Chianti Region Vacation Rentals

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Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Chianti Region holiday rentals

Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is RM592
RM652 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano
Premium bedding, down duvets, in-room safe, blackout curtains
Terre di Baccio

Terre di Baccio

Terre di Baccio
Greve in Chianti
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

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is RM600
RM679 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa il Fedino
Property amenity
Antica Pieve B&B

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
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 RM372
RM524 total
includes taxes & fees
10 Jan - 11 Jan 2026
Antica Pieve B&B
Front of property
L' Eroico

L' Eroico

L' Eroico
Gaiole in Chianti
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

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is RM429
RM479 total
includes taxes & fees
14 Dec - 15 Dec
Relais Villa Belvedere
Terrace/patio
B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
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 RM500
RM569 total
includes taxes & fees
15 Dec - 16 Dec
B&B La Fonte del Machiavelli
Seasonal outdoor pool
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
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, pool loungers
Residenzia del Sogno

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
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
Residenzia del Sogno
Full-sized fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
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

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
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 RM678
RM746 total
includes taxes & fees
14 Dec - 15 Dec
Relais Villa Belpoggio - Residenza d'Epoca
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
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 RM496
RM574 total
includes taxes & fees
15 Dec - 16 Dec
Casa Vacanze Squarcialupi
Outdoor pool, pool loungers
I Parigi Corbinelli

I Parigi Corbinelli

I Parigi Corbinelli
Florence
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 RM316
RM405 total
includes taxes & fees
17 Dec - 18 Dec
I Parigi Corbinelli
Outdoor pool, pool loungers
Rocca di Castagnoli

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
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
Rocca di Castagnoli
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
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

Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
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 RM365
RM536 total
includes taxes & fees
2 Jan - 3 Jan 2026
Borgo Antico Residence
Exterior
Sportland

Sportland

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

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
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 RM542
RM611 total
includes taxes & fees
14 Dec - 15 Dec
Casa Vacanze Le Fornaci
Interior
Residence Il Connubio

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
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 5 days ago
Castello di Fonterutoli Wine Resort

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