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Featured Villas in Chianti Region

Villa con Piscina, Sauna, Jacuzzi

10.0 out of 10, Exceptional, (1)
"Beautiful property, highly recommended. "
The price is AU$1,128
includes taxes & fees
17 Sept - 18 Sept
Villa con Piscina, Sauna, Jacuzzi

Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

9.8 out of 10, Exceptional, (21)
"We staid there for a week, great with kids (pool) and good location in the countryside if you have car (30m from Florence, 15m from San Gimignano, 35 from Siena)"
The price is AU$1,079
includes taxes & fees
6 Sept - 7 Sept
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

10.0 out of 10, Exceptional, (3)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
The price is AU$714
includes taxes & fees
20 Aug - 21 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

10.0 out of 10, Exceptional, (1)
The price is AU$5,537
includes taxes & fees
16 Sept - 17 Sept
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is AU$3,164
includes taxes & fees
24 Aug - 25 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Villa Cicogna Private Villa, sleeps 2 -10 guests

10.0 out of 10, Exceptional, (6)
"Our family stayed here for a local wedding and enjoyed the charm of this quiet town and comfortable villa. The hosts were super responsive and welcoming, making sure we had everything we needed for a pleasant stay. Our toddler loved running around and swimming every day in the pool. The location is perfect to drive to nearby cities with parking provided. Would love to visit again!"
The price is AU$233
includes taxes & fees
19 Sept - 20 Sept
Villa Cicogna Private Villa, sleeps 2 -10 guests

Beautiful Tuscan home between Florence & Siena

10.0 out of 10, Exceptional, (5)
"Property was just as listed. Clean, large, and a great location for wine tasting, local restaurants, and more. The owners were super helpful in planning some local outings. Highly recommended. "
The price is AU$3,621
includes taxes & fees
24 Aug - 25 Aug
Beautiful Tuscan home between Florence & Siena

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is AU$11,591
includes taxes & fees
29 Aug - 30 Aug
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi

9.4 out of 10, Exceptional, (3)
"Beautiful stay in a wonderful Italian villa. "
The price is AU$852
includes taxes & fees
3 Sept - 4 Sept
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi

10.0 out of 10, Exceptional, (1)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
The price is AU$3,258
includes taxes & fees
30 Aug - 31 Aug
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

10.0 out of 10, Exceptional, (12)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
The price is AU$3,748
includes taxes & fees
6 Sept - 7 Sept
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Villa Gabriella Chianti Toscana

Villa Gabriella Chianti Toscana

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

10.0 out of 10, Exceptional, (1)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
The price is AU$3,715
includes taxes & fees
4 Sept - 5 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
The price is AU$1,465
includes taxes & fees
21 Aug - 22 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

Villa 'Country house Sofia Villas' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Country house Sofia Villas' with Private Pool, Wi-Fi and Air Conditioning

Exclusive Villa with Concierge service and heated pool on the Florentine hills

10.0 out of 10, Exceptional, (103)
"Our host (Cate), along with her sister and mother, were fantastic. Very responsive, easy to get ahold of and worked very hard to ensure our visit was amazing. Cate was onsite and worked closely with the catering company and made sure all went well.."
The price is AU$2,668
includes taxes & fees
3 Sept - 4 Sept
Exclusive Villa with Concierge service and heated pool on the Florentine hills

Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

The price is AU$3,688
includes taxes & fees
13 Sept - 14 Sept
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

The price is AU$3,043
includes taxes & fees
29 Aug - 30 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Vanna - Certaldo' with Garden & Wi-Fi

The price is AU$1,205
includes taxes & fees
2 Sept - 3 Sept
Villa 'Vanna - Certaldo' with Garden & Wi-Fi

Villa Il Signorino

10.0 out of 10, Exceptional, (2)
"Nice place 👌 "
The price is AU$922
includes taxes & fees
2 Sept - 3 Sept
Villa Il Signorino
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

Frequently asked questions

How much do villas in Chianti Region cost?
Prices for villas in Chianti Region range between AU$3,164 and AU$3,164 per night. No matter your budget, you're sure to find a place that fits your needs on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Chianti Region?
Chianti Region has 495 villas to pick from. Enter your travel dates and destination and organise your perfect stay today.
What is there to do near my villa in Chianti Region?
One of the most important travel accessories for your Chianti Region adventure is an epic itinerary! Colle di Val dElsa Cathedral, Sentierelsa Trail and Piazza Arnolfo di Cambio are some of the top sights if you're visiting Val dElsa. San Gimignano is also home to fantastic attractions, such as Sovestro in Poggio Winery. Eager to add to your to-do list? Drop by Museo Civico and Museum San Gimignano 1300 too.