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.

Rental Amenities

Accessibility

Bedrooms

Total Rent

From 
To 

Rental Payment

Activities

Ski-Out
Ski-In    
Walk only

Waterfront
Water within
Walk only

Golf
View Map

Chianti Vacation Activities

10 Vacation Rentals

Your Favs ()
view Tile View List View
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.

  • Tuscany, Charming Vacation

    Chianni: Villa in a gated community
    2 BDR • 1 Loft • 1 Den • 2 BA • Sleeps 6 • #211283
    95 to 127 EUR/night
    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.
  • A Cottage in Delightful

    Chianni: Cottage
    3 BDR • 2 BA • Sleeps 6 • #239417
    136 to 164 GBP/night
    Set in the Pisan Hills - a delightful part of Tuscany, Chianni, is an idyllic spot for a holiday or to celebrate a special occasion. In a panoramic position on a hillside affording breathtaking views of the Tuscan landscape, Villa Adelina is just five minutes walk from the little hill town of Chianni, which boasts three good restaurants and a couple of bars where you can have a drink and engage with the locals. This is unspoilt Tuscany at its most charming, yet it is only 40 minutes drive from Pisa Airport. The Villa itself is available for rental as Property ID 239409 and will accommodate 12 people. This cottage is in the grounds of the Villa and will accommodate just 6 people. It is therefore ideal for smaller parties or as an overspill facility for parties of up to 18. The cottage is a more rustic building but has been recently modernized and has a luxurious master bedroom and ensuite bathroom. There are also two further bedrooms - one double and one twin. Our policy is not to rent both properties to different groups at the same time, but only to rent out the cottage when there is not a party using the Villa. We believe the cottage may be of particular interest out of season when families or smaller parties wish to explore Tuscany. Chianni is a great centre from which to explore the art of Tuscany. Visible from the cottage on a rocky promontory is the ancient city of Volterra famously written about by D H Lawrence in Etruscan Places. Also within a short drive is the magnificent San Gimignano - whose towers can be considered the first skyscapers. Florence, Lucca and Siena can be reached in an hour and a half. The Pisan Hills Wine Route (Strada del Vino) runs through Chianni and takes in a number of other delightful places such as Lari, Terriciola, and Palaia. There are wine producers and vendors within a short distance of the villa. The beautiful spa town of Casciana Terme is just 7 km from Chianni and there you can enjoy a variety of massages and spa treatments which can be booked in advance. It also boasts one of the best ice cream parlours in Tuscany. Tuscany is a great place for a cycling holiday. Use The cottage as your base and we can put you in touch with firms from whom you can hire bikes from average to high specification. The cottage has been designed for comfortable living. There is an efficient central heating system for use outside the peak summer season and it provides hot water on demand. The sitting room is furnished with comfortable sofas and a TV and DVD system. The dining table will seat 6 people in comfort and there is a table on the terrace for alfresco meals. The kitchen is fully equipped with cooking utensils, crockery and cutlery. There is a large fridge-freezer, oven, microwave, gas hob and dishwasher. The laundry room has washer-drier, iron and ironing-board and large sink. The bedrooms are equipped with comfortable beds with bedside tables and lamps, wardrobes and in some cases chests of drawers. All bathrooms are equipped with washbasin, shower, wc and bidet. There are sets of towels for each guest as well separate towels for use at the swimming pool.
  • Elegant Villa in

