Endless Summer Escape
Elegant five-bedroom hillside retreat at Round HillI Estate featuring panoramic Caribbean Sea views I private location minutes from Montego Bay.
Perched high on the hillside within the iconic Round Hill Estate, Hillside House captures the timeless elegance of Old Jamaica while offering the comfort and style of modern luxury. Long admired as one of the estate’s most striking villas, this exceptional retreat is known for its sweeping panoramic views and refreshing trade winds that flow naturally through the property. Designed with families and groups in mind, Hillside House delivers a relaxed yet refined island experience — a welcoming sanctuary where guests can truly unwind and enjoy the beauty of Jamaica.
For more than sixty years, Round Hill Estate has attracted royalty, world leaders, and music legends, earning its reputation as one of the Caribbean’s most distinguished destinations. Hillside House enjoys a privileged and private setting on the eastern side of the hill, offering seclusion while remaining just minutes from the resort’s renowned amenities. The villa is also conveniently located less than thirty minutes from Sangster International Airport and the vibrant town of Montego Bay.
The villa’s Great Room opens seamlessly onto its most spectacular feature — a spacious, beautifully furnished verandah balcony overlooking an extraordinary ten-mile stretch of the Caribbean Sea. From this vantage point, guests can take in uninterrupted views all the way to the distant shoreline of Montego Bay. As evening falls, the twinkling lights of the city shimmer across the water, creating a magical backdrop for candlelit dinners or relaxed cocktails on the balcony. Gentle trade winds and unforgettable views invite guests to linger long into the evening before retreating to their private suites.
Hillside House features five well-appointed bedrooms, each thoughtfully designed for comfort and privacy. Every bedroom includes quiet remote-controlled air conditioning, ceiling fans, in-room safes, cable television, and an en-suite bathroom with a walk-in shower.
Four of the bedrooms open to spectacular views across the bay, capturing both the shimmering Caribbean Sea and the distant lights of Montego Bay. The fifth bedroom enjoys a peaceful outlook onto a small private tropical garden, offering a serene and secluded retreat within the villa.
Round Hill Membership : Round Hill offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar, and unforgettable long sunsets from the waterfront terrace. Guests receive complimentary use of the Round Hill gym; the $25 daily fee is waived for Hillside House guests (paid for by the homeowner). Hillside House guests also receive complimentary WiFi throughout Round Hill (daily fee waived/paid by the homeowner). For additional charges, members may enjoy the spa, tennis courts, afternoon tea, and Wednesday Manager's Cocktail Party, Pineapple Kids Club, fitness center, salon, a range of water sports, and beach parties.
Tryall Club Membership : The Tryall Club membership: complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, new Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night
Please note: Round Hill and The Tryall Club membership is guaranteed for guests traveling through November 1, 2026.
Bedroom 1: Master bedroom with a king-size bed, ceiling fan, A/C, WiFi, access to the pool terrace and en-suite bathroom with bathtub, walk-in shower, double vanity and WC. 2 guests maximum.
Bedroom 2: Master bedroom with a king-size bed, ceiling fan, A/C, WiFi, access to the pool terrace and en-suite bathroom with bathtub, walk-in shower, double vanity and WC. 2 guests maximum.
Bedroom 3: Bedroom with a queen-size bed, ceiling fan, A/C, WiFi, sea view and en-suite bathroom with walk-in shower, vanity and WC. 2 guests maximum.
Bedroom 4: Bedroom with two single beds (can be made as a king size bed), ceiling fan, A/C, WiFi, sea view and en-suite bathroom with walk-in shower, vanity and WC. 2 guests maximum. This bedroom connects to Bedroom 5 for a convenient parent-child suite if desired.
Bedroom 5: Bedroom with two single beds (can be made as a king size bed), ceiling fan, A/C, WiFi, and en-suite bathroom with walk-in shower, vanity and WC. 2 guests maximum. Optional connection to Bedroom 4 via the private garden for a convenient parent-child suite.
Interior Access Bedrooms: 5
Once a vacation home is selected, the pampered adventure begins. Our concierge team will assist with creating a magical and immersive vacation experience. Our services include
While available for advanced requests, the concierge team connects with guests 30 days prior to arrival to coordinate arrivals and to reserve desired services and experiences. Guests with scheduled Christmas/New Year stays will be contacted 90 days prior to arrival.
Earn up to a US$500 concierge credit on qualifying bookings
The Endless Summer Escape applies to all new reservations booked between May 12 and August 31, 2026.
Terms and conditions
Credit is based on total booking value before taxes and fees. Credit applies to experiences only and cannot be used toward villa rental, taxes, or fees. Credit must be used during the booked stay and expires at checkout. Cannot be combined with other offers and has no cash value. Valid only on new reservations made within the booking window. Concierge service must be booked directly through our website and does not apply to third-party providers or external websites.
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