Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Chianti Region vacation rentals

Lobby lounge
Villa Cassia di Baccano

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ₩212,575
₩233,832 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Cassia di Baccano
Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, blackout drapes
Terre di Baccio

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
Exterior detail
Villa il Fedino

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ₩215,368
₩243,809 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa il Fedino
Property amenity
Antica Pieve B&B

Townhouse in Barberino Tavarnelle

Antica Pieve B&B
9.4 out of 10, Exceptional, (14)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is ₩133,374
₩188,142 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Antica Pieve B&B
Front of property
L' Eroico

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Aparthotel in Figline e Incisa Valdarno

Relais Villa Belvedere
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is ₩124,305
₩139,324 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Relais Villa Belvedere
Terrace/patio
B&B La Fonte del Machiavelli

Townhouse in San Casciano in Val di Pesa

B&B La Fonte del Machiavelli
9.2 out of 10, Wonderful, (82)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ₩178,885
₩203,677 total
includes taxes & fees
Dec 18 - Dec 19
B&B La Fonte del Machiavelli
Seasonal outdoor pool
Agriturismo La Ferrozzola

Vacation Home in Castellina in Chianti

Agriturismo La Ferrozzola
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno

Townhouse in Castellina in Chianti

Residenzia del Sogno
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ₩203,988
₩231,294 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Residenzia del Sogno
Full-size fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

Residence in Impruneta

Rocca Palazzaccio
3.0 star property
9.0 out of 10, Wonderful, (14)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
Rocca Palazzaccio
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Residence in Loro Ciuffenna

Relais Villa Belpoggio - Residenza d'Epoca
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is ₩243,222
₩267,542 total
includes taxes & fees
Dec 17 - Dec 18
Relais Villa Belpoggio - Residenza d'Epoca
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

Townhouse in Barberino Tavarnelle

La Locanda di Pietracupa
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Apartment in Castellina in Chianti

Casa Vacanze Squarcialupi
8.0 out of 10, Very Good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ₩177,942
₩206,092 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Casa Vacanze Squarcialupi
Outdoor pool, sun loungers
I Parigi Corbinelli

Townhouse in Florence

I Parigi Corbinelli
9.4 out of 10, Exceptional, (162)
"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."
Australia
Tim
The price is ₩113,036
₩145,053 total
includes taxes & fees
Dec 17 - Dec 18
I Parigi Corbinelli
Outdoor pool, sun loungers
Rocca di Castagnoli

Townhouse in Gaiole in Chianti

Rocca di Castagnoli
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is ₩353,070
₩402,177 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Rocca di Castagnoli
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

Residence in Barberino Tavarnelle

Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
Front of property
Borgo Antico Residence

Apartment in Certaldo Alto

Borgo Antico Residence
10.0 out of 10, Exceptional, (3)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is ₩130,911
₩192,332 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Borgo Antico Residence
Exterior
Sportland

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Terrace/patio
Casa Vacanze Le Fornaci

Apartment in Pergine Valdarno

Casa Vacanze Le Fornaci
9.4 out of 10, Exceptional, (3)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is ₩194,581
₩219,212 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Casa Vacanze Le Fornaci
Interior
Residence Il Connubio

Residence in Impruneta

Residence Il Connubio
3.0 star property
8.8 out of 10, Excellent, (32)
"Such a cute little place! Very clean and easy to get around! Would highly recommend!"
United States
Desiree
Residence Il Connubio
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

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"
Andrea 2-night trip
Posted 8 days ago
Castello di Fonterutoli Wine Resort

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