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