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

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chianti Region condo rentals

A narrow stone corridor with a brick floor, a metal gate, and a brick archway leading to another room.

1. Il Frantoio delle Grazie

Il Frantoio delle Grazie
Florence
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place, picturesque country setting. Next time we stay here we will consider renting a car. The walk to the bus or train is only about a mile and it wasn’t too hot out. The kids really enjoyed the pool."
United States
Emily
The price is ￥16,885
￥34,186 total
includes taxes & fees
Nov 7 - Nov 8
Il Frantoio delle Grazie
A bedroom with a large bed, a nightstand, a wooden cabinet, a window with a view, and a painting on the wall.

2. Annettas house

Annettas house
Historic Centre of Florence
The price is ￥14,010
￥19,476 total
includes taxes & fees
Dec 1 - Dec 2
Annettas house
A hotel room with a large bed, a TV, a desk with a chair, a stone wall, and a window with a view.

3. Oriuolo 5

Oriuolo 5
Historic Centre of Florence
The price is ￥16,732
￥30,186 total
includes taxes & fees
Nov 23 - Nov 24
Oriuolo 5
A green double door with ornate handles, a metal grille above, and a plaque on the wall to the right.

4. Superior Sant'Ambrogio Room with Private Bath

Superior Sant'Ambrogio Room with Private Bath
Historic Centre of Florence
The price is ￥12,835
￥18,462 total
includes taxes & fees
Nov 12 - Nov 13
Superior Sant'Ambrogio Room with Private Bath
A modern bedroom with a large bed, a bedside table, and a chair.

5. Tiny Private Room Steps from the Duomo

Tiny Private Room Steps from the Duomo
Historic Centre of Florence
The price is ￥14,594
￥16,704 total
includes taxes & fees
Nov 4 - Nov 5
Tiny Private Room Steps from the Duomo
A modern hotel room with a large bed, a desk, and a chair. There is a mirror on the wall and a ceiling light fixture.

6. AC, Washer+Dryer, WiFi - Elegant Apartment In The Noblest District of Florence,

AC, Washer+Dryer, WiFi - Elegant Apartment In The Noblest District of Florence,
Historic Centre of Florence
9.6 out of 10, Exceptional, (25 reviews)
"The host was very helpful at check-in and the apartment was clean and convenient."
United States
Sara G.
The price is ￥31,649
￥61,892 total
includes taxes & fees
Nov 18 - Nov 19
AC, Washer+Dryer, WiFi - Elegant Apartment In The Noblest District of Florence,
A view through an arched window of a historic building with a prominent bell tower and a dome.

7. King Suite - Michelangelo

King Suite - Michelangelo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (2 reviews)
"The property is in a perfect location for exploring the city. The accommodation was clean and comfortable. The host was extremely helpful in identifying parking, restaurants and sights. We would definitely recommend this property. To be noted: there is no elevator and while this apartment was on the first floor, others may face a climb. "
United States
Christine G.
The price is ￥100,736
￥118,055 total
includes taxes & fees
Nov 5 - Nov 6
King Suite - Michelangelo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chianti Region Hotel Reviews

Borgo Vescine

Borgo Vescine

10/10 Excellent
"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"
James 2-night trip
Posted 2 days ago
Borgo Vescine

Find out more about Chianti Region

Chianti Region Condo Rentals information

Number of reviews
10
Accommodation
1 Condo Rentals
Lowest Price
￥16,704
Highest Price
￥61,892