Set on Hamilton Harbor and surrounded by lush greenery, this landmark property has gotten a major upgrade. Read Indagare's review of the Hamilton Princess.

This 26-acre-island reserve, just a short boat ride from Hamilton, has a full-service villa (including a dedicated chef and water sports instructor available upon request). The main villa sleeps eight in a two-bedroom master suite and two one-bedrooms that are modern in feel, with contemporary décor and a sand and white color scheme. Bathrooms have deep soaking tubs and rain showers; there are also two outdoor showers. The Guard House is a bit more no-frills and can accommodate eight more (two in one bedroom and six in a tight bunkroom) for a total of 16 guests, though 10 to 12 would be preferable. (This would work best for kids over eight, traveling with a nanny/babysitter or a family). Be advised that there are steep ladders leading to loft areas for rainy day reading or hanging out in the main house. The Guard House also has a hot tub on the viewing deck upstairs. There is a private dock and a small beach and terrace. A pool and outdoor entertaining spaces are being added to the property. The island was once a Boer War prison camp from 1901-2, holding 1,300 prisoners. Though the property on-site is still a work-in-progress, it's an unusual option for anyone looking for a private island escape from New York in just a few hours.

The Rosewood Bermuda is the island's top luxury hotel, and also the youngest. While other hotels on the island brag of century-old history, the Rosewood was only constructed in 2009, which means better infrastructure with contemporary aesthetics (in keeping with a British colonial style) and modern facilities.

Bermuda's beachfront The Loren is a Bermudan oasis and a stylish and sophisticated retreat for couples. Read Indagare's review.

This modern seven-bedroom house has 13 bathrooms (eight are en suite and sizable, like the dressing room-size closets). The Residence sleeps up to 16 people, making it perfect for a long weekend house party, a special celebration or a week away with family or friends. (The Loren is a popular location for weddings.) There are two kitchens and terraces (the second also has a bar and grill area for entertaining poolside), plus a fitness room, a pool and a media room. Most of the bedrooms are doubles and have balconies facing the ocean, so that almost every room has a view of the sea, even from bed. The master has a large terrace with a view and the bedroom next to the master, a view from the shower. The house also sits on its own private beach and comes with butler service and a private chef. Room service is also available and the on-site butler can arrange for a deejay, yoga instructor or even a private concert by a local singer.

The design vibe at The Residence is cool-contemporary, with natural-wood floors, soft greige tones with hints of color. Though the house itself looks a bit like a white concrete bunker from a distance, windows everywhere optimize the views. While you won't find king beds in every room, rollaways are available upon request. There's plenty of time for lounging by the pool or enjoying poolside massages are a perfect way to cap off an afternoon.