Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

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 P7,107
P7,818 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa Cassia di Baccano
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 P8,629
P9,768 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Villa il Fedino
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
The price is P29,965
P33,239 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Terre di Baccio
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 P4,860
P5,450 total
includes taxes & fees
Jan 23 - Jan 24, 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
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
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 P10,059
P11,618 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rocca di Castagnoli
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
I Parigi Corbinelli
Exterior
Sportland

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
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 P5,344
P7,538 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Antica Pieve B&B
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)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
Chianti Village Morrocco
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
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 P7,796
P8,783 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
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 P9,011
P10,189 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
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 P7,129
P8,257 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Casa Vacanze Squarcialupi
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

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 1 month ago
Hotel Borgo di Cortefreda Relais

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