Milestone Cottage — 2-Bedroom All-Inclusive Cliffside Villa, Jamaica

About Milestone Cottage

Milestone Cottage is the most intimate villa at Bluefields Bay — perched on a low cliff above the Caribbean, with two bedrooms and the kind of seclusion that has made it a longstanding honeymoon favorite. The villa’s defining feature is a cliffside plunge pool with built-in underwater seats, set at the edge of the property where the lawn meets the rock.

A private seaside pavilion above offers a quiet vantage point for sunsets and shaded afternoons. Following a recent renovation, Milestone now operates largely off-grid via dedicated solar power — a quietly distinctive feature for a villa designed for guests who want the rest of the world to recede for a week. Two bedrooms accommodate up to four guests, though most stays are couples and the cottage is sized for that.

A Cliffside Plunge Pool Unlike Any Other

The plunge pool at Milestone Cottage is the property’s most photographed feature, and for good reason. Set at the edge of the low cliff overlooking the Caribbean, it includes built-in underwater seats — a design that lets guests sit submerged to mid-chest with the bay opening out beyond.

In the late afternoon, the underwater seats catch the angled light through the water; in the early morning, the surface holds the bay’s color before the day fully begins. Above the pool, a private seaside pavilion provides a covered, quietly furnished spot for breakfast, sunset drinks, or an afternoon reading.

Bedrooms & Accommodation

Milestone Cottage’s two bedrooms accommodate up to four guests. The master bedroom faces the sea with windows positioned for sunrise; the second bedroom is smaller and works for a child, a guest, or a partner traveling separately. Each bedroom has its own en-suite arrangement.

The living room opens directly onto the grassy lawns and sea views — a continuity between interior and exterior that suits the cottage’s intimate scale. For couples traveling alone, only one bedroom needs to be in use, and the rest of the cottage operates as one expanded living space.

Villa Features & Highlights

Beyond the cliffside plunge pool and seaside pavilion, Milestone’s most distinctive feature is its operational independence: following a post-hurricane renovation that included a redesigned roofline, the cottage was fitted with a full off-grid solar electrical installation. Milestone now runs largely independently of the local grid — a quietly distinctive feature for guests for whom that detail matters.

The roof itself was reshaped during the renovation to optimize solar capture and to be more storm-resilient, both of which serve the broader principle of building for the long term on Jamaica’s South Coast. The grassy lawns extending from the living room toward the cliff edge are tended carefully; many guests describe afternoons spent moving between the lawn, the pavilion, and the plunge pool as the most restorative single feature of a Bluefields Bay stay.

All-Inclusive: What’s Included

Milestone Cottage stays are fully all-inclusive: dedicated private team (chef, butler, housekeeper, concierge, waterfront attendant, night caretaker, 24-hour security), three made-to-order meals daily, unlimited beverages and snacks, laundry, non-motorized watersports, tennis, Club MoBay VIP airport services, and all government taxes. For honeymooners and couples, meals are commonly served on the seaside pavilion or the lawn above the plunge pool — the team adapts without prompting to the rhythm guests set. Nanny service is available on request. Spa, motorized watersports, scuba, and off-property excursions are at additional cost. See full inclusions at our What’s Included page.

Perfect For: Honeymooners & Couples Who Want to Disappear for a Week

The cliffside plunge pool, the seaside pavilion, the intimate scale, and the kind of seclusion that comes from being slightly apart on the property all speak to a clear use case: honeymoons, anniversaries, romantic retreats, and the occasional small family that wants the most contained version of a Bluefields Bay stay.

For couples wanting more nature immersion, Cottonwood Cottage is the alternative; for those who’d accept slightly more communal scale in exchange for adults-only proximity to The Treehouse, the Suites are the alternative. See our couples page for more.

Frequently Asked Questions