Chianti is easy to fall in love with. From the region’s expansive views, rolling hills covered in vineyards, and charming scenes of everyday life in quaint local Chianti villages, it will be easy to convince family and friends to join you on a trip to Chianti, Tuscany!

The first step is to choose where to stay. Chianti has many options in many towns, including farm stays, bed-and-breakfasts, hotels, apartments, and luxury villas that will blow you away.

We have compiled a list of the top handpicked villas in Chianti, with wonderful features such as a swimming pool or great location, so you can quickly find the perfect Chianti villa for you and your group of friends or family. Some are for big family reunions, weddings, or several couples. In contrast, others are perfect for a family of 6, and there is even one perfect for a couple or single person traveling alone.

This renowned wine region is home to some of the most amazing luxury Chianti villas. Anywhere you choose, you will find that the location is perfect for exploring the rest of Tuscany, such as San Gimignano, Monteriggioni, Arezzo, Lucca, Pisa, Florence, and Siena.

Villa Benedetta in Greve in Chianti for a large group or wedding

Villa Benedetta in Greve in Chianti
Villa Benedetta

Villa Benedetta is located just minutes away from the beautiful small town of Greve in Chianti in the very heart of the Chianti region in Tuscany. It is the perfect location for a family reunion or large group trip to Italy. It can even accommodate weddings or other celebrations in Tuscany, so be sure to inquire directly with them if you are hoping to get married in Tuscany.

The vacation rental is a historical residence immersed in the Tuscan countryside and is owned by the Folonari family, who has been involved in Chianti Classico wine-making for many years and is still making wine from vineyards near the house. Villa Benedetta was renovated in 2014 and is surrounded by fantastic private gardens with stunning views. There is a barbecue, a covered gazebo for up to 20 people, a private swimming pool with a changing area, and a full bathroom witha shower in the pool area.

This magnificent villa in Chianti comfortably sleeps up to 20 people in its 9 rooms and 8 bathrooms. It has a stunning, well-equipped kitchen, dining area, and plenty of indoor and outdoor spaces to enjoy alfresco dining or even have a romantic and unforgettable wedding in Tuscany.

The location is within easy walking distance of Greve in Chianti, allowing you to enjoy everyday life in a Chianti village and spend time in the main square, Piazza Matteotti, reachable on foot in about 10 minutes or by car in just 3 minutes.

The area has endless choices for Chianti Classico wine tasting (including on the property!), fine dining restaurants, grocery stores, artisan shops, and Tuscan butchers. There is also a nearby bus stop. The iconic cities of Florence, San Gimignano, and Siena are all just 30 minutes away by car.

Villa Sonia in Chianti for a multi-generational stay with a private pool

Villa Sonia in Chianti
Villa Sonia /

Villa Sonia is a large private villa in the Chianti region of Tuscany. It has a private pool and a lovely garden with fantastic views of the Chianti Classico landscape, vineyards, olive groves, and woodland areas. The holiday rental lies almost exactly halfway between Florence and Siena. It is just a few minutes away from the charming medieval town of San Donato in Poggio, with restaurants, shops, and much more.

The holiday rental has six air-conditioned bedrooms and six bathrooms and can sleep up to 12 people. Its amenities include air conditioning and a Wi-Fi internet connection. Near the swimming pool is a furnished outdoor sitting and dining area, ping-pong table, and exercise room with a treadmill and bike. Free parking is available directly on the property.

The villa is perfect for a multi-generational trip. It has a main house and three separate air-conditioned units so that family members can have their privacy and enjoy time together in the Chianti hills or splashing around in the private pool. Additional space to sleep more people may be possible, but it is not included in the rental price.

Villa Andrei in San Casciano Val di Pesa countryside living

Villa Andrei
Villa Andrei /

Just 20 minutes outside of Florence, Villa Andrei is super convenient for exploring the Chianti region and visiting beautiful Tuscan cities like Florence and Siena while at the same time having a quiet vacation rental villa in Chianti where your family or group of friends can relax and enjoy the dolce vita.

The typical Tuscan farmhouse villa has 4 bedrooms and 2 bathrooms. It also has a large living room, dining room, well-equipped kitchen, and billiards room for plenty of fun and relaxation.

