Chianti Accommodations

Rent a vacation home, villa or farmhouse accommodation in Chianti, Italy. Located near Greve in the Pisa region of Tuscany, the town of Chianti has its own rustic charm in the heart of Wine country. There is so much to experience, from art and gastronomic excursions to hiking and mountain biking through the olive groves and vineyards.

Your holiday lodging can be selected from vacation rentals in the beautiful wine region of Chianti, Italy’s most famous wine district. Villa rentals, apartment rentals and condo rentals can be found in the country side as well as in some of the surrounding cities. The region of Chianti covers approximately 64 square miles between Florence and Siena and borders such fabulous vacation destinations as Bologna, Pisa and Assisi.

To really get the feel of this lush olive and grape growing area, a vacation rental is the perfect accommodation. You will enjoy the freedom and quaint accommodations that await you.

Rent a car, a scooter, or even a bicycle to get around the hills and valleys and to follow the meandering roads leading you from modern cities to medieval castles high on the hill tops. In between, follow stream fed valleys through olive groves and vineyards. Some of the roads are unpaved and pot holed. You might want to join a wine tour and let someone else navigate and be responsible! Traverse through low mountains and ancient forests as you explore this world famous area in Italy. Rent your special Italian holiday lodging from owners of farmhouses, villas, cottages, home and apartments. Condo rentals, apartment rentals and villa rentals provide unique vacation experiences for relaxation. Take the time to feel like a local. Immersion in Italian culture can be achieved with vacation rentals such as villa rentals and apartment rentals.

Take a bus to a major city where you will find open markets, bookshops and souvenir stores. Ancient cities surround churches, statues and town squares. Festivals and celebrations are abundant, offering wine tasting and local foods, nuts and cured meats. Your vacation accommodations provide your Italian home away from home, in a condo rental, villa rental or apartment rental.
Chianti last minute deals on vacation homes will be highlighted in red if available. Start your accommodation search in Chianti now. Just enter your travel dates, number of travelers, and click 'search' for a list of properties for rent.

This resource can not be edited here.





View Map

12 Vacation Rentals

sort by

Sorry, there is no rental accommodation currently available in Chianti for your search criteria. Please change your search preferences or try a nearby region to increase the number of properties displayed.

  • Gorgeous Views of Volterra

    Volterra: Apartment in a villa
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #224210
    avg €212 EUR/night Credit Card Paypal
    We hope you will feel the same way after spending time in our Italian home. Near the ancient hill town of Volterra, surrounded by the green Tuscan countryside is our villa. Part of Borgo Collevicchi, we are on the top of a hill in the heart of Tuscany with breathtaking views of nearby valleys. This newly restored farm outbuilding contains our apartment. Our apartment is surrounded by landscaped gardens & cypress trees, all reflective of the perfect Tuscan landscape. It has all the modern amenities yet captures the Tuscan feel of architecture and design. Each of the two well appointed bedrooms has it's own air conditioner to provide comfort during the hot summer nights. To enjoy nature's gentle breezes, magnetized bug screens have been installed to allow the double doors to remain open without letting in nature's tiny creatures. Enjoy beautiful dreams on our pillow top mattresses in both bedrooms. The master bedroom features 2 extra long twin beds that can connect to form a King size bed or be enjoyed separately. The master also has an en-suite bathroom. The second bedroom has a Queen bed. The living room has a pullout queen size sofa bed. There is a second full bathroom available for guests. The kitchen features a gas stove, oven, dishwasher and full fridge. The apartment also features a washing machine with a private courtyard to air dry your laundry. The entire apartment is on the ground level and has no stairs, easy for small children or guests with mobility issues. Enjoy al fresco dining under your pergola in your private garden while savoring the panoramic views of Volterra. After dinner, enjoy a glass of wine on the outdoor couch and then take in the sunset from the pool deck. A panoramic pool makes the borgo an even more special & relaxing place after a day of sightseeing in Tuscany. The pool is open from mid June to early September and is 8 metres by 4 metres. Our property manager will greet you upon arrival, or on your first day depending on flight times/arrival time at the apartment. We feel this friendly face is an important way to start your Tuscan adventure!
  • House 4-6-7 People in Pisa

