Chianti Region Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Chianti Region holiday rentals

Seasonal outdoor pool, pool umbrellas, pool loungers

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 HK$586
HK$699 total
includes taxes & fees
15 Jun - 16 Jun
Villa San Filippo
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (67 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 HK$1,083
HK$1,264 total
includes taxes & fees
21 Jun - 22 Jun
Villa Curina Resort
Aerial view

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
The price is HK$1,787
HK$1,983 total
includes taxes & fees
15 Jun - 16 Jun
Riserva di Fizzano Residence
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (245 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is HK$1,129
HK$1,269 total
includes taxes & fees
24 Jun - 25 Jun
Relais Villa Olmo
Property entrance

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 HK$2,256
HK$2,518 total
includes taxes & fees
23 Jun - 24 Jun
Villa il Fedino
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 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 HK$1,252
HK$1,377 total
includes taxes & fees
18 Jun - 19 Jun
Villa di Sotto
Lobby

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 HK$895
HK$984 total
includes taxes & fees
23 Jun - 24 Jun
Villa Cassia di Baccano
Outdoor dining

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 HK$1,054
HK$1,195 total
includes taxes & fees
21 Jun - 22 Jun
B&B La Fonte del Machiavelli
2 bedrooms, Frette Italian sheets, hypo-allergenic bedding, down duvets

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 HK$764
HK$867 total
includes taxes & fees
5 Jul - 6 Jul
Residence Il Connubio
Exterior

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 HK$860
HK$982 total
includes taxes & fees
24 Jun - 25 Jun
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (75 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 HK$2,463
HK$2,746 total
includes taxes & fees
15 Jun - 16 Jun
Terre di Baccio
Terrace/patio

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 HK$1,339
HK$1,491 total
includes taxes & fees
14 Jun - 15 Jun
Palazzo Pacini
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (113 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is HK$609
HK$688 total
includes taxes & fees
11 Jun - 12 Jun
Chianti Village Morrocco
Courtyard

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (167 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is HK$870
HK$1,065 total
includes taxes & fees
15 Jun - 16 Jun
I Parigi Corbinelli
Exterior

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 HK$1,179
HK$1,369 total
includes taxes & fees
9 Jul - 10 Jul
L' Eroico
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (320 reviews)
"Beautiful place for family "
Canada
Ismail
The price is HK$468
HK$542 total
includes taxes & fees
11 Jun - 12 Jun
Hu Norcenni Girasole Village
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (83 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is HK$1,311
HK$1,487 total
includes taxes & fees
30 Jun - 1 Jul
Antico Borgo il Cardino
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is HK$2,710
HK$3,053 total
includes taxes & fees
18 Jun - 19 Jun
Borgo Argenina
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.2 out of 10, Very good, (73 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is HK$419
HK$488 total
includes taxes & fees
11 Jun - 12 Jun
hu Firenze Certosa camping in town
View from property

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 HK$1,110
HK$1,438 total
includes taxes & fees
7 Jul - 8 Jul
Antica Pieve B&B
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

Palagina la cascina

Palagina la cascina

8/10 Good
"Beautiful property, rooms nice but small. Bathroom had little lighting, shower strong and hot. Would absolutely stay here again."
Alayne 1-night trip
Posted 21 hours ago
Palagina la cascina

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