A gigantic garden and extensive olive grove surround the villa. The outside area features a barbecue facility and spacious covered patios for al fresco dining. The garden offers views of unforgettable sunsets over the Chianti hills. There is also an above-ground pool and hot tub. Onsite parking is available at no extra cost.

Because of its unique location in the countryside of Tuscany, mountain bike enthusiasts will be thrilled with the many trails and possibilities for exploring the Chianti region by bike. It is in the heart of the Chianti Classico region, with hundreds of wineries within minutes of the property. Not far away are some of Tuscany’s world-famous destinations, such as Greve in Chianti, Monteriggioni, San Gimignano, Radda in Chianti, and many others, including Florence and Siena.

Villa Casa al Monte in Greve in Chianti exclusive retreat

This luxury Chianti villa is located in the heart of the Chianti Classico region in the rolling hills near Greve in Chianti. It is an exclusive, gated property, and parking is available directly on-site. We highly recommend having a car to access this property because of its location.

This Tuscan countryside villa’s seven fully air-conditioned bedrooms and six bathrooms can accommodate a total of 14 people. Guests can relax and enjoy the property, which includes two living rooms, two well-equipped kitchens, a gym, satellite TV, fully air-conditioned bedrooms, and lots of space to relax and have fun.

The outside area surrounding the villa has a fenced and terraced garden, a furnished gazebo, a ping pong table, a loggia with a table perfect for outdoor meals, a barbecue as well as a private pool, and a hot tub that is open from June to September.

Because of the large garden, it is one of the most peaceful villas in Tuscany and offers ample privacy while fully air-conditioned. The surrounding countryside has woods, vineyards, and olive groves to explore. The location near Greve in Chianti makes it perfect for exploring the rest of the Chianti Classico region, and it is one of our top holiday villas in Chianti.

Villa Aurora in Certaldo with a private pool and patio

Villa Aurora
Villa Aurora /

Villa Aurora is a modern-style villa for rent near the charming town of Certaldo, Tuscany, within the beautiful Chianti countryside. It has four bedrooms, sleeping eight people, all open onto patios, and four bathrooms. The luxury amenities include air-conditioned bedrooms, a private pool, a fireplace, a washing machine, and a fully equipped kitchen with microwave, tea, and coffee machines.

This villa has one of our favorite private pools in Italy. Its unique shape makes it look like a pond. A charming grassy area and a garden with lounge chairs and umbrellas surround it. There is also a fitness room and hot tub.

Certaldo is a fantastic location very close to San Gimignano, Volterra, Colle di Val d’Elsa, Poggibonsi, Siena, and all the Chianti Classico region.

Villa Il Pollaio Tavarnelle Val di Pesa for 1 or 2 people

This restored farmhouse has been recently renovated and turned into six smaller apartment villas in Chianti, including Il Pollaio, the smallest. It is in a super convenient location halfway between Florence and Siena, nestled in the gentle hills of the Chianti Classico region. Just off the ancient Roman Cassia road, it is within walking distance of the charming Tavarnelle Barberino area.

You will find Villa Il Pollaio within the main villa, with a garden filled with lavender and roses. The fully air-conditioned apartment has a lovely view of the private pool shared with the other apartments. It offers umbrellas, chairs, sun loungers, and sun beds for all guests. It has one bedroom and one bathroom with a shower, a fully equipped kitchen, a living room, and a private covered patio with a table and chairs.

The apartment has air conditioning, bed linen provided, window screens, Wi-Fi, satellite TV, and free parking is provided on the property. You get all the amenities of the larger villas in Chianti, like a private pool, without the big price tag, making it perfect for a couple or single traveler with a car.

This apartment is in Barberino Tavarnelle, with stunning views of the Chianti area. Many wineries and great restaurants are just a short distance away. Besides wine tasting, you can visit the Alta Val d’Elsa River park, swim in the summer, or see the stars at the Chianti Observatory nearby.

Villa La Valle, a luxurious Tuscan estate near Florence

Villa La Valle
Villa La Valle /

If you want to be near Florence but still in the Chianti Classico region, Villa La Valle is the perfect luxury Chianti villa with a private pool for you. Just 12 miles from the center of Florence, it offers a relaxing and beautiful retreat in the beautiful Chianti hills.

