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Italian Vacations Villas in Tuscany

With its vine-draped rolling hills, spire-straight cypress trees, creamy clay colored villas, and flower-bedecked ancient towns, Tuscany invites visitors to take a slow and whimsical passeggiata (leisurely stroll) through its rolling hills.

However, the magnificent aesthetics are only an adornment of the evocative, rich culture. Tuscany invites you to walk in the footsteps of history while celebrating the most prized of modern indulgences for a Tuscany vacation that epitomizes la dolce vita.

We have assembled a hand-picked collection of Tuscany villa rentals to make your next Tuscany vacation one that will inspire struggimento for years to come. Do you have a question about our Tuscany vacation villas, or would you like to dive right in and start your search for the best Tuscan villa rental?

Featured Tuscany Villa Rentals

WIMCO Villas,  Italy Vacation rentals BRV GEG, Italy, Tuscany/Siena Vacation home rentals, Tuscany/Siena Villas

Alfieri (BRV GEG)

Strikingly beautiful restored country house, stunning panorama of Tuscan hills, beautiful pool

5 br / 5 ba
$1990 - $2041/Night

WIMCO Villas,  Italy Vacation rentals SAL FON, Italy, Tuscany/Val D Orcia Vacation home rentals, Tuscany/Val D Orcia Villas

Fontanelle (SAL FON)

Lovely property, spectacular position with views of surrounding hills, featured in several magazines

5 br / 5 ba
$834 - $1374/Night

WIMCO Villas,  Italy Vacation rentals BRV ERA, Italy, Tuscany Vacation home rentals, Tuscany Villas

Erato (BRV ERA)

Carefully restored farmhouse with exquisite views of countryside, heated pool, helipad on site

3 br / 3.5 ba
Price on Request

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Luxury Tuscany Vacation Villa Rental

View of Volterra, Italy of the Pisa Province

Indulge in the Soul & Vibrancy of Tuscany with a Luxurious Tuscany Villa Rental

"Rome and New York were impressive, but they knew they were... There was a raw, feral beauty about [the Tuscan] landscape... this was innocent, natural beauty, the best kind, like a woman first thing in the morning, lit up by the sun streaming through a window, who doesn't quite believe it when you tell her how beautiful she is." – Leonardo Donofrio, Old Country

Tuscany is the picturesque central region of Italy stretching between the Apennine mountains to the azure-blue Tyrrhenian Sea. Its lyrical landscapes, rich heritage, and art-rich cities make Tuscany a prized vacation destination for visitors around the world.

Whether you're an art-lover or beholder of ancient culture, a connoisseur of fine wines or someone who loves to bask in the ethereal glow of sun-soaked landscape, Tuscany offers a vacation of a lifetime.

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Private Tuscany Villas

Villa Cipresso in Chianti, Tuscany

Why Choose to Rent Tuscany Villas?

Life in Tuscany is relaxed and unhurried making it uniquely suited for villa life. Enjoy a morning cappuccino and biscotti al fresco on a sundeck with panoramic views. Walk to the Pontile di Forte del Marmi for a morning stroll along the water. Or take a refreshing dip in your private pool before exploring the historical towns and indulging in the region's famous wines.

Renting a villa in Tuscany not only means you get a comfortable and scenic home to yourselves, it also means you're taking in the Tuscan sites more authentically. While Tuscany is home to some of the most extravagant designers, including Guccio Gucci and Salvatore Ferragamo, Tuscany is not about lavish extravagance. It's about understated, natural beauty.

In addition, renting a Tuscany villa can be cost-efficient—and more fun than staying in a hotel—when you're traveling with a group. A private villa rental means you don't have to book multiple hotel rooms. It also often means private patios, sundecks, swimming pools, kitchens, dining areas, and more. If your group would like additional services to make your stay more comfortable, such as grocery delivery, car service, private chefs, or other needs, The concierge team at WIMCO Villas is happy to arrange it all at no extra cost

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The Most Popular Vacation Villas in Tuscany, Italy

Below you'll find some of our most popular vacation villas in Tuscany, including highly sought after agriturismos (or stone farmhouses), picturesque apartments in the heart of the city, and large, luxurious estates.

Popular Vacation Villas in Tuscany, Italy

Villa Mara in Florence, Tuscany

Florence Villas

"Surprisingly small as it is, Florence looms large on the world's 'must-sees' list—and not just for its unmatched treasure chest of art. Rich in culture, backdropped by history and anchored by family, faith and food, the Florentine lifestyle is enviably sweet." –

Picturesque and rich with culture, Florence is one of the top choices for travelers seeking to visit Tuscany. The birthplace of the Renaissance, Florence is draped in art, history, and architecture. In addition to its appreciation of heritage, Florence is also ripe with modern luxuries including high-end designer shops (with brands like Prada, Gucci, and Salvatore Ferragamo), authentic Tuscan cuisine, and—of course—an abundance of local wine.

Although Florence is a city, it feels slower and calmer than its famous tourist counterparts. While streets may be filled with pedestrians, visitors stroll with an unhurried gait—often enjoying a gelato while they window shop. Take time to marvel at the architecture and take in the local art. You may also enjoy exploring landmarks such as the Santa Maria del Flore cathedral and the famous Uffizi art gallery which houses masterpieces from historical artists including Michelangelo and Botticelli.

