An 8-foot aquarium divides the lounge and media room at this entertainer’s dream a short drive from Paynes Bay Beach. The sprawling and secluded terrace is home to an oversized infinity pool, hot tub, water features, a covered wet bar, and alfresco dining with barbecue. All bedrooms boast en suites, while the master also has a jacuzzi tub and plasma TV. At Stanford House, you’re close to Holetown’s shopping and nightlife.

Summer price: US $1,500 per night
Winter price: US $2,500 per night
Christmas price: US $4,000 per night