    Pisa: Duplex - upper
    • 2 BDR
    • 2 BA
    • Sleeps 7
    • #205584
    avg €111 EUR/night Paypal
    Beautiful house in duplex that can accommodate until 7 people. The apartment is at the first floor and has private access from a small garden. The large living-room/kitchen (about 30 MQ) has fully equipped kitchen with gas oven and hob, fridge and freezer, microwave and a large table where you can eat all together. The living room has a sofa and 42 "LCD TV. The sleeping area has a main bedroom with private bathroom and cabinet for clothes. The secondary bedroom has a kingsize bed and a single bed. The main bathroom is equipped with a shower and bathtub and has the washing machine. House has a terrace with a small table with chairs where you can take a branches breakfast in summer. The beds are as follows: kingsize bed in the main bedroom, a kingsize bed and a single bed in secondary bedroom, double sofa bed in living room. We can arrange you in organize visits around Tuscany. We can organize shuttle for Florence, Cinque Terre, Siena, San Gimignano, Lucca and many more. We are available to rent bicycles and to manage a shuttle service to and from the airport, the station and other destinations. Given that holds Pisa International Airport Galileo Galilei first airport in Tuscany, is an excellent reference point for people wishing to visit Tuscany because it is well connected by highway and highway to major centers of interest such as Lucca (20km, 15min) , Cinque Terre (80 KM, 70 min), Florence (70 KM, 50 min) San Gimignano (70 KM, 70 min), Siena (150km, 110 min)
  • Luxury House with Private

    Pisa: Duplex - upper
    • 2 BDR
    • 1 BA
    • Sleeps 6
    • #205583
    avg €101 EUR/night Paypal
    Luxury House, beautifully renovated with ceiling with exposed wooden beams and bricks (typical of the area) with private garden access in Pisa. The garden has a beautiful large gazebo where you can spend some time relaxing or preparing some dinner using the available outdoor barbecue. The garden has a table and chairs and foosball (soccer table). The decor has great attention to detail and carefully designed for each environment. It has all the amenities, including 42 "LCD TV, microwave, kettle, oven, washing machine, iron, hair dryer, massage shower, whirlpool bath etc.. The house is 100 square meters and consists of kitchen with island cooktop (gas burners), and large room with fireplace. The bathroom has both a shower and a bath massage. We can arrange you in organize visits around Tuscany. We can organize shuttle for Florence, Cinque Terre, Siena, San Gimignano, Lucca and many more. We are available to rent bicycles and to manage a shuttle service to and from the airport, the station and other destinations. Pisa International Airport Galileo Galilei airport in Tuscany, is an excellent reference point for people wishing to visit Tuscany because it is well connected by highway and highway to major centers of interest such as Lucca (20km, 15min) , Cinque Terre (80 KM, 70 min), Florence (70 KM, 50 min) San Gimignano (70 KM, 70 min), Siena (150km, 110 min)
  • Tuscany, Charming Vacation

    Chianni: Villa in a gated community
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #211283
    avg €107 EUR/night Paypal Pet Friendly
    The holiday home is situated in a big, fenced property with look over the roofs of the village and the Tuscan landscape. The vacation villa offers approximately 200 ms of garden to the exclusive use of the guests, with shady places under the old fruit-trees,the veranda with dining table and chairs, a shared swimming pool (4x9 m) with sunterrace, beachchairs and outside shower as well as a fantastic panorama over the Tuscan hills. The property is entirely fenced and protected by an iron gate. The picturesque, a little bit sleepy village of Rivalto with bar and grocer's shop lies at 500-m height and is surrounded by forests, vineyards and olive groves.There are numerous beautiful footpaths arround for your daily walks. In Casciana Terme, the nearby health resort (approx. 4 kms) you find a very beautifully located swimming-pool, all important services ( post, bank) , cafés, restaurants and shopping possibilities and a beautiful spa area.
  • Self Catering Apartment

