This post was produced in partnership with N2S Italia.
With its storied history, manicured countryside, charming towns and legendary vineyards, Tuscany captures the essence of Italian living. And the best way to experience the region, and enjoy “il dolce far niente”, is to stay in a luxurious villa in the Tuscan countryside. It would take a lifetime to explore everything Italy has to offer, but when you book an extended stay in one of our favorite luxury villas in Tuscany, you’ll have the time and space to savor your surroundings and immerse yourself in daily life.
We asked our friends Tommaso and Letizia of N2S Italia, a luxury travel company that embraces slow travel, for a peek inside their portfolio of luxury villas in Tuscany. Thanks to their excellent taste and a passion for sharing real, inaccessible people and places, they’ve curated an exclusive list of unique, private properties available to rent up and down the boot. Each one promises to delight visitors with its history, design, high-level of service and strategic location across the Tuscan countryside.
A Country Estate A Stone’s Throw From Florence
The details: Only a 20-minute drive from Florence, this beautiful Renaissance villa is the perfect base to explore the city while soaking in the countryside. You can even see Brunelleschi’s dome and Giotto’s campanile from the gardens! The large estate features a tennis court, soccer field and swimming pool — and it’s surrounded by vineyards and olive groves, so if you plan your visit during the harvest, you can even take part in the vendemmia or the raccolta di olive. The villa sleeps 16 guests and has a bright, luminous kitchen and an outdoor gazebo for dining al fresco.
Local experience: While you’re near Florence, don’t miss exploring secret artisan workshops in the Oltrarno neighborhood. N2S can arrange special behind-the-scenes visits to a historic leatherworker, a goldsmith that creates jewelry to vendors on the Ponte Vecchio, and a mosaicist who creates art in the local Florentine tradition.
An Architectural Marvel In Chianti
The details: Set halfway between Florence and Siena, this stylish farmhouse-turned-luxury villa is one of Chianti’s finest. Owned and designed by one of Tuscany’s leading antique dealer families, this home has been decorated with unique pieces collected around the world and — and its interiors have been featured in the pages of Architectural Digest, among others. The grounds offer panoramic views of the countryside and feature an infinity pool, botanical garden, outdoor patios and a small family chapel. This villa is a short drive from some of Tuscany’s most beautiful towns, including San Gimignano and Volterra.
Local experience: Chianti is the perfect place to enjoy Tuscany’s longstanding enological traditions. Hop into a vintage Land Rover 4×4 and taste the latest vintages at our favorite local wineries before it’s time for lunch. You’ll dine on freshly made pasta and seasonal dishes on a private, panoramic terrace overlooking the countryside.
An Aristocratic Residence Near Siena
The details: Owned by a noble Roman family, this 15th-century residence is a museum unto itself and gives guests a rare glimpse into Italy’s aristocratic history. It’s strategic location near Colle Val d’Elsa means you can explore the artistic legacy of Siena and the celebrated wineries of Montalcino, where we can arrange a private candlelit dinner by a Michelin-starred chef in a deconsecrated chapel. The villa features antique furnishings passed down through generations, luxurious living areas, multiple game rooms, a tennis court and a large swimming pool. The property sleeps 25 guests, making it a perfect rental for an intimate wedding or family reunion.
Local experience: Learn about the historic Palio di Siena firsthand from a jokey who participates in the famous horserace each year. You’ll be welcomed into his home to dine with his family, admire his trophies, tour his stable and learn the legends surrounding one of Italy’s most unique events.
A Charming Villa Outside Lucca And Pisa
The details: If you’ve already been to Tuscany and are looking to experience a different side of this popular region, we recommend exploring the northern area around Lucca. And this five-bedroom farmhouse is a set on a hill, off a paved country road and through a private gate, is the is the perfect place to do just that. It’s a beautiful, verdant oasis surrounded by rolling hills and perfect for nature lovers who want to unwind during their stay. Bike through the woods, lounge by the pool and bake a margherita in your own outdoor pizza oven. On a clear day, you can just make out the Leaning Tower of Pisa in the distance.
Local experience: This is a great base to explore the northern Tuscan coastline, including the beach at Marina di Pietrasanta and the marble quarries of Carrara, where Michelangelo selected the marble for his legendary works. You can even venture into Liguria and sail around the Cinque Terre and Portovenere abroad your own private boat.
A Luxurious Escape Along Tuscany’s Southern Coast
The details: This expansive estate is one of the leading luxury villas in Tuscany. Set within the ruins of an ancient monastery, it has been meticulously converted into a resort that sleeps 18 guests. The beauty of this villa is you’re located between cielo, mare e terra — sky, sea and earth. With wide, open spaces and natural elements, it’s a great place to host a wellness retreat or a bohemian wedding. The saltwater, infinity swimming pool is a highlight and offers sweeping views of the nearby islands of Giglio and Montecristo. This villa also has a yoga area, jacuzzi, steam room and massage area.
Local experience: With its turquoise and hidden grottos, Monte Argentario is one of Tuscany’s best-kept secrets. We highly recommend a day exploring the archipelago by sea. Horseback riders will also love exploring the wild Maremma countryside with local Butteri, Tuscan cowboys, who still wrangle their herds according to ancient tradition.
A Boutique Farmhouse In The Val d’Orcia
The details: Surrounded by the rolling hills of the Val d’Orcia, this stylish farmhouse sleeps 19 guests and has a bountiful vegetable garden, large terrace with pergola, a heated swimming pool and panoramic jacuzzi. The annex, a historic barn next to the main villa, has a spacious playroom which is perfect for yoga or group exercises, so this is a nice villa for retreats as well. Nearby you can soak Tuscany’s thermal springs in Bagni San Filippo and Bagno Vignoni or explore the manicured gardens at Villa La Foce. It is a short drive to famous towns including Montepulciano, Montalcino and Pienza.
Unique experiences: This villa and its location give you a chance to reconnect with the land and the Val d’Orcia’s best local products. Enjoy the region’s famous pecorino di Pienza at a renowned caseificio and taste some of best wine in Tuscany during a tailormade tour of our favorite local estates.