classic

TripAdvisor Traveler Review Rating Reviewed 1 week ago

We just returned from a really enjoyable 4 night, 5 day trip to Round Hill. The staff, particularly Shelly, Burch, and Owen, were all very pleasant and helpful. The grounds are very well kept and beautiful, with great views of the Caribbean and sunsets. The food was well prepared and the drinks were delicious. We booked a 1 bedroom suite with a plunge pool, but the accommodations were more like a 1 bedroom villa with 3 floors and an amazing full size pool. The top floor consisted of the bedroom, ample closet space, a large full bath, and two large balconies - one overlooking the entrance and one overlooking the pool. The middle floor was the main entrance and living room with a full bath, closet space, and a large balcony overlooking the pool. The bottom floor was another large living space with a dinning table, kitchen, and full bath with an outdoor shower, and opened to the pool area. The entire space has a very open design that we really liked. We would have given Round Hill 5 stars except for one issue that was bothersome. We were told the previous guest took the key with them when they left and there was not an extra key. While we were able to lock the suite/villa while we were in it, (we thought) we were not able to lock it when we left to go to the beach or dinner. The reason I said we “thought” we could lock it while we were in it is because we realized the glass door to the outdoor shower either does not have a lock or we could not find it, and the internal locks we tried to use did not work. So, although we felt safe, there was some discomfort that the suite/villa could not be secured. Hopefully they will get those issues corrected because being able to secure the accommodations, while we are there and when we are out, is a minimum expectation. Other than that issue, we give Round Hill high marks. We had a great time and the people were great.

Brian L


A fabulous experience!

TripAdvisor Traveler Review Rating Reviewed 2 weeks ago

Round Hill was a fantastic experience for my family of four (including two young girls). Or Villa was gorgeous and well maintained, complete with friendly personalized breakfast everyday. The staff was extremely friendly and kind to us at every juncture. Their kids club was also a delight for our girls. While venturing into town or doctors beach works require a driver, the scenery here was so idyllic we didn’t feel the need to venture out save for a trip to the dolphin cove. Between the beach and the infinity pool, we had a fantastic visit and look forward to as future return!

kennys791


Read more reviews or write a review

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


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