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Tuscany Villas for Rent in Siena, Italy

Villa Alfieri in Siena

Siena Villas

Siena is a small and romantic medieval city sitting atop 3 rolling hills in the center of Tuscany. At the heart of Siena is the Piazza Del Campo which hosts the world famous Palio, a festival hallmarked by its horse race that overtakes the square twice a year and draws spectators from around the globe. Outside of Palio time, the square is perfect for a leisurely stroll or to indulge in the simple yet flavorful Tuscan cuisine.

Siena is a chef's dream, with the largest market in Tuscany held every Wednesday at La Lizza from 8:30 to 1:30. Visit early to handpick some of the finest local meats, cheeses, oils, and wines in the region to try your own cucina povera cooking in your villa's gorgeous kitchen. Did we mention cooking classes and demonstrations—or a private chef, if you prefer—are available for guests?

While in Siena, explore the Public Palace with its spectacular Torre del Mangia. If you brave the 400-step climb to the top, you'll be rewarded with a glorious panoramic view of the town and surrounding countryside. The Duomo di Siena is an Italian Gothic masterpiece, and one of the most beautiful churches of Italy. If you seek a retreat from the city, you can find an easy and airy escape to the countryside for rows of vineyards, cypress trees, olive groves, ancient hamlets, or natural hot springs and spas.

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Tuscany Villas for Rent in Lucca, Italy

Villa Controni in Lucca, Italy

Lucca Villas

A historic city surrounded by immense city walls, Lucca has some of the most incredible architecture, natural beauty, music, and food in Tuscany.

Its wide city walls are so broad that they are topped with a road, making it a popular way for runners and cyclists to explore the perimeter of the city. For those fresh air lovers who prefer hiking, Lucca is a paradise with the Cinque Terre only an hour away and the gorgeous Garfagnana mountains to the north.

More than its outdoors scene, however, Lucca is known for its music and cuisine. Lucca hosts a Summer Music Festival which welcomes famous artists from around the globe to perform in the open-air Piazza Napoleone throughout July. Lucca is also known for having some of the best food in Tuscany with richer, more decadent dishes compared to traditional Tuscan fare.

Lucca's city grounds include historical medieval and renaissance architecture such as the Church of San Michele in Foro, the Torre delle Ore, the Guinigi Tower, and the Acquedotto del Nottolini. Lucca also has some of the most beautifully-preserved villas and gardens in Tuscany.

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Tuscany Villas in Chianti, Vacation Rentals Italy

Villa La Maccinaia in Chianti, Tuscany

Chianti Villas

Bedecked in sun-speckled, vine-draped hills, dense forests, and historic olive groves, Chianti is home to some of the most beautiful villas for rent in Tuscany. Chianti is best known for its picture-perfect scenery, postcard-worthy agriturismos, and the region's famous Chianti Classico wine.

Most travelers who visit Chianti come for the romantic wine country atmosphere. In addition to the beautiful rolling hills and vineyards, visitors can bask in the flower-bedecked stone villages such as Montefioralle. These villages are beautiful and charming, with cobblestone paths, rustic archways, and doorsteps adorned with pots of colorful flowers.

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Vacation Tuscany Villas for Rent in Maremma, Italy

Villa Marchesa in Maremma, Tuscany

Maremma Villas

Fall in love with the Maremma Coast in Southern Tuscany. With its relaxed pace, vast countryside, and breathtaking beaches, Maremma seems to be plucked straight from a daydream.

Serene and sleepy, Maremma stretches between the provinces of Livorno and Grosetto and has a breathtaking array of landscapes from long beaches to black rock and hills covered in dense woods.

In Maremma, you'll find remote, quintessential pocket beaches and coves framed by stately umbrella pines and low-slung hills. Enjoy rambling estates, monastic ruins, silvery olive groves, and lagoons, with plenty of fresh seafood and sunbathing to spare. Maremma wraps food, wine, and scenery into a uniquely chic and discreet getaway.

Your Maremma villa rental will offer a mellow and dreamy escape from your hometown bustle, bringing peace and relaxation to your Tuscany vacation. Whether you're visiting Maremma for its quiet villas or sleepy hamlets, WIMCO can help create the vacation of your dreams.

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Luxury Tuscany Villas for Rent

Villa Il Lupinaio in Maremma, Tuscany

Luxury Tuscany Villas for Rent

The WIMCO Villas vacation team is a seasoned expert in providing the best private villa rentals and villa vacations in Tuscany and the surrounding area. Not only will our vacation concierge help you find and book the perfect villa for your group, we will also set up flights, car rentals, grocery delivery, reserve private wine tastings and gallery tours, and any additional services or requests you may have for your vacation.

Explore our Tuscany villa rentals below or speak with a travel concierge so we can start designing your dream vacation.

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Tuscany Vacation Ideas

Plan Your Tuscany Vacation

Tuscan Hotels

Tuscany and its capital, Florence are home to several of the worlds most fabulous luxury hotels. WIMCO is proud to feature distinctive luxury hotels in Florence.

Featured Tuscany Hotels and Resorts

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