Chianti Region Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Chianti Region holiday rentals

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$2,243
HK$2,504 total
includes taxes & fees
4 Jul - 5 Jul
Villa il Fedino
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$1,209
HK$1,357 total
includes taxes & fees
8 Jul - 9 Jul
Relais Villa Olmo
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$1,344
HK$1,479 total
includes taxes & fees
5 Jul - 6 Jul
Villa di Sotto
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$2,449
HK$2,730 total
includes taxes & fees
24 Jun - 25 Jun
Terre di Baccio
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$1,839
HK$2,041 total
includes taxes & fees
2 Jul - 3 Jul
Riserva di Fizzano Residence
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$2,391
HK$2,702 total
includes taxes & fees
23 Jun - 24 Jun
Borgo Argenina
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$1,304
HK$1,453 total
includes taxes & fees
3 Jul - 4 Jul
Palazzo Pacini
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (68 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 HK$1,346
HK$1,552 total
includes taxes & fees
23 Jun - 24 Jun
Villa Curina Resort
Garden view

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$580
HK$692 total
includes taxes & fees
26 Jun - 27 Jun
Villa San Filippo
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$855
HK$976 total
includes taxes & fees
4 Jul - 5 Jul
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
View from room

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 HK$623
HK$703 total
includes taxes & fees
28 Jun - 29 Jun
Chianti Village Morrocco
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, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is HK$1,048
HK$1,189 total
includes taxes & fees
22 Jun - 23 Jun
B&B La Fonte del Machiavelli
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$1,087
HK$1,196 total
includes taxes & fees
24 Jun - 25 Jun
Villa Cassia di Baccano
Front of property

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is HK$1,381
HK$1,519 total
includes taxes & fees
28 Jun - 29 Jun
Relais Villa Belpoggio - Residenza d'Epoca
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, (33 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
The price is HK$728
HK$828 total
includes taxes & fees
5 Jul - 6 Jul
Residence Il Connubio
Lounge

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 HK$737
HK$847 total
includes taxes & fees
25 Jun - 26 Jun
Mariani Bed & Breakfast
Exterior

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
Hu Norcenni Girasole Village
View from room

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.6 out of 10, Exceptional, (5 reviews)
"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 HK$1,111
HK$1,249 total
includes taxes & fees
22 Jun - 23 Jun
Casa Vacanze Le Fornaci
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$1,303
HK$1,479 total
includes taxes & fees
3 Jul - 4 Jul
Antico Borgo il Cardino
Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, pool loungers

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.6 out of 10, Excellent, (63 reviews)
"Very friendly staff. Great breakfast! In alla very nice!"
Sweden
martin
The price is HK$720
HK$828 total
includes taxes & fees
2 Jul - 3 Jul
Villa Il Palagio
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

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"My husband and I recently stayed at this beautiful resort and spa to celebrate our 46th wedding anniversary, and it was truly a memorable experience from beginning to end. The staff was exceptionally kind, welcoming, and helpful, making us feel valued throughout our stay. The food was absolutely delicious, with every meal exceeding our expectations. One of the highlights of our visit was the relaxing couple's massage, which left us feeling refreshed and rejuvenated. The resort amenities were wonderful and thoughtfully maintained, providing everything needed for a peaceful and enjoyable getaway. The views were simply magnificent, and each evening we were captivated by the mesmerizing sunsets that painted the sky with stunning colors. We also enjoyed exploring the nearby town, which was charming and beautiful. Between the breathtaking scenery, outstanding service, luxurious amenities, and tranquil atmosphere, our anniversary celebration was everything we had hoped for and more. We highly recommend this resort and spa to anyone looking for a relaxing and unforgettable escape. We look forward to returning again someday."
Maria 5-night trip
Posted 4 hours ago
Villa I Barronci Resort & Spa

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