Chianti Region Vacation Homes from AED 374

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 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

AED 684 total

includes taxes & fees

1 Sep - 2 Sep

2. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Toscana

Kim

AED 919 total

includes taxes & fees

2 Sep - 3 Sep

3. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

AED 779 total

includes taxes & fees

6 Sep - 7 Sep

4. Villa with large garden in the Chianti hills

Siena

Julie H.

5. House with views of the Chianti

impruneta

Chase B.

AED 987 total

includes taxes & fees

1 Sep - 2 Sep

6. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

AED 1,098 total

includes taxes & fees

4 Sep - 5 Sep

7. Fornace di Bonazza - wonderful house among the Chianti hills

Barberino Tavarnelle

Anonymous traveler

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

Greve in Chianti

Linda L.

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

Figline Valdarno

AED 468 total

includes taxes & fees

28 Sep - 29 Sep

10. Casa Marisa in Castellina in Chianti

Castellina in Chianti

AED 1,251 total

includes taxes & fees

9 Sep - 10 Sep

11. 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.

AED 2,230 total

includes taxes & fees

8 Sep - 9 Sep

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

Certaldo

Anonymous traveler

AED 526 total

includes taxes & fees

2 Sep - 3 Sep

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

Rignano sull'Arno

Anonymous traveler

AED 711 total

includes taxes & fees

28 Sep - 29 Sep

14. 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.

AED 2,142 total

includes taxes & fees

1 Sep - 2 Sep

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

BARBERINO TAVARNELLE

Ramona S.

AED 1,275 total

includes taxes & fees

1 Oct - 2 Oct

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

Montevarchi

AED 1,230 total

includes taxes & fees

1 Sep - 2 Sep

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

Montespertoli

AED 621 total

includes taxes & fees

1 Sep - 2 Sep

18. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Rosennano

AED 1,418 total

includes taxes & fees

14 Sep - 15 Sep

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

Castelnuovo Berardenga

Anonymous traveler

AED 1,574 total

includes taxes & fees

1 Sep - 2 Sep

20. Little cozy house

Loro Ciuffenna

AED 374 total

includes taxes & fees

2 Sep - 3 Sep

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Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

10/10 Excellent

"Great place."

"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!!"

Castello di Tornano Wine Resort

8/10 Good

"We really like this place. Pool was very nice and staff were mostly helpful. Its a pretty good location to visit multiple areas as well. Room air conditioner did an ok job upstairs in bedroom loft but struggled to keep it cool in the sitting area on main level. The view from the tower is awesome but its a climb"

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. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

3. Chianti Craft House Badia a Passignano