Fiddler's Green Villa — 5-Bedroom Hilltop Estate Above Simpson Bay
A luxury 5-bedroom villa with private pool and panoramic ocean-lagoon views, perched in the Simpson Bay hills for up to 10 guests.
Why Go
Fiddler's Green Villa is the kind of property that earns its price tag with the view alone — panoramic ocean and lagoon vistas from a hilltop position above Simpson Bay, with five bedrooms, a private pool, and enough space for ten guests to spread out without getting in each other's way.
The Experience
The Simpson Bay hills are where the island's premium villa stock concentrates, and Fiddler's Green occupies one of the better positions in this elevated neighborhood. From the hillside at 8 Limpet Road, the views sweep from the Simpson Bay lagoon on one side to the open Caribbean Sea on the other — a dual panorama that changes character throughout the day as the light shifts. The villa itself is built for groups: five bedrooms, multiple terraces, a modern kitchen equipped for serious cooking, and a private pool that sits at the center of the outdoor living space. The contemporary Caribbean design balances indoor and outdoor areas, with living spaces that open onto terraces and the lush tropical landscaping that gives the property its green, secluded feel. Down the hill, Simpson Bay offers everything the villa does not — restaurants, marinas, casinos, beach bars, and the Simpson Bay Bridge that opens twice daily for sailboats. The contrast between the hilltop serenity and the bay-level energy is part of the experience. You come back up the hill in the evening, pour something cold, and watch the lagoon turn orange while the noise stays below.
What to Try
Cook a group dinner using the fully equipped kitchen and eat on the terrace with the panoramic view — this is what the villa was designed for. Drive five minutes to Simpson Bay Beach for morning swimming. Walk the marina strip for restaurant options ranging from Italian to sushi to Caribbean barbecue. Take a boat charter from Captain Alan's for a day trip to Anguilla or Prickly Pear. Watch the Simpson Bay Bridge opening at 9:30 AM and 5:30 PM — the parade of sailboats is a daily show.
Insider Tip
The Simpson Bay hilltop catches trade winds that the bay-level properties miss entirely. On hot days, the villa's elevation means you can often skip the air conditioning during the afternoon — open the terraces and let the breeze do the work.
The Practical Stuff
Located at 8 Limpet Road, Simpson Bay hills, Dutch side. 5 bedrooms, sleeps up to 10 guests. Private pool, multiple terraces, full kitchen, AC throughout. Price range: luxury ($$$). Simpson Bay Beach is 5 minutes downhill. Princess Juliana Airport is 10 minutes away. A car is essential for the hilltop location. The road up is steep but paved.
Pair It With
- CAPTAIN ALAN'S BOAT CHARTERS Guide — Day trip boat charters departing from Simpson Bay marina
- Big Fish Seafood Grill Guide — Fresh seafood restaurant for nights when no one wants to cook