Originally built in the 11th century, this nine-bedroom, eleven-bathroom castle has all the makings of a fantasy. In addition to its inside opulence, the estate's spacious grounds and party areas are sure to wow. Hike the paths through the countryside of Grosseto before taking a cooking lesson in the kitchen's stone arches or enjoying a drift hunters wine tasting on the roof as the sun sets. You may not want to leave once you see the infinity pools, gazebo, and spacious grounds. However, Siena, Italy's top sights are just a 75-minute drive away.

Near Southampton Village and the ocean, this four-bedroom, three-and-a-half-bathroom Hamptons house is ideal for summer vacations away from the city. There is a gas fireplace, a chef's kitchen, a pool, a barbecue, and lots of outside space with sun loungers and tables under umbrellas.

This beautiful property in the wine region has a Zen garden with a babbling fountain and sun loungers. The three-bedroom, three-bathroom house in the magical garden comes with all the standard features, including a kitchen, a gaming room, a fireplace, and more. Outdoor amenities such as a swimming pool, hot tub, terrace dining, BBQ grill, and views of Mount Tamalpais and the Sonoma Valley are the true appeal, however.

There are many stunning properties in Palm Springs, but none quite like the four-bedroom, six-and-a-half-bath mansion that Frank Sinatra had built especially for him in 1947. There are some nice nods to traditional mid-century architecture, and the piano-shaped pool is great for hot summer days.

This eight-bedroom, nine-and-a-half-bath beachfront property on South Carolina's Hilton Head Island offers a luxurious resort experience. Guests may enjoy the five-star services in complete seclusion by making use of the outdoor facilities, which include a pool with a swim-up bar, a fire pit, a tiki bar, a hot tub, and more.

This sleek and sophisticated Nantucket house sleeps 12 in its six bedrooms and six and a half baths. The pool, hot tub, fire pit, and grill are all necessary summer amenities, and the sea-inspired design creates a traditional New England vibe. The villa is conveniently located close to local amenities including shops, restaurants, and the beach.