Chianti Region Vacation Rentals

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Our top choices for Chianti Region vacation rentals

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is P10,795
P12,153 total
includes taxes & fees
Mar 29 - Mar 30
Villa il Fedino

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"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
The price is P9,835
P11,375 total
includes taxes & fees
Mar 31 - Apr 1
L' Eroico

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.4 out of 10, Exceptional, (162 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is P4,535
P5,823 total
includes taxes & fees
Mar 29 - Mar 30
I Parigi Corbinelli

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is P10,665
P12,287 total
includes taxes & fees
Apr 7 - Apr 8
Villa Curina Resort

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (28 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is P10,186
P11,205 total
includes taxes & fees
Mar 29 - Mar 30
Villa di Sotto

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is P6,304
P7,213 total
includes taxes & fees
Apr 17 - Apr 18
Mariani Bed & Breakfast

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.0 out of 10, Very Good, (60 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
The price is P2,867
P3,362 total
includes taxes & fees
Apr 1 - Apr 2
hu Firenze Certosa camping in town

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is P3,072
P3,518 total
includes taxes & fees
Mar 29 - Mar 30
Sportland

Certaldo

Certaldo
4.0 star property
Certaldo Alto
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful property, amazing views, perfectly cleaned, attentive and kind management"
United States
sandro
Certaldo

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is P7,508
P8,607 total
includes taxes & fees
Apr 26 - Apr 27
Antico Borgo il Cardino

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 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is P7,223
P8,224 total
includes taxes & fees
Mar 29 - Mar 30
B&B La Fonte del Machiavelli

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (229 reviews)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
United States
Cameron
The price is P7,394
P8,343 total
includes taxes & fees
Mar 30 - Mar 31
Relais Villa Olmo

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"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 P7,584
P10,011 total
includes taxes & fees
Apr 16 - Apr 17
Antica Pieve B&B

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is P6,030
P6,772 total
includes taxes & fees
Apr 19 - Apr 20
Palazzo Pacini

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (40 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
The price is P5,849
P6,851 total
includes taxes & fees
Apr 1 - Apr 2
Villa San Filippo

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.4 out of 10, Exceptional, (25 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is P6,455
P7,379 total
includes taxes & fees
Apr 10 - Apr 11
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (32 reviews)
"Such a cute little place! Very clean and easy to get around! Would highly recommend!"
United States
Desiree
The price is P4,911
P5,612 total
includes taxes & fees
Mar 29 - Mar 30
Residence Il Connubio

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is P4,529
P5,121 total
includes taxes & fees
Mar 29 - Mar 30
Chianti Village Morrocco

Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is P4,562
P6,969 total
includes taxes & fees
Mar 29 - Mar 30
Borgo Antico Residence

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is P10,567
P12,180 total
includes taxes & fees
Mar 31 - Apr 1
Borgo Argenina
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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