The owners did an incredible restoration of the property not long ago, creating a 5-bedroom, 4-1/2-bath holiday house that is one of our favorite Chianti villas under the Tuscan sun. There are luxury touches like marble in the bathrooms, hand-made French cabinets, and a fully equipped gourmet kitchen.

The family room has a gigantic stone fireplace that can be used for barbecue and an entertainment system with lots of movies and music to choose from at no additional cost. All bedrooms are air-conditioned.

This luxury villa near Florence had a main house and a guest house with its own kitchen and coffee machine, and it is an ideal property for up to four couples or two families with children. The outside area is just as fantastic, with a saltwater swimming pool, sunbathing area, and views of nearby castles. There is an organic garden for fresh produce, a wood-fired pizza oven, and plenty of space for al fresco dining under a pergola covered in grapevines.

You can hike on the 2000-year-old Roman road, find a swimming hole in a river, and spend countless hours hiking in the endless trails just a short distance away. There are numerous Chianti villages within a 10-minute drive, with restaurants, food markets, pharmacies, cafes, and wineries galore. You can also visit the iconic cities of San Gimignano, Pisa, Lucca, Montalcino, Montepulciano, and nearby Florence, with Piazza della Signoria only 20 km away.

Villa Casale Santappiano in Barberino Val d’Elsa an entire hamlet

Villa Casale Santappiano is a small renovated village down an unpaved road with five charming apartments that are rented all together and are perfect for groups looking for plenty of privacy as well as large common spaces. Each apartment boasts a private entrance, veranda, and outdoor eating area.

The hamlet is located within the Chianti region, with easy access to nearby large cities such as Florence and Siena. The outdoor shared area has a large garden, a panoramic view, a swimming pool, and a hot tub.

Lots of additional services are available at the villa, including professional chef service to prepare meals during indoor or outdoor dining, as well as babysitting services, and cooking lessons.

Villa Chianti in Marcialla village with vineyard view

Villa Chianti
Villa Chianti /

If you love staying in a small village with a panoramic view of Chianti vineyards, Villa Chianti is your choice. Nestled in the Chianti village of Marcialla, this villa in Chianti is spread over two floors. It includes a kitchen with a coffee maker, a Nespresso machine, plenty of cooking utensils, a dining and living room, four bedrooms, and 3 1/2 bathrooms.

The outside area includes a heated hot tub with whirlpool jets and incredible views to the surrounding countryside. There is ample outdoor dining, and you can sip a glass of Chianti wine while viewing the vines from which it was produced. Parking is free of charge in front of the house.

In the vicinity, you can explore the Chianti towns, go olive oil or wine tasting in the Tuscan countryside, take a cooking class, or visit the museums and churches of Florence, San Gimignano, or Siena.


What kind of activities can be done from villas in Chianti?

Given the number of tourists who come to this region every year, there are so many fun extra services you can arrange to enjoy, such as cooking lessons, visits to local wine cellars and wine tasting, olive oil tasting, honey tasting, pizza making, private chef services, private guided tours of Florence with skip-the-lines tickets to see Michelangelo’s David or the Uffizi Gallery, and this is only the beginning of the activities offered in Tuscany.

Where is the Chianti region?

The Chianti Classico is a wine region between Florence and Siena. Many of the towns changed their names and added “in Chianti” so they could be easily identified as lying within the famous wine-making region, for example, Radda in Chianti, Greve in Chianti, Castellina in Chianti, and many more.

But Chianti Classico isn’t the only Chianti wine region; in fact, the general Chianti area is much, much larger. There are a total of eight Chianti regions: Chianti Classico, Chianti Colli Aretini, Chianti Colli Fiorentini, Chianti Colline Pisane, Chianti Colli Senesi, Chianti Montalbano, Chianti Montespertoli, and Chianti Rufina.

Do any villas in Chianti, Tuscany, have private pools or a tennis court?

While many Italian villas in Chianti have private pools, sometimes even a heated pool, it is rare to find a tennis court, but not impossible. We recommend selecting it in your search criteria through villas in Italy.