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

Chianti Region Vacation Rentals

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Our top choices for Chianti Region vacation rentals

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
The price is P4,962
P5,877 total
includes taxes & fees
Jul 2 - Jul 3
Villa San Filippo

Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is P6,681
P7,489 total
includes taxes & fees
Jul 16 - Jul 17
Borgo di Erboli

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (69 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is P10,450
P12,054 total
includes taxes & fees
Jun 28 - Jun 29
Villa Curina Resort

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is P9,708
P10,679 total
includes taxes & fees
Jul 1 - Jul 2
Villa Cassia di Baccano

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
9.2 out of 10, Wonderful, (27 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 P6,947
P7,921 total
includes taxes & fees
Jul 11 - Jul 12
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

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 P16,651
P18,595 total
includes taxes & fees
Jun 29 - Jun 30
Villa il Fedino

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (32 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
Riserva di Fizzano Residence

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (34 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is P10,438
P11,482 total
includes taxes & fees
Jul 5 - Jul 6
Villa di Sotto

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (247 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is P11,770
P13,156 total
includes taxes & fees
Jul 22 - Jul 23
Relais Villa Olmo

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is P4,492
P5,081 total
includes taxes & fees
Jul 6 - Jul 7
Chianti Village Morrocco

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is P5,254
P6,617 total
includes taxes & fees
Jun 29 - Jun 30
I Parigi Corbinelli

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is P8,138
P9,231 total
includes taxes & fees
Jun 28 - Jun 29
B&B La Fonte del Machiavelli

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 P9,296
P10,365 total
includes taxes & fees
Jul 10 - Jul 11
Palazzo Pacini

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
9.0 out of 10, Wonderful, (34 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
The price is P5,890
P6,688 total
includes taxes & fees
Jul 19 - Jul 20
Residence Il Connubio

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (76 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is P19,016
P21,197 total
includes taxes & fees
Jun 28 - Jun 29
Terre di Baccio

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is P3,080
P3,528 total
includes taxes & fees
Jul 5 - Jul 6
Sportland

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 P5,726
P6,578 total
includes taxes & fees
Jul 1 - Jul 2
Mariani Bed & Breakfast

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (321 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is P4,597
P5,266 total
includes taxes & fees
Jul 8 - Jul 9
Hu Norcenni Girasole Village

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is P9,098
P10,566 total
includes taxes & fees
Jul 1 - Jul 2
L' Eroico

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.6 out of 10, Excellent, (64 reviews)
"Very friendly staff. Great breakfast! In alla very nice!"
Sweden
martin
The price is P5,600
P6,440 total
includes taxes & fees
Jul 28 - Jul 29
Villa Il Palagio
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