    Casciana Terme: Country style house
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #152873
    avg €136 EUR/night Pet Friendly
    Comfortable accommodation in Tuscan country style, on 2 levels, it has a sunny outdoor area with umbrella, dining table, sun chairs. We do organize on demand cellars trips, horse trekking, visits to the olive-press and to nearby cellars, cooking training and dinners with all the guests of the agritourism. Convention with the Casciana Terme SPA for treatments, massages, entrance to the thermal pools.
  • Typical Stones Country

    Pisa: Country style house
    • 5 BDR
    • 3 BA
    • Sleeps 14
    • #150736
    avg €336 EUR/night Credit Card Pet Friendly
    The farmhouse on the hills of Pisa is surrounded by 42 hectares of property and features a precious private panoramic pool (6x12); in the mild weather of summer the marine breeze in the evening invites you to sit and sip your favourite drink on the poolside. For it is so conveniently located, a 30-minute car ride can take you to celebrated towns such as Volterra, San Gimignano, Monteriggioni. Florence and Pisa are only 40 km away for those beckoned by fashion, art and history. Indulging in moments of genuine pleasure is also so close, as Casciana Spa is 2 km away from the farmhouse. We can reserve guided tours around this magnificent region which the farm sets up. Daily olive tasting tours are organized as there is an olive press run by farmhouse Casciana in Chianni, Novo Frantoio. It is also possible to taste the wine of Colline Pisane and other typical products. We arrange horse trekking, kitchen training as well.
  • Self Catering Apartment

    Casciana Terme: Apartment in a complex
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #151455
    avg €86 EUR/night Credit Card Paypal Pet Friendly
  • Volterra Vacation Rental

    Volterra: Villa
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #205789
    avg €106 EUR/night Paypal Pet Friendly
  • Discovering the Hidden

    Volterra: Farmhouse
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #212698
    avg €50 EUR/night  
    In the greenest hills of the Val di Cecina , in the valley of the village of " Querceto " , the farm offers its guests a truly peaceful contact with nature, away from the bustle of the coast. Outside there is a large courtyard with table and chairs for dining out and sdraios to enjoy the cool of the countryside. There is no AIR CONDITIONING because the house is "naturally" cool even during the most torrid summer. The courtyard is in common with the only other apartment of the house and Smoking is only allowed outside the apt... Of course , paying close attention to the barn !! We suggest you to have a car , or even better a scooter/bike .... This part of Tuscany is so wonderful to visit, but has a bad public transport service. Having an your own car to move independently will allow you to discover the most hidden and enchanted many Tuscan villages , that otherwise you might not visit ! The "Val di Cecina" offers a rich calendar of musical events, art, food and wine, and in addition in Querceto, during the summer you could find a varied program of art exhibitions, concerts, shows and cultural courses. In the village, from April to August you can find the "Dispensa of the Castle", where you can buy and taste the wines and the oil of the castle, or the "La Locanda del Sole", excellent restaurant specialized in Tuscan cuisine with excellent dishes with truffles and wild boar. Take-away service and buying groceries. Around us you will find: The Etruscan spa Calidario in Venturina, where the water flows at a temperature of 35 ° C, the waterpark Acquavillage in Cecina Mare, the Cavallino Matto in Marina di Donoratico, the zoological park Gallorose in Cecina, and the acrobatic Giardino Sospeso in Riparbella. The sea is only 20/45 minutes drive from our farm, with the famous beach as Castiglioncello, Cecina, Marina di Bibbona, Donoratico and San Vincenzo with long sandy beaches, equipped or not. Cities rich in history you can visit are: Montegemoli, Montecatini Val di Cecina, Casale Marittimo, Montescudaio, Guardistallo, Bolgheri, Volterra, Suvereto, Campiglia M.Ma, Populonia, Pisa, San Gimignano, Siena, Firenze...
  • Beautiful Small Apartment

