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From $2,354 USD - $8,324 USD / nt

Following Seas

Montego Bay  Jamaica
6
6
From $2,354 USD - $8,324 USD / nt
From $2,354 USD - $8,324 USD / nt
We love this villa because...
its breathtaking hilltop ocean views, elegant indoor-outdoor living, full staff, and the unmatched privacy it offers within Tryall Club.

Following Seas – A Private Hilltop Luxury Villa in Jamaica

Set high on one of the most scenic peaks of the renowned Tryall Club, Following Seas is a magnificent example of elegant Jamaica villa rentals. This spacious private estate covers seven acres of landscaped tropical gardens and blends traditional Caribbean charm with modern luxury.

With spectacular views of the Caribbean Sea, lush mountain surroundings, and impeccable design, Following Seas offers guests a serene escape with the feel of a well-loved family retreat.


A Serene and Stylish Caribbean Retreat

This beautifully styled Caribbean villa brings the outdoors in with its seamless flow between interior and exterior living spaces. Whether you're planning a quiet retreat or a vibrant gathering, the villa is designed to accommodate both with ease.

Highlights include:

  • Expansive indoor living and dining areas with elegant décor.

  • Covered terrace overlooking an infinity-edge pool and the ocean.

  • Secluded Jacuzzi and sun deck for complete relaxation.

  • Open-air gazebo dining area that seats up to 35 guests.

  • Separate media cottage with bar, 80-inch TV, and sunset views.

  • Cantilevered viewing deck offering lush rainforest vistas.


Luxurious Bedroom Suites for Flexible Stays

Following Seas is available to rent as a 4, 5, or 6-bedroom Jamaica villa, offering the flexibility to suit both smaller groups and larger families.

The Main Villa features:

  • Four spacious bedrooms, each with an en-suite bathroom and flat-screen TV.

  • A primary suite with dual bathrooms, a private dressing area, and an outdoor shower.

The Guest Cottage includes:

  • Two additional bedrooms.

  • A shared living area.

  • Private plunge pool and terrace.

  • Ideal for guests seeking added privacy within this Jamaica private villa.


Premium Amenities & Five-Star Service

This luxury villa in Jamaica ensures comfort and convenience at every turn:

  • Tower gym with panoramic 360-degree views.

  • Four golf carts for exploring the expansive Tryall Club grounds.

  • Dedicated staff of seven, including a chef, butler, housekeepers, and more.

  • Concierge service available to arrange in-villa spa treatments, excursions, and more.

This is more than just a vacation—it’s a fully immersive Caribbean villa experience.


Ideal for Families, Groups & Luxury Travelers

Whether you're planning a multigenerational getaway, a romantic retreat, or a celebration, Following Seas is among the top exclusive villas in Jamaica for:

  • Jamaica family villa rentals.

  • Luxury holiday villas to rent in Jamaica.

  • Jamaica villas with pool and staff.

  • Beachfront-style villas in Jamaica (elevated ocean views).

  • Private villa rentals in Jamaica offering full privacy and personalized service.


Looking for More Villas in the Caribbean?

In addition to Jamaica luxury villas, Caribbean Dream Villas offers a curated selection of premium vacation villas in the Caribbean, including top-rated Barbados villas for rent, St. Barts estates, and other Caribbean luxury villas to rent.


Enquire Now for Your Jamaica Dream Vacation

Don’t miss the opportunity to stay at Following Seas, one of the most exclusive vacation villas in Jamaica. With its stunning setting, thoughtful design, and attentive staff, it’s a villa that guests return to time and again.

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

See more details...

Looking for Jamaica Villas to Rent?

Looking for Jamaica Villas to Rent?Caribbean Dream Villas, a trusted Caribbean villa specialist and part of Worldwide Dream Villas, offers a handpicked selection of luxury villas to rent in Jamaica. Whether you’re seeking a beachfront villa, a private pool retreat, or a family-friendly holiday home near Jamaica’s top attractions, we provide some of the finest Jamaica villa rentals available. Explore villas to rent in popular areas like Montego Bay, Negril, and Ocho Rios. With stunning ocean views, professional concierge services, and easy access to Jamaica’s best beaches, dining, and golf courses, our villas for rent in Jamaica are ideal for couples, families, and groups looking for a memorable Caribbean vacation. Book your perfect Jamaica villa getaway with Caribbean Dream Villas today!

