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Chianti Villas & Luxury Vacation Rentals

Luxury Villa Rentals for 2+ people

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Your Guide to Chianti Villas

Located in the heart of Tuscany between Florence and Siena, Chianti is one of the most celebrated wine-making regions in the world. Chianti villas let you experience the quieter side of this historic area, so you can take in all that it has to offer.

Chianti has been a wine-making region ever since the Etruscans and later the Romans discovered its potential for viniculture. It was developed substantially during the Renaissance, with the Medici family investing in grand estates and promoting Chianti wine.

Today, the Chianti Classico label testifies to the region’s strict standards for winemaking, while Chianti villas have emerged as some of the best in Tuscany.

Renting a luxury villa in Chianti is easy with Rental Escapes. First, choose your travel dates. Next, choose your party size. From there, your Rental Escapes Villa Specialist will happily present you with the best available Chianti villas for your group. After, your Concierge customizes your trip, including transportation, chef service, excursions, and more.

Chianti Villa Rentals

Like the region itself, Chianti villas are rife with history. Think restored farmhouses with stone walls, terracotta roofs, and large terraces. That said, they also often feature plenty of modern amenities, including heated pools, private gyms, gourmet kitchens, and more.

Chianti villas can be found all around the region, including in Greve, considered the gateway to Chianti; Radicondoli, a serene hilltop village; Panzano, which prides itself on its wine and culinary reputation; Castellina, with its Etruscan roots and archaeological sites; Radda, with its narrow streets and medieval walls; and more.

Regardless of where you stay, you can expect to be charmed by the panoramic views and fresh, effervescent air of this fabled countryside. You can also expect 5-star service, including from your Rental Escapes Concierge.

Luxury Villas Chianti

Chianti is closely associated with fine wine, great food, and stunning landscapes. Luxury villas in Chianti let you experience all of the above in stays that are at once historic and modern. They include:

Vinia: A recently restored farmhouse, Vinia offers an elevated rustic experience in the heart of Chianti. With a modern interior and features like a unique pool, a large outdoor dining area, and a covered fireplace, Vinia has everything you need for the ultimate Tuscan holiday.

Villa Melissa: Spanning over 20 acres, Villa Melissa is perfectly located near Greve, giving access to many of Chianti’s best villages. It also features 2 indoor and 2 outdoor swimming pools, a 4-person jacuzzi, stunning Mediterranean gardens, and more. A perfect base for up to 37 guests.

Vitigliano: A traditional Tuscan villa with a rustic brick façade and terracotta tiles, Vitigliano blends Italian style with modern convenience. It features six spacious en-suite bedrooms, a wellness center, a sprawling private garden, and even an onsite chapel. This is a great space for events like weddings, baptisms, and other ceremonies.

Chianti Villas with Pools

Tuscany’s weather in the warmer months imparts the region with a sense of rejuvenation. Chianti villas with pools let you experience this feeling in a fun, private way. They include:

Triofante: A traditional Tuscan villa surrounded by a verdant Mediterranean garden, Triofante is the perfect place to relax and take in the Tuscan sun. It’s also just a short drive to the village of Sambuca, where you can enjoy narrow streets, stone buildings, and an authentic Tuscan atmosphere.

Verdiana: Nestled along vineyards and olive trees, Verdiana offers a dreamy atmosphere. It combines rustic surfaces with plush furnishings for comfort, while the swimming pool, gym, and Turkish bath promise further renewal. A great choice for wine lovers.

Davinia: Set between Greve and Panzano, Davinia is composed of three separate buildings brought together by communal spaces. It’s all punctuated by panoramic views of the surrounding valleys and vineyards, including from the terraced swimming pool. A great choice for groups traveling together.

Chianti Villas for Families

So much of Tuscan life is about spending quality time with your loved ones and sharing good food and wine. Chianti villas for families let you do just that with comfy, accessible stays that offer something for everyone. They include:

Morea: Perfectly located between Florence and Tuscany, Morea is a true family villa with tons of fun features. There’s a children’s play area, a tree house, a billiard room, an entertainment room, a sprawling veranda, and so much more. Perfect for multigenerational groups.

Leonardo: A spacious country home, Leonardo has been restored inside and out to create a simple elegance. Take a dip in the pool. Enjoy a meal al fresco. Admire the stunning views. This is Tuscan living.