    Orciatico: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 3
    • #208536
    avg €40 EUR/night Paypal Pet Friendly
    The apartment is located on the piazza in the small medieval village of Orciatico, which is only 3 km from Lajatico, home of the famous Tenor, Andrea Bocelli. The apartment is easily accessed from the road and parking is nearby in the village. There is absolutely everything you could possibly need within the apartment which is furnished to a very good standard. All linens and towels are provided and a welcome pack on arrival for stays of four nights or more. Although there is no immediate outside area the village is very small and friendly and there are plenty of places to sit with views right across the rolling Tuscan hills. Within the village there is a bar, restaurant, two shops and an ATM machine. Pisa, Florence, Siena and the coast are all within a one hour drive and Volterra is about 20 mins. Very good, inexpensive restaurants are plentiful around the area and this part of Tuscany is rural and cheap.
  • Apartment in the Tuscan

    Volterra: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 2
    • #209569
    avg €110 EUR/night Credit Card Pet Friendly
    Querceto is a hamlet, a medieval borgo, whose nucleus is a castle around which workers' cottages have evolved (and in our family since 1543!). It's situated in the heart of the Cecina valley, between Volterra and the Etruscan Coast. Leave the car outside the walls and enter a timewarp: Querceto is a world of forgotten sounds and smells, of breathtaking views and sunsets. The apartment will charm you: they were renovated with a view to preserving the warm and welcoming style of old country houses. In the restaurant of the village you can taste delicious typical and traditional Tuscan food. The grounds (not the gardens) are yours to roam, picnic spots are close and the big swimming pool is down the steep track, surrounded by olive trees.
  • A Tuscan Style Villa

    Volterra: Villa
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #208460
    avg €125 EUR/night Paypal
    The house is 3km away from the center of the historical hill town of Volterra. It is a new building built in the traditional Tuscan style. The 1st Floor has 3 bedrooms (the main one with a walk in closet), 2 bathrooms, a kitchen, a big lounge, a balcony, patios, garden and terrace. On the ground floor a big laundry area is available.The house is built with top quality materials. The most beautiful towns in Tuscany like Siena, Pisa, Florence, San Gimignano, Livorno and many others are reachable from Volterra in about an hour.

Can't find what you are looking for? Try these nearby vacation rental regions

Chianti News and Events

The Chianti area in Tuscany is one of the most beautiful in the whole region, as well as the most well-known and appreciated by visitors from across the world.

The borders of the Chianti region are not clearly defined but in general it extends over the provinces of Florenceand Siena, covering all of the area between the two cities and extending to the east toward the Valdarno and to the west to the Val d'Elsa. The Chianti wine area extends further beyond the two cities, all around Florence and even toward Arezzo, Pistoia and Montepulciano.

You'll often find references to the "Florentine Chianti" and the "Sienese Chianti" to define the areas closest to one or the other city, but these often refer to a wine's origin within the Chianti region.

Annual Events in Chianti, Tuscany

Chianti Classico Wine Festival / Rassegna del Chianti Classico (September): This is a show case for Chianti Classico wines that takes place in Piazza Matteotti in Greve in Chianti on the second weekend of September and the preceding Thursday and Friday. You buy a glass and are then free to try any wine offered at the many stands.

Vino al Vino (September):  Chianti wine festival is held on the third weekend in September and the two preceding days in the main square of Panzano. Wine from many of the Panzano wineries is available to be sampled. This is a smaller and more informal event than the Greve wine festival in preceding week.

Discover Chianti and its beautiful towns

Only a few regions can offer such a beautiful and rich panorama as Chianti: green hills sketched by miles and miles of vineyards and olive groves, ancient walled villages, panoramic curvy roads. Chianti Classico spreads from Florence to Siena and includes the municipalities of GrevePanzano,RaddaGaiole and Castellina.

Greve in Chianti

Our trip starts in Greve in Chianti, considered by many as the gate into Chianti. This lively town is famous for its particularly shaped piazza or square that has been market place for the castles and walled villages in the surroundings since the Middle Ages.

