Sonoma County, California
With four bedrooms, an expansive pool, an outdoor shower, a boccie court, a croquet lawn, and its own vineyards, Villa Nel Bosco is an ideal base from which to enjoy the Napa Valley’s fall crush. Inside the two-story residence, antiques and art commissioned specifically for the home mix with rich leather sofas and plush beds for a cozy retreat. Nightly rates start from $1,350.
Beautiful Places, 800.495.9961, www.beautiful-places.com
Located on the second floor of an eight-unit palazzo in central Florence originally built by Filippo Brunelleschi in 1420, the 3,400-square-foot Camerata apartment offers three bedrooms and was last renovated in 2012. The 18th-century frescoes remain, while modern updates include a contemporary kitchen, flat-screen TVs, and luxurious bathrooms. Nightly rates start at $1,250.
Time and Place, 866.605.3542, www.timeandplace.com
Providenciales, Turks and Caicos
The 6,430-square-foot penthouse at the Villas at Grace Bay includes four bedrooms, a media room, and a private 2,630-square-foot rooftop terrace that spans 130 feet of ocean frontage and holds two Jacuzzis. A tasty time to visit is from October 31 through November 2, when the Grace Bay Club will help host the third annual Caribbean Food & Wine Festival, which will include chefs Christina Tosi (Momofuku Milk Bar) and Top Chef’s Tiffany Derry. Nightly rates for the Grace Bay Penthouse Suite start at $4,560.
Grace Bay Club, 800.946.5757, www.gracebayresorts.com