
Avalon
4 Bedrooms
From $1,271 USD - $2,980 USD / nt
From $1,846 USD - $5,082 USD / nt
Overlook Villa is one of the most sought-after Jamaica villas within the exclusive Tryall Club. Perched high on the hillside, this private villa offers sweeping views of the Caribbean Sea, surrounded by lush tropical gardens, towering palms, and vibrant blooms. Guests enjoy easy access—by foot or golf cart—to the Tryall Club’s world-class amenities, making it an ideal choice for luxury villas in Jamaica and Caribbean villa rentals.
5 spacious bedrooms – accommodates up to 10 guests.
Elegant Caribbean-inspired décor with open, breezy living spaces.
Expansive heated infinity pool with jacuzzi platforms and a tranquil fountain.
Nestled in a peaceful hillside setting for total privacy.
Access to Tryall Club’s golf course, tennis courts, spa, and private beach.
Overlook offers the ultimate Jamaica private villa rental experience. Your stay is fully supported by a professional villa team:
Butler.
Private chef.
Housekeeper.
Laundress.
Gardener.
Your chef will craft personalized menus, while your butler arranges daily activities, from tee times to island excursions.
Air-conditioned dining room and outdoor dining under the stars.
Wi-Fi, surround sound, and Starlink-connected SMART TVs with North American channels.
Seamless blend of traditional island charm and modern convenience.
Whether you’re looking for exclusive villas in Jamaica, family villa rentals, or luxury Caribbean villas, Overlook is designed for relaxation and connection. Guests can:
Wake up to refreshing sea breezes.
Spend the day golfing, playing tennis, or lounging poolside.
End the evening with sunset cocktails and an unforgettable dinner.
Families and groups seeking spacious holiday villas to rent in Jamaica.
Travelers wanting beachfront villa access with hillside privacy.
Guests looking for luxury Jamaica vacation villas with dedicated staff.
If you are interested in renting this villa in Jamacia contact us today
Explore More Villas in Jamaica
USA/ Canada: +1 347 707 1195
UK / International : +44 1978 368531
Email: [email protected]
For luxury villas to rent in other areas of the Caribbean visit: www.worldwidedreamvillas.com
From | To | Min Stay | Nightly Rate | Weekly Rate |
---|---|---|---|---|
22-Nov-2025 | 28-Aug-2025 | 7 | $3,087 USD | $21,615 USD |
18-Aug-2025 | 31-Oct-2025 | 7 | $1,846 USD | $12,925 USD |
01-Nov-2025 | 21-Nov-2025 | 7 | $2,149 USD | $15,046 USD |
29-Nov-2025 | 12-Dec-2025 | 7 | $2,149 USD | $15,046 USD |
13-Dec-2025 | 19-Dec-2025 | 7 | $3,865 USD | $27,060 USD |
20-Dec-2025 | 02-Jan-2026 | 7 | $4,557 USD | $31,900 USD |
04-Jan-2026 | 06-Mar-2026 | 7 | $3,396 USD | $23,777 USD |
07-Mar-2026 | 27-Mar-2026 | 7 | $3,396 USD | $23,777 USD |
28-Mar-2026 | 24-Apr-2026 | 7 | $3,396 USD | $23,777 USD |
25-Apr-2026 | 24-Jul-2026 | 7 | $2,231 USD | $15,620 USD |
25-Jul-2026 | 30-Oct-2026 | 7 | $2,031 USD | $14,218 USD |
31-Oct-2026 | 20-Nov-2026 | 7 | $2,231 USD | $15,620 USD |
21-Nov-2026 | 28-Nov-2026 | 7 | $3,993 USD | $27,951 USD |
28-Nov-2026 | 11-Dec-2026 | 7 | $2,231 USD | $15,620 USD |
12-Dec-2026 | 18-Dec-2026 | 7 | $3,630 USD | $25,410 USD |
19-Dec-2026 | 02-Jan-2027 | 7 | $5,082 USD | $35,574 USD |
From | To | Min Stay | Nightly Rate | Weekly Rate |
---|---|---|---|---|
18-Aug-2025 | 31-Oct-2025 | 7 | $1,857 USD | $13,000 USD |
01-Nov-2025 | 21-Nov-2025 | 7 | $2,028 USD | $14,200 USD |
22-Nov-2025 | 28-Nov-2025 | 7 | $3,630 USD | $25,410 USD |
29-Nov-2025 | 12-Dec-2025 | 7 | $2,028 USD | $14,200 USD |
13-Dec-2025 | 19-Dec-2025 | 7 | $3,300 USD | $23,100 USD |
20-Dec-2025 | 02-Jan-2026 | 7 | $4,620 USD | $32,340 USD |
04-Jan-2026 | 06-Mar-2026 | 7 | $3,630 USD | $25,410 USD |
07-Mar-2026 | 27-Mar-2026 | 7 | $3,993 USD | $27,951 USD |
28-Mar-2026 | 24-Apr-2026 | 7 | $3,630 USD | $25,410 USD |
25-Apr-2026 | 24-Jul-2026 | 7 | $2,364 USD | $16,551 USD |
25-Jul-2026 | 30-Oct-2026 | 7 | $2,042 USD | $14,300 USD |
31-Oct-2026 | 20-Nov-2026 | 7 | $2,364 USD | $16,551 USD |
21-Nov-2026 | 28-Nov-2026 | 7 | $3,993 USD | $27,951 USD |
28-Nov-2026 | 11-Dec-2026 | 7 | $2,364 USD | $16,551 USD |
12-Dec-2026 | 18-Dec-2026 | 7 | $4,252 USD | $29,766 USD |
19-Dec-2026 | 02-Jan-2027 | 7 | $5,082 USD | $35,574 USD |
Rental rates are subject to 10.00 % TAX plus 7.50 % service charge.
USA/CANADA: +1 347 707 1195
UK /International : +44 1978 368531
Barbados: +1 246-432-6307
Email : [email protected]
UK: 40 Knutsford Road, Alderley Edge, Cheshire SK9 7SF
Barbados: Indigo Courtyard, Holetown, Barbados Bb24917
A great way to communicate as we can answer your questions in real time. We are usually available 6 days a week between 9am and 8pm.