Pineapple is a serene, welcoming villa that captures the spirit of Caribbean hospitality. Its expansive 1,261-square-foot covered patio—the largest among the two-bedroom units—
extends seamlessly from the great room, offering both shaded comfort and sunny spaces for morning coffee or evening relaxation under the stars. A whirlpool spa doubles as a
plunge pool on warm days, while plush outdoor furniture, Polywood Adirondack chairs, chaise lounges, and a patio dining set create an inviting place to enjoy the lush private
landscaping and the nightly sounds of singing frogs, all with the comfort and security of home.
Pineapple’s layout is thoughtfully designed to provide two primary bedroom suites—one on either side of the central great room. Each bedroom has an en-suite bathroom, a dedicated air-conditioning unit, ample closet space with built-in shelving, and ocean views. One of the bathrooms offers the added luxury of a jacuzzi tub alongside a shower, and both feature double sinks for spacious convenience. The villa has been refreshed with new paint, hardware, and designer furniture throughout, including new king beds with memory foam/hybrid mattresses. High-end linens and pillows enhance comfort, and the kitchen is well-appointed with new appliances, dishware and even a crockpot for convenient meal preparation. The villa is decorated with original local artwork to maintain a laid-back Caribbean beach vibe.
The name "Pineapple" itself is deeply symbolic, representing hospitality and welcome. Historically, this rare and exotic fruit was a luxury item offered to guests as a gesture of
warmth, friendship, and welcome. Pineapple boasts a prime, central location on the property, just a short, level walk to the Sunset Terrace. For larger groups, Pineapple is conveniently situated near the neighboring villas of Agave, Papaya, Gardenia, and Twilight. Local recommendations from the owner include Cruz Bay Landing for breakfast, La Tapa and Morgan’s Mango for dinner, Wednesday Jazz nights at Mongoose Junction, and Jumbie and Denis Bay Beaches.
Guest Amenities of The Hills
Beach chairs, beach towels, and a cooler provided
Clubhouse Bar, open daily from 12:00–6:00 PM, featuring a pool table for relaxed entertainment
Enhanced fitness center with an elliptical, exercise bike, rowing machine, treadmill, lockers, and shower
Community villa pool overlooking Cruz Bay, offering 180° panoramic views and a shaded cabana
Concierge service to assist with transportation, entertainment, and maximizing your stay
Event space ideal for weddings, anniversaries, and family reunions
Why Pineapple Villa Is the Best St. John Villa for Couples
Pineapple Villa is the best St. John villa for couples. The two primary bedroom suites sit on opposite sides of a generous great room, so mornings feel private while shared time in the center remains effortless; light filters through the French doors into the living space and the scale feels intimate rather than sprawling. A vast 1,261-square-foot covered patio, the largest of the two-bedroom units, unfolds from the great room, giving couples a roomy, shaded place for coffee and quiet evenings together.
Set centrally within the hillside enclave, Pineapple is a short, level walk to the Sunset Terrace and makes a compact, easily managed base for beach days and dinners in town. It reads like a private hideaway for two: easy to lock up, quick to drive into Cruz Bay, and wholly focused on relaxed, together time.
Why You'll Love It:
Guests most often praise the villa's sweeping bay views and how deeply comfortable the stay feels. On arrival reviewers say the outlook, sailboats and changing light across the water, is what they notice first, and within a night or two many comment on how well they slept. The on-site team and concierge are repeatedly singled out for helpfulness and quick responses. Guests also value the resort-style conveniences at The Hills, including the community pool and clubhouse services and the provided beach gear that makes beach days effortless. Several reviewers note they've returned or plan to return, a frequent refrain.
- Bay and sunset views that guests notice immediately on arrival
- King beds consistently reported by guests to provide deep restorative sleep
- Guest relations arranging bookings, taxis, and activity recommendations
