Chianti Region Vacation Homes from ￥16,033

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chianti Region vacation homes

1. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

￥29,287 total

includes taxes & fees

Aug 11 - Aug 12

2. Villa with large garden in the Chianti hills

Siena

Julie H.

￥25,198 total

includes taxes & fees

Sep 1 - Sep 2

3. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

￥33,341 total

includes taxes & fees

Aug 12 - Aug 13

4. House with views of the Chianti

impruneta

Chase B.

￥40,717 total

includes taxes & fees

Aug 30 - Aug 31

5. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

￥46,013 total

includes taxes & fees

Sep 4 - Sep 5

6. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥52,144 total

includes taxes & fees

Aug 12 - Aug 13

7. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

Greve in Chianti

Linda L.

￥66,683 total

includes taxes & fees

Aug 20 - Aug 21

8. Farmhouse in Chianti

gaiole in chianti

"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...

Lara W.

￥100,425 total

includes taxes & fees

Sep 1 - Sep 2

View all properties

Find vacation rentals that suit your style

Villas

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

10/10 Excellent

"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Villa I Barronci Resort & Spa

10/10 Excellent

"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"

Salvadonica - Borgo del Chianti

10/10 Excellent

"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"

Villa Il Palagio

10/10 Excellent

"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il Palagio."

Hotel Villa Campomaggio

10/10 Excellent

"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews	133
Accommodation	417 Vacation Homes
Lowest Price	￥16,033
Highest Price	￥131,909

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region vacation homes

1. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

2. Villa with large garden in the Chianti hills