Jamaica Inn, Jamaica
Wow factors: With their rambling verandas, private infinity pools, spacious outdoor showers, and charming blue-and-white, Victorian-inspired bedrooms with four-poster beds, Cottages 3 and 4 feel nothing like resort accommodations. Rather, they feel more like swanky, personalized beach houses with the amenities of a fine hotel. The cottages are located on a bluff overlooking the Caribbean, in Ocho Rios. Our favorite part: Each has a private entrance to the sea.
When you do leave the room: The resort offers all the beach activities you could want, plus polo, golf, and a long list of excursions like biking or river rafting.
Rates: From $812 per night, other rooms from $299 per nightCourtesy of Jamaica Inn