Nestled in the heart of Italy, Tuscany is a region that effortlessly embodies the essence of the country’s rich cultural heritage, stunning natural beauty, and timeless charm. This captivating area, often referred to as “Il Bel Paese” or “The Beautiful Country,” is celebrated for its rolling hills adorned with vineyards, ancient olive groves, picturesque villages, and a legacy steeped in art, history, and culinary excellence.

Tuscany’s magnetic allure has captured the imaginations of travelers, artists, and dreamers for centuries, making it a destination that beckons visitors to explore its treasures, savor its flavors, and immerse themselves in its captivating story.  

If you’re planning a trip to Tuscany, why not set the stage for the ideal vacation by staying in a quaint, rustic Tuscan cottage where guests have the opportunity to savor the local lifestyle? 

We’ve pulled together some amazing properties that will have you wanting to book your next trip to the Tuscany region

1779 Traditional Stone Cottage, Arezzo

Exterior of Historic Arezzo stone cottage.
Exterior of Historic Arezzo stone cottage. Photo courtesy of VRBO

This stone cottage is actually a converted chapel dating back to 1799 and lovingly restored with traditional Tuscan materials. The cottage features a queen bedroom, an en suite bathroom and a reading room with a fully fitted kitchen, dining and sitting room on the downstairs level and an extra twin bed in the living room. Double doors lead out to the garden and access to the secluded swimming pool. Barbeque facilities are available.

Guests will find an authentic stone pizza oven and a gazebo.

The cottage is 25 kilometers from the City of Arezzo. Other towns within easy driving distance include Cortona, Montepulciana, Siena and San Gimignano.

Casciano di Murlo, Siena

Located in the heart of the Tuscan countryside, this one-bedroom cottage also provides access to a garden and pool.

Casciano offers picturesque views of the surrounding hills, a shaded veranda with garden furniture and private barbecue. Guests will find a spacious living room with TV and double sofa bed, a kitchen and dining room (with washing machine, toaster and dishwasher), a triple room with a double bed and a single sofa bed, and a bath with shower.

Shops and restaurants are located nearby as are opportunities for hiking and walks in the beautiful natural surroundings.

Podere La Villa, San Casciano

It’s hard to beat staying in a gorgeous cottage villa offering stunning views of the Chianti hills. Not only will guests find peace and tranquility in this 3-bedroom, 3-bath villa, but the location is ideal. It’s just a few minutes from the town of San Casciano and only 15 kilometers to Florence.

Situated on two levels, the home boasts a pool, garden, a pergola-shaded terrace furnished with tables, chairs and a BBQ, wine from Podera’s own vineyards, a fully-equipped kitchen, and washer and dryer.

There are a number of easy, beautiful hikes to take directly from the property taking visitors through vineyards and wooded areas. The sunsets here are absolutely spectacular.

Historic Tuscan Cottage, Bucine, Toscana

Located in the triangle between Florence, Siena and Arezzo, this enchanting one-bedroom, one-bath Tuscan cottage offers convenient access to the three amazing cities and the stunning Chianti countryside.

One fascinating aspect of this property is The Limonaia, part of the complex of buildings making up the historic mill of Pogi (Il Mulino di Pogi), dating back to the 1400s. The Limonaia traces its origins to the middle of the 1600s, offering marvelous views of the grounds and the Ambra River from its eight arched windows located on each side of the building.

Home to numerous species of rare aquatic birds and ancient oak trees, the Mulino di Pogi property is a paradise for bird watchers, sport fishermen, and nature enthusiasts.

The Casetta Honeymoon Cottage, Seggiano

The Casseta Honeymoon cottage.
The Casseta Honeymoon cottage. Photo courtesy by VRBO

You don’t even have to be on your honeymoon to stay at this delightful one-bedroom, one-bath cottage that shares the property with a main farmhouse on a 10-acre Tuscan olive farm.

Though guests will find plenty of privacy, the cottage is also conveniently located to the medieval hilltop village of Seggiano that boasts a wonderful Italian restaurant.

The cottage’s living space includes a kitchen area, wood burning stove, dining and sitting areas with doors opening onto the olive grove beyond the covered porch. A spiral staircase leads up to the first-floor bedroom (one double and one single bed) plus an en suite shower room.

Cozy Stone Cottage, Brunello

Cozy cottage in Brunello.
Cozy cottage in Brunello. Photo courtesy of VRBO

This all-stone cottage house (a renovated barn) is situated on the rolling hills near the historic, medieval town of San Gimignano.

The two-bedroom, one-bath rustic cottage sits in an olive grove with picturesque views, and even has its own swimming pool. The property is centrally situated for visiting the most renowned historical and art centers in Tuscany, as well as many other smaller characteristic villages in the Chianti region, and within easy reach of the ‘Siena – Florence’ dual carriageway.

Restored Riverside Mill, Lucca

A beautifully-restored romantic property, this cottage in Lucca is off-the-beaten path offering peace and tranquility away from a busier Tuscany experience.

The two-bedroom, one-bath cottage sits in the midst of extensive gardens and also includes a bubbling trout stream, ideal for fishing or swimming.

The cottage also includes a log fireplace, terracotta tiled floors, and beamed ceilings.

The towns of Lucca, Pisa, Florence and Barga are not far away, and Castelnuovo, with its many restaurants, bars, outdoor swimming pool, station and famous market, is only a 10-minute drive.

Tuscan Countryside Cottage near Florence

Views from Tuscan Countryside Cottage near Florence.
Views from Tuscan Countryside Cottage near Florence. Photo courtesy of VRBO

For those looking to be a bit closer in to one of Tuscany’s most beautiful and well-known cities, this countryside cottage is a perfect choice.

The two-bedroom, two-bath vacation rental with an outdoor shower is hidden in the Tuscan countryside among olive groves, gardens, vineyards and woodlands offering plenty of privacy. However, downtown Florence is only a 20-minute drive away.

The property also borders the Chianti wine region, so guests have many opportunities for wine-tasting experiences, some within walking distance.

La Rota Cottage in Moncione

La Rota is a delightful cottage set among peaceful olive groves, barely a ten-minute stroll from the village of Moncioni, in the center of Tuscany’s “golden triangle” formed by Florence, Siena and Arezzo.  

Guests are within an hour’s drive of all three of these must-see Italian treasures, yet right in the midst of the fine red vintages of Chianti. The local village is only a 5 to 10-minute walk away along with a lovely bar shop and a new pizzeria/restaurant.

La Rota also boasts a private terrace equipped with sun loungers, huge shade umbrella and a table for candle-lit dining under the Tuscan stars.

Tuscany is one of my husband’s and my favorite regions in Italy, and a stay at one of these delightful cottages is the way to set the stage for an amazing Tuscany experience.

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