Greve presents many different places where you can taste Chianti wine and enjoy local food. The porticos host many workshopswine bars and restaurants. One that requires mentions is the Antica Macelleria Falorni, a historical butcher shop that sells only typical products produced in Chianti. Just a few steps away stands the Wine Museum which we recommend visiting.

Panzano in Chianti

Panzano is the most populous town in Chianti and sits just a few kilometers south of Greve. Since the 12th century, Panzano played an important defensive role for Florence and its county. The Castle of Panzano was a fundamental bulwark for defending the Florentine Republic during the battles between Florence and Siena. The castle's structure can be still recognized within the older section of town including the Church of S. Maria which dates back from 1200 even if it was completely rebuilt in the 1800s in Neoclassical style.

It is really nice to wander through the old town, soaking the atmosphere of times gone by and sitting in the main square drinking a glass of Chianti wine. There are several wine bars and restaurants in Panzano that offer wine tasting while a popular place to visit is the Antica Macelleria Cecchini, a butcher shop famous for its Florentine steak where the owner recites passages from Dante's Divine Comedy while serving customers.

Castellina in Chianti

Moving towards Siena you'll reach Castellina in Chianti which dates back to the Etruscans, as attested by the Etruscan tombs of Montecalvario. Its great position in the middle of the Chianti region made Castellina a strategical headquarter between Florence and Siena. Confirming this glorious past, the massive Rocca (castle) stands proudly over the city and the impressive Via delle Volte, an underground tunnel around the city, offers breathtaking panoramic views. Walking through the small town you will notice many historical buildings that belonged to Florentine and Senese aristocracy. The Church of S. Salvatore merits a visit; rebuilt after the Second World War, the church displays a beautiful late 14th century fresco by a Tuscan master. We also recommend the Archeological Museum of Chianti Senese where many archeological findings from the Chianti region, and particularly Etruscan findings from Montecalvario, are displayed.

In Castellina you can taste wines in one of its various wine bars and the great, unforgettable taste of its many fresh and aged salami and cold cuts which have become an age-old art in Chianti and Tuscany.

Radda in Chianti

Leaving the Chiantigiana road and taking the SR429 you reach Radda in Chianti that even today preserves its original medieval look. The ancient walls still defend the center, today filled with maze-like streets. The Palazzo del Podestà overlooks the main square together with the Romanesque Church of S. Niccolò. The Palazzo was the headquarters of the League of Chianti for over four centuries, as confirmed by the many coats of arms on its facade. Just outside the center stands the ancient Franciscan Cloister of S. Maria in Prato.

It is really nice to get lost in Radda wandering around its medieval streets, drinking a glass of wine while looking at the spectacular panorama of the vineyard covered hills that surround the town.

Near Radda stands the Castle of Volpaia, an ancient walled town which we recommend visiting. The castle in sandstone has a distinctive dark color that makes it different from other castles in Chianti. In spite of the marks of the numerous wars between Florence and Siena, the main structure can easily be recognised in the massive tower and one of the minor towers. We also recommend stopping at the Commenda of S. Eufrosino, a 14th century church transformed into a wine bar. Today the Castle of Volpaia is a small tourist town where you can experience the ancient culture of wine.

Gaiole in Chianti

Not far from the Radda and the Castle of Volpaia stands Gaiole in Chianti, another town dating back to the Middle Ages. Gaiole was an important market place for the castles in the surroundings because of its position between Chianti and the Valdarno (Valley of the Arno river). Gaiole is still an important point of interest in this area. As a matter of fact, you can find many farmhouses, wine shops and wineries perfect for Chianti wine tasting and as well as lodging for your holidays.

There are many castles and fortified towns around Gaiole that deserve a visit. For example, the Castle of Vertine, the Castle of Meleto and the Pieve of Spaltenna can be visited, either through staying there during your holiday or through a special wine tasting and winery tour.
Experience the difference, no waiting
Toll Free USA, Canada
Toll Free UK
Toll Free Australia
International Rentals