Discover a selection of 8,000 vacation rentals in Chianti Region, IT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $105 per night, and villas and farmhouses are popular options for a stay in Chianti Region. Either way, you'll find a rental for everyone's needs.
Destination guide

Why people love visiting rustic Chianti Region

Enjoy the wineries and other features of Chianti Region. This city is relaxing and scenic, recognized for its local tours, sightseeing and restaurants. Take in top local attractions like Stadio Artemio Franchi and Piazza del Campo. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Activities and attractions in Chianti Region

Do you want to discover attractions to visit during your stay? Venture out of your cozy vacation rental and experience everything that makes Chianti Region a one-of-a-kind vacation spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Il Molino di Grace Winery (2.3 mi / 3.7 km)
  • Castello di Radda Winery (2.6 mi / 4.1 km)
  • Castello d'Albola (2.8 mi / 4.5 km)
  • Buondonno Winery (3.9 mi / 6.2 km)
  • Casa Vinicola Luigi Cecchi (5.3 mi / 8.5 km)
  • Isole e Olena Winery (6 mi / 9.7 km)
Natural features

Exploring the natural features in Chianti Region

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chianti Region is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Piazzale Michelangelo (16.5 mi / 26.6 km)
  • Boboli Gardens (16.7 mi / 26.9 km)
  • Gianfranco Carla Fineschi Botanical Rose Garden (7.6 mi / 12.2 km)
  • Chianti Sculpture Park (9.6 mi / 15.5 km)
  • The SottoVico Garden (12.7 mi / 20.4 km)
  • Enoteca Italiana (14.5 mi / 23.3 km)
How to get there

Traveling to and around Chianti Region

The nearest airport is in Florence (FLR-Peretola), located 20.1 mi (32.4 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Pisa (PSA-Galileo Galilei), which is 49 mi (78.8 km) away.

If you prefer to travel by train, Figline Valdarno Station, San Giovanni Valdarno Station and Incisa Station are the main stations that serve the city.

How many vacation rentals are available around Chianti Region, IT?

Our 2020 property listings offer a large selection of 8,392 vacation rentals around Chianti Region. From 1,491 villa rentals to 366 farmhouse rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Chianti Region?

There are many lovely places to stay for a holiday trip or just for a weekend in Chianti Region. From Vrbo travelers, the top most popular destinations to visit are:

  • Florence: 4,536 vacation rentals
  • Santo Spirito: 975 vacation rentals
  • San Giovanni: 1,214 vacation rentals
  • Sant' Ambrogio: 1,965 vacation rentals
  • Duomo: 1,841 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Chianti Region! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Chianti Region?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chianti Region:

  • Florence: 4,536 rentals
  • Greve in Chianti: 4,046 rentals
  • San Gimignano: 3,840 rentals
  • Siena: 2,296 rentals
  • Gaiole in Chianti: 1,540 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Chianti Region?

Vrbo offers a large selection of rentals near lovely places in Chianti Region. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Basilica of Santa Croce: 1,538 rentals
  • Ponte Vecchio: 1,603 rentals
  • Castello di Monsanto: 7,250 rentals
  • Piazza Matteotti: 8,836 rentals
  • Piazza del Duomo: 6,934 rentals

But there are many other points of interest around Chianti Region listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Chianti Region

4,536 vacation rentals
Greve in Chianti
4,046 vacation rentals
San Gimignano
3,840 vacation rentals
2,296 vacation rentals
Gaiole in Chianti
1,540 vacation rentals
Castellina in Chianti
2,685 vacation rentals
3,899 vacation rentals
San Casciano in Val di Pesa
882 vacation rentals
Castelnuovo Berardenga
3,274 vacation rentals
Gambassi Terme
3,256 vacation rentals
1,704 vacation rentals
5,724 vacation rentals
3,150 vacation rentals
2,504 vacation rentals
2,227 vacation rentals
1,968 vacation rentals
Colle di Val d'Elsa
3,499 vacation rentals
1,761 vacation rentals
Casole d'Elsa
1,389 vacation rentals
1,744 vacation rentals