Chianti Region Vacation Homes

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region holiday 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

HK$1,446 total

includes taxes & fees

14 Sept - 15 Sept

2. Apartment House with garden Tuscany Chianti , Florence 15km.

Toscana

Robert M.

HK$1,275 total

includes taxes & fees

7 Sept - 8 Sept

3. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,648 total

includes taxes & fees

8 Sept - 9 Sept

4. House with views of the Chianti

impruneta

Chase B.

HK$2,122 total

includes taxes & fees

6 Oct - 7 Oct

5. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

HK$2,359 total

includes taxes & fees

8 Sept - 9 Sept

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

Greve in Chianti

Linda L.

HK$3,287 total

includes taxes & fees

8 Sept - 9 Sept

7. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,459 total

includes taxes & fees

8 Sept - 9 Sept

8. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Figline Valdarno

HK$988 total

includes taxes & fees

8 Sept - 9 Sept

9. Your nest in the Tuscany countryside

Certaldo - Firenze

HK$2,104 total

includes taxes & fees

12 Sept - 13 Sept

10. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

HK$4,772 total

includes taxes & fees

8 Sept - 9 Sept

11. Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Certaldo

Anonymous traveller

HK$1,127 total

includes taxes & fees

7 Sept - 8 Sept

12. Blue villa surrounded by greenery between Arezzo Florence and Siena

TERRANUOVA BRACCIOLINI

HK$1,648 total

includes taxes & fees

1 Oct - 2 Oct

13. Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

Rignano sull'Arno

Anonymous traveller

HK$1,521 total

includes taxes & fees

28 Sept - 29 Sept

14. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Tavarnelle Val di Pesa

Ramona S.

HK$2,729 total

includes taxes & fees

1 Oct - 2 Oct

15. 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.

HK$4,530 total

includes taxes & fees

13 Sept - 14 Sept

16. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

HK$2,632 total

includes taxes & fees

7 Sept - 8 Sept

17. The Arch Among the Hills of Castellina

Topina

HK$2,723 total

includes taxes & fees

1 Oct - 2 Oct

18. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

HK$1,330 total

includes taxes & fees

7 Sept - 8 Sept

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

HK$3,369 total

includes taxes & fees

7 Sept - 8 Sept

20. Little cozy house

Loro Ciuffenna

HK$801 total

includes taxes & fees

8 Sept - 9 Sept

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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

10/10 Excellent

"Very nice place in the heart of Chianti Pool and premises are extraordinary"

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

10/10 Excellent

"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"

Chapter Chianti, a Member of Design Hotels

10/10 Excellent

"We had a great stay at Chapter Chianti Resort! The staff were incredibly friendly and provided excellent customer service throughout our stay. Our room was very clean and comfortable, and the air conditioning worked great, which was especially appreciated during the summer heat. The resort has really nice amenities and was very peaceful and quiet. It never felt crowded, which made it a relaxing place to stay and enjoy Chianti. We drove from Florence and it took us about an hour, so it was an easy trip and a great escape from the city. Overall, we really enjoyed our stay and would definitely recommend Chapter Chianti Resort if you’re looking for a clean, comfortable, and relaxing place to stay in the Chianti area!"

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