Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
Inquire for Rates
Milestone Cottage
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Milestone Cottage has always been the honeymoon favorite, although also popular for small families with its two bedrooms. Built many years earlier, it was purchased in 1986 and extensively remodeled and personalized. This is when its luxurious cliff-side ... more
$1,365 - $1,774 /night
Peeniwalli
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Pure and uniform, Peeniwalli’s white and neutral-toned appearance balances against a spellbinding backdrop of blue sky, rolling sea and lush vegetation. The colors come from living. It’s in the furniture and people, nature and the outdoors, rather tha... more
$1,357 - $4,571 /night
Vista del Mar
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$1,357 - $3,715 /night
Allamanda
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
A special amenity available to guests in this villa is its complimentary membership with The Tryall Club. This membership enhances your stay with exclusive access to The Tryall Club's prestigious amenities and services. Enjoy a wealth of luxurious... more
$1,357 - $4,436 /night
Endless Summer
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Endless Summer is a turreted mansion with views of the Caribbean Sea. From the porte-cochere, bevelled glass doors open to a dramatic 80-foot columned space. A sweeping white stone staircase curves gracefully from the foyer to a balustrade gallery encircl... more
$1,322 - $3,857 /night
Tranquility on the Beach
7 Bedroom Villa, 6 Bathrooms, Sleeps 14
True to its name, Tranquillity is a place for relaxing into the calm ambiance of an exquisite home on a waterfront site while being gently pampered by a competent staff.
The well-appointed rooms of Tranquility stretch over 6,300 square feet of rich mar... more
$1,271 - $2,981 /night
Avalon
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$1,242 - $1,815 /night
Seven Seas
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Designated a protected coconut plantation, the three-acre grounds are dotted with 200 healthy coconut palms. Beds are piled high with plump pillows and duvets. Euro-chic bathrooms are immaculate. The outdoor Jacuzzi is bubbling, and the long pool will be ... more
$1,214 - $3,057 /night
Retreat Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$1,207 - $1,569 /night
Steppa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
A simple tropical modern design on a dramatic beachfront landscape, Steppa offers mountain to sea views at every turn. Sculpted white staircases and rounded curved walls allow cool ocean breezes to course through the villa’s indoor and outdoor spaces. J... more
$1,200 - $2,300 /night
Somewhere
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Somewhere Villa is nestled in Prospect Estate's lush tropical garden overlooking the crystal clear waters of the Caribbean sea.
This spacious four bedroom, four bath villa is equipped with modern conveniences such as satellite TV, VCR, telephone and s... more
$1,199 - $1,999 /night
Palm Villa
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Live the luxe life with a private swimming pool and covered outdoor living space at our Palm Villa.
This two-story oceanfront villa features five bedrooms with king beds, en-suite bathrooms, private verandas, a fully equipped kitchen, living room, din... more