Soak up Tuscany’s rose-hued ambience at Villa Gaia, a restored 15th-century villa that once sheltered noble families. This destination comes with on-site staff ready to indulge your every whim. Enjoy private tennis, swimming, bocce, and mountain biking, or explore nearby woodland paths. Located in the tiny village of Casole d’Elsa, the villa offers guests a glimpse into yesteryear without compromising on modern amenities. With 18 bedrooms, it’s an experience meant to be shared! Rentals from $8,610 per night.