Your next vacation should be legendary. And these historic homes-turned-villa rentals the perfect places to do so. Don’t just visit a spectacular destination; visit another era, with striking centuries-old homes combining traditional structure and décor with modern-day luxuries like private pools and gyms. History starts here:

Borgo Finocchieto Estate, Italy 

The Borgo Finocchieto Estate is not just a villa, it’s a village – a restored 800-year-old Tuscan village, to be exact. Stone pathways connect multiple houses (with 22 bedrooms in total) surrounding central living spaces across this sprawling property. Everything inside and out is traditional Tuscany, from the brick arches and wine tasting room to the rolling vineyard-covered hills. 

Chateau Ventoux, France 

In France, history plus luxury equals a vacation in a castle. Chateau Ventoux is an 18th-century estate perfectly restored to replicate its original Provencal design, with warm colors and elegant details. You’ll feel like royalty as you visit with guests in the three reception rooms, dine around a 15-person table, and stroll around the park-like grounds and courtyards.  

Chateau de Normandie, France

Speaking of castles, welcome to Chateau de Normandie, a fantastical 89-acre residence complete with towers and moats. Inside, you’ll find priceless antiques, authentic family portraits, and cozy fireplaces; the outdoors features farmland, a park, and gardens – which you can tour by horseback. Enjoy chef-prepared meals by candlelight in the dining room.  

Fortland’s Point, Jamaica 

A stay here is like an exploration. Fortland’s Point is located on a private peninsula on Discovery Bay, said to be the first stop in Jamaica for Christopher Columbus in 1494. This massive property was later the site of a stone fort. While here, make your own discoveries – of the three private beaches, the cannons dotting the grounds, and the commanding Caribbean views. 

Tiberio, Italy

Tiberio takes it way back – to the 12th century. Set atop a hill in the Umbrian countryside, this former medieval fortress has been completely restored to a welcoming, luxurious house. The historic elements – remarkable stonework, period art, exquisite décor – are still prominent throughout, perfectly complemented by the spacious living areas and fairytale scenery.  

Mullins Mill, Barbados 

This villa is as sweet as it gets. The main house at Mullins Mill is built around a traditional Caribbean sugar mill, a remnant of the island’s booming sugarcane industry in the 17th century. Step back in tropical time with a stay in this airy, garden-surrounded home with stone-framed doorways and classic paintings on the ceilings and walls.   

See all the historic estates in our collection. Or contact us at 800.289.0900 to speak to a qualified villa expert who will help you explore which luxury villa best suits you.