Rate

From To Min Stay Nightly Rate Weekly Rate
13-Dec-2025 19-Dec-2025 7 $5,012 USD $35,090 USD
19-Dec-2026 02-Jan-2026 7 $8,324 USD $58,274 USD
20-Dec-2025 02-Jan-2026 7 $7,432 USD $52,030 USD
04-Jan-2026 06-Mar-2026 7 $5,363 USD $37,546 USD
07-Mar-2026 27-Mar-2026 7 $6,065 USD $42,459 USD
28-Mar-2026 24-Apr-2026 7 $5,363 USD $37,546 USD
25-Apr-2026 24-Jul-2026 7 $2,808 USD $19,658 USD
25-Jul-2026 30-Oct-2026 7 $2,354 USD $16,480 USD
31-Oct-2026 20-Nov-2026 7 $2,808 USD $19,658 USD
21-Nov-2026 28-Nov-2026 7 $6,065 USD $42,459 USD
28-Nov-2026 11-Dec-2026 7 $2,808 USD $19,658 USD
12-Dec-2026 18-Dec-2026 7 $5,363 USD $37,547 USD
19-Dec-2026 02-Jan-2027 7 $8,324 USD $58,274 USD
From To Min Stay Nightly Rate Weekly Rate
13-Dec-2025 19-Dec-2025 7 $5,012 USD $35,090 USD
20-Dec-2025 02-Jan-2026 7 $7,432 USD $52,030 USD
04-Jan-2026 06-Mar-2026 7 $5,363 USD $37,546 USD
07-Mar-2026 27-Mar-2026 7 $6,065 USD $42,459 USD
28-Mar-2026 24-Apr-2026 7 $5,363 USD $37,546 USD
25-Apr-2026 24-Jul-2026 7 $3,544 USD $24,813 USD
25-Jul-2026 30-Oct-2026 7 $3,036 USD $21,527 USD
31-Oct-2026 20-Nov-2026 7 $3,544 USD $24,813 USD
21-Nov-2026 28-Nov-2026 7 $6,065 USD $42,459 USD
28-Nov-2026 11-Dec-2026 7 $3,543 USD $24,801 USD
12-Dec-2026 18-Dec-2026 7 $5,363 USD $37,546 USD
19-Dec-2026 02-Jan-2027 7 $8,324 USD $58,274 USD
From To Min Stay Nightly Rate Weekly Rate
13-Dec-2025 19-Dec-2025 7 $5,012 USD $35,090 USD
20-Dec-2025 02-Jan-2026 7 $7,432 USD $52,030 USD
04-Jan-2026 06-Mar-2026 7 $5,363 USD $37,546 USD
07-Mar-2026 27-Mar-2026 7 $6,065 USD $42,459 USD
28-Mar-2026 24-Apr-2026 7 $5,363 USD $37,546 USD
25-Apr-2026 24-Jul-2026 7 $3,952 USD $27,668 USD
25-Jul-2026 30-Oct-2026 7 $3,399 USD $23,793 USD
31-Oct-2026 20-Nov-2026 7 $3,952 USD $27,668 USD
21-Nov-2026 28-Nov-2026 7 $6,065 USD $42,459 USD
28-Nov-2026 11-Dec-2026 7 $3,952 USD $27,668 USD
12-Dec-2026 18-Dec-2026 7 $5,363 USD $37,546 USD
19-Dec-2026 02-Jan-2027 7 $8,324 USD $58,274 USD

Plan Your Trip

Amenities

  • Air Conditioned bedrooms
  • Ceiling Fans
  • Communal Facilities
  • Golf Cart
  • Golf Resort
  • Gym/Fitness Room
  • Outdoor Jacuzzi
  • Plunge Pool
  • Private Garden
  • Private Pool
  • Restaurant
  • Shop
  • Sound System
  • Staffed Villa
  • TV
Bedroom : 6
Bathroom : 6

Staff

  • Butler
  • Chef
  • Gardener
  • House keeper
  • Laundress

HAVE QUESTIONS?

USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK / INTERNATIONAL: +44 1978 368531

Location

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Get In Touch

CONTACT US

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

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