Chianti Villas FAQ

What are the Entry Requirements for Italy?

Italy is part of the Schengen zone, so you only need to show a valid passport once upon entry. You may need an additional tourist visa if you’re traveling from outside the US, Canada, EU, Australia, or New Zealand.

How to Travel to Chianti?

Most visitors will fly into Chianti. The closest airport is in Florence, which is about 50km away, as well as the Pisa airport about 100km away. Chianti can also be reached by train from Rome by taking a 1.5-hour train to Florence. From Florence, you can drive or take regional trains into different towns in Chianti. Your Rental Escapes Concierge can help with airport transfers and plane tickets.

How to Get Around Chianti?

The best way to get around Chianti is by renting a car. A car rental will let you see more of the countryside, as well as let you explore the many charming towns around Chianti. The SR222, also known as the Chiantigiana road, is also particularly scenic and connects historic towns like Greve, Radda, and Castellina. Taxis and private drivers are also available. Your Rental Escapes concierge can help with rental cars, private drivers, and any other transportation needs.

When is the Best Time to Visit Chianti?

High season in Chianti is from June to August. The weather is warm, there’s a vibrant atmosphere, and the harvest season starts in late August. This is an ideal time for wine tours, lounging by the pool, and enjoying the landscapes, though crowds are at their peak.
Shoulder season is from March to May and September to October. The weather is perfect for sightseeing, and autumn in particular sees stunning fall colors and the peak of harvest season. For many, this is the best time of year to go.
Off season is from November to February. The weather is coolest, but there’s a peaceful ambiance and a festive spirit during the holidays. This is a great time to experience Chianti like a local.

Is Chianti Safe?

Chianti is very safe. It’s known for its peaceful countryside and welcoming locals, and it has a very low crime rate. That said, do watch for pickpockets in busier tourist sites, and be mindful of sun exposure in the summer.

Best Things to do in Chianti?

Go on a wine tasting: Chianti is home to world-renowned wineries and vineyards. Many combine tours and wine-tasting, giving you a chance to experience the history and magic of the region firsthand.
Visit historic villages: Towns like Greve, Radda, and Castellina create a rich historic mosaic. Narrow streets, ancient town walls, fortresses – these towns exude a one-of-a-kind medieval charm.
Take in the countryside: Whether by hiking, cycling, or taking a hot air balloon, make sure you take advantage of the rolling hills and verdant scenery that has charmed so many visitors to Chianti throughout the ages.

How’s the Food in Chianti?

Along with its wine, Chianti is also known as one of the top food destinations in the world. It features a rustic yet refined cuisine that emphasizes fresh, local ingredients. Traditional dishes include Bistecca all Fiorentina, ribollita, panzanella, and more. Also, be sure to try the local olive oil, truffle, and pecorino cheese, as well as, of course, some chianti classico – the flagship wine of the region.
Your Rental Escapes Concierge can assist with restaurant reservations, private chef service, and villa pre-stocking.

How’s the Weather in Chianti?

Spring in Chianti is mild and pleasant, with average temperatures ranging from 10°C to 20°C (50°F to 68°F). Rainfall is moderate, averaging around 60-70 mm (2.4-2.8 inches) per month.
Summer in Chianti is warm to hot, with average temperatures ranging from 20°C to 30°C (68°F to 86°F). Rainfall is relatively low, with monthly averages around 30-40 mm (1.2-1.6 inches).
Autumn in Chianti is mild and comfortable, with average temperatures ranging from 15°C to 25°C (59°F to 77°F). Rainfall increases slightly, averaging around 70-80 mm (2.8-3.2 inches) per month.
Winter in Chianti is cool, with average temperatures ranging from 5°C to 10°C (41°F to 50°F). Rainfall is higher compared to other seasons, averaging around 80-90 mm (3.2-3.6 inches) per month, and occasional snowfall can occur.

Book a Chianti Villa with Rental Escapes

If you’re hoping to visit this beautiful part of Tuscany, Rental Escapes can elevate your Chianti villa rental into a true luxury experience.

Our portfolio includes the finest Chianti villas, including Chianti luxury villas, Chianti villas with pools, Chianti villas for families, and more.

Your Rental Escapes Reservations Expert can find the best luxury villa for your group, and your Concierge personalizes your trip to create the ultimate Chianti villa experience.

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