Chianti Region Vacation Homes from AED 363

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

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

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 656 total

includes taxes & fees

5 Oct - 6 Oct

A garden with various plants and flowers, a pathway, and a swing set.

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

Toscana

Robert M.

AED 715 total

includes taxes & fees

4 Oct - 5 Oct

A view through a wooden door of a courtyard with stone walls and potted plants.

3. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

AED 748 total

includes taxes & fees

12 Oct - 13 Oct

A stone building with a courtyard, outdoor seating, and potted plants.

4. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

AED 1,050 total

includes taxes & fees

21 Oct - 22 Oct

A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

5. Your nest in the Tuscany countryside

Certaldo - Firenze

AED 946 total

includes taxes & fees

11 Oct - 12 Oct

A stone building with a courtyard, a table with chairs, and a wheelbarrow.

6. House with views of the Chianti

impruneta

Chase B.

AED 928 total

includes taxes & fees

14 Oct - 15 Oct

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

7. 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 1,755 total

includes taxes & fees

14 Oct - 15 Oct

A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

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

Figline Valdarno

AED 446 total

includes taxes & fees

8 Oct - 9 Oct

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Top Chianti Region Hotel Reviews

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

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

3. Chianti Craft House Badia a Passignano