    Chianni: Villa
    6 BDR • 5 BA • Sleeps 12 • #239409
    271 to 357 GBP/night
    Set in the Pisan Hills - a delightful part of Tuscany, our Villa, in Chianni, is an idyllic spot for a holiday or to celebrate a special occasion. In a panoramic position on a hillside affording breathtaking views of the Tuscan landscape, the Villa is just five minutes walk from the little hill town of Chianni, which boasts three good restaurants and a couple of bars where you can have a drink and engage with the locals. This is unspoilt Tuscany at its most charming, yet it is only 40 minutes drive from Pisa Airport. Built in the Liberty style, the villa, which will accommodate up to 12 people, has been completely restored with modern conveniences, but retains its original elegance and spendour as well as many original pieces of Tuscan furniture and art. It is set in olive groves and there is a beautiful garden with tall trees that provide welcome shade during summer months. The large sitting room and dining room on the south side of the villa open on to a terrace with a long table and chairs for alfresco dining, and there is a smaller patio adjacent to the kitchen. There is a large swimming pool (12m x 6m) which enjoys the sunshine all day, and there are ombrelloni to shelter under while you enjoy a drink or snack. The pool has Roman steps and a diving board as well as lights so that it can be used for midnight swims. Chianni is a great centre from which to explore the art of Tuscany. Visible from the villa on a rocky promontory is the ancient city of Volterra famously written about by D H Lawrence in Etruscan Places. Also within a short drive is the magnificent San Gimignano - whose towers can be considered the first skyscapers. Florence, Lucca and Siena can be reached in an hour and a half. The Pisan Hills Wine Route (Strada del Vino) runs through Chianni and takes in a number of other delightful places such as Lari, Terriciola, and Palaia. There are wine producers and vendors within a short distance of the villa. The beautiful spa town of Casciana Terme is just 7 km from Chianni and there you can enjoy a variety of massages and spa treatments which can be booked in advance. It also boasts one of the best ice cream parlours in Tuscany. Tuscany is a great place for a cycling holiday if you are a keen cyclist - there are plenty of hills. Use the Villa as your base and we can put you in touch with firms from whom you can hire bikes from average to high specification. The Villa has been designed for comfortable living. There is an efficient central heating system for use outside the peak summer season and it provides hot water whenever needed. The sitting room is furnished with large comfortable sofas and a TV and DVD system. The dining table will seat 12 people in comfort and there is another 12 man table outside on the terrace if you want to dine outside. The kitchen is fully equipped with cooking utensils, crockery and cutlery. There is a large fridge-freezer, oven, microwave, gas hob and dishwasher. There is a kitchen table which seats six. The laundry room has washer-drier, iron and ironing-board and large sink. The bedrooms are all equipped with comfortable beds with bedside tables and lamps, large wardrobes and in some cases dressing tables. All bathrooms are equipped with washbasin, shower/bath, wc and bidet. There are sets of towels for each guest as well separate towels for use at the swimming pool. ***********If the group is larger than 12, the Owners do have another property on site ID 239417 that can accommodate an additional 6 occupants. Please check with us if the property is available for your time period***************
  • Peaceful Tuscan Retreat in

    Orciatico: Apartment
    1 BDR • 1 BA • Sleeps 2 • #208536
    40 to 40 EUR/night
    Breathtaking views await you in the beautiful medieval village of Orciatico . Completely surrounded by nature this is a unique opportunity to experience living like an Italian. Meander around the streets and be warmly greeted by the locals, many of whom have lived here all their lives. Florence, Pisa, Sienna, Volterra and the coast are easily reached within an hour and what better than to spend a day in the city then return to peace, tranquility. Within the apartment there is a wall safe, fridge, toaster, coffee maker, kettle, full oven and hob. Tea, coffee and sugar are provided. All bed linen and towels included. Large range of DVDs, CDs. Books and games. Plenty of local tourist information This is a typical small Italian village with only one shop, one bar and from Easter until September one restaurant. The nearest large supermarket is about 10 kms. There are more smaller shops in Lajatico which is 5 km
  • Gorgeous Views of Volterra

    Volterra: Apartment in a villa
    2 BDR • 2 BA • Sleeps 6 • #224210
    180 to 250 EUR/night
    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 mid 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!
  • Volterra Vacation Rental

    Volterra: Villa
    3 BDR • 2 BA • Sleeps 6 • #205789
    80 to 130 EUR/night
  • An Exclusive Sea View

    Castellina Marittima: Villa in a gated community
    7 BDR • 9 BA • Sleeps 14 • #234535
    556 to 556 EUR/night  
    This is a unique country house on a winery in the Tuscan Hills in front of the Tyrrhenian Sea. It can accommodate up to 14 people. There are 7 ensuite bedrooms. This is a place perfect for finding peace and quiet. The house is on a winery that makes a famous Tuscan IGT, we are 20 minutes from Bolgheri, 10 minutes from the Highway and 40 minutes from Pisa Airport. You can visit Florence,Pisa and Lucca very easily from where we are. There are two nearby ports where you can rent a boat and sail to nearby Elba Island. There are renowned restaurants and wineries within minutes. Everything you expect in a vacation you can have here with us. We speak English, Italian, French and German.
  • Self Catering Apartment

    Casciana Terme: Country style house
    2 BDR • 2 BA • Sleeps 6 • #152873
    125 to 148 EUR/night
    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.
  • Self Catering Apartment

    Casciana Terme: Apartment in a complex
    1 Loft • 1 Den • 1 BA • Sleeps 4 • #151455
    80 to 100 EUR/night
  • Apartment in the Tuscan

    Volterra: Apartment
    1 BDR • 1 BA • Sleeps 2 • #209569
    80 to 110 EUR/night
    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.

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
www.chianti.com/traveling-through-chianti.html

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
1.888.869.6377
Toll Free UK
0.800.249.4265
Toll Free Australia
1.800.150.197
International Rentals
1.250.469.9543