Private Islands & Luxury Villas in Bermuda

Tucked away in a sleepy archipelago known as Paradise Lakes, Hawkins Island might be a stone’s throw from Hamilton Harbour, but it’s also a world away from most everything else. After all, this pristine private island features two über-luxurious estate homes that sleep 16 guests total, with not a neighbour or another structure in sight. In fact, you’ll have the entire 25-acre island to yourself making this one of Bermuda’s most sought after vacation rental properties for those seeking a secluded stay like none other. “Hawkins is an ultra-lux piece of the market where you’ll also have an added layer of security since you’re not coming into contact with the general public,” says owner Will Cox. “Plus, you’ve got all the amenities that go with renting a private island.” That means a dedicated team catering to your every need, a personal chef cooking all of your meals, water sports equipment including kayaks, paddleboards and a small sailboat, plus unlimited water taxi transfers to and from Hamilton if exploring the mainland is on your agenda. You’ll also be staying in one of Bermuda’s most luxurious homes with jacuzzi tubs, outdoor showers and spacious water view balconies galore. Says Cox: “It’s really one of the most special places in Bermuda.

Located in tranquil Smith’s Sound between St. David’s and Smith’s Islands on Bermuda’s far east end, Oswego Island is a secluded 3.2-acre sanctuary replete with natural beauty. “It’s an incredibly romantic existence out there,” says owner Rick Spurling who along with his partners Geoffrey and Douglas Redmond acquired Oswego from an eccentric Englishmen in the early 2000’s. At the time the island had a singular ramshackle cottage built in the 1800’s, but once this trio of St. David’s islanders took the reins, they built a glistening new three-bedroom, three-bathroom home that paid homage to Bermudian design without forgoing modern amenities. “It’s a place where you can sit quietly and let history speak to you,” says Spurling who spends most of his time as the director of the St. David’s Historical Society and who’s still moved by Oswego’s ocean views. “From the front patio of the house you look out at a very historic bay and the old channel leading into the harbour,” says Spurling. “It’s the same view that you would’ve had 400 years ago.” In addition to sliding floor-to-ceiling glass walls that convert the inside space to an airy outdoor living area, the house also boasts amenities not seen at other properties—like a 23-foot power boat available to all guests. “If you’re on an island,” says Spurling, “you’ve gotta have a boat.”

When the Loren at Pink Beach first opened its doors in 2017, the chic boutique hotel quickly became Bermuda’s most stylish property with its sexy, ultra-modern décor and to-die-for beachfront location. About a year later the resort unveiled The Residence at The Loren —a sprawling 10,700-sqare-foot mansion sitting on 5.5 acres of waterfront property with six bedrooms, eight en-suite bathrooms, a two-bedroom staff cottage, and high-end amenities like a covered bar, outdoor chef’s kitchen and poolside verandas with ocean views. In short, the Residence is one of Bermuda’s most prestigious properties, which is why Hollywood celebrities, professional athletes and computer tech magnates have all stayed on the premises. “During the high season you're looking at $15,000 a night, so we’re definitely attracting a niche market,” says The Loren general manager, Sebastien Maingourd.

“But you get what you pay for—there’s nothing in Bermuda that can match this level of privacy and amenities.” That means you’ll also have a private 300-foot-long pink sand beach, high-tech fitness center, screening room, tennis court and an oceanfront heated pool where you and your entourage can relax in secluded style. Pair that with a ten-minute drive to Bermuda’s private jet tarmac and you’ve got a recipe for ultimate island luxury.