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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$1,061
includes taxes & fees
3 Nov - 4 Nov
Villa con Piscina, Sauna, Jacuzzi

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$2,578
includes taxes & fees
3 Nov - 4 Nov
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

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

10.0 out of 10, Exceptional, (38)
"Our family of 17 stayed at a villa near Montespertoli. In fact the villa also was a winery and olive oil producer. Nicola was the host as well as the owner. He was available for everyone of our guest. Requests from laundry to suggestions for restaurants, to taxi services to Florence...Nicola was always available to take care of us. I couldn't have asked for a more perfect venue and host."
The price is AU$3,603
includes taxes & fees
8 Oct - 9 Oct
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Villino Tre Pini with private pool in Florence by TuscanyWeGo

The price is AU$1,075
includes taxes & fees
5 Oct - 6 Oct
Villino Tre Pini with private pool in Florence by TuscanyWeGo

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

The price is AU$437
includes taxes & fees
2 Nov - 3 Nov
Villa Il Frantoio 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$2,773
includes taxes & fees
16 Oct - 17 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is AU$11,460
includes taxes & fees
5 Oct - 6 Oct
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

Beautiful Tuscan home between Florence & Siena

10.0 out of 10, Exceptional, (6)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
The price is AU$2,979
includes taxes & fees
12 Oct - 13 Oct
Beautiful Tuscan home between Florence & Siena

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

10.0 out of 10, Exceptional, (1)
The price is AU$3,758
includes taxes & fees
6 Oct - 7 Oct
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

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

The price is AU$2,754
includes taxes & fees
1 Nov - 2 Nov
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

"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$1,525
includes taxes & fees
7 Oct - 8 Oct
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

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$720
includes taxes & fees
13 Oct - 14 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

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

The price is AU$1,036
includes taxes & fees
6 Oct - 7 Oct
Villa 'Vanna - Certaldo' with Garden & Wi-Fi

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$3,128
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa Il Signorino

10.0 out of 10, Exceptional, (2)
"Nice place 👌 "
The price is AU$799
includes taxes & fees
5 Oct - 6 Oct
Villa Il Signorino

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
The price is AU$2,330
includes taxes & fees
8 Oct - 9 Oct
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

DEP. FONATNELLA x2+2 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona

The price is AU$601
includes taxes & fees
5 Oct - 6 Oct
DEP. FONATNELLA x2+2 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona

Wedding Villa in Chianti - Villa la Veronica

The price is AU$3,452
includes taxes & fees
20 Oct - 21 Oct
Wedding Villa in Chianti - Villa la Veronica

DEP. SERENELLA x2+2 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona

The price is AU$770
includes taxes & fees
16 Oct - 17 Oct
DEP. SERENELLA x2+2 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

10.0 out of 10, Exceptional, (1)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
The price is AU$2,753
includes taxes & fees
7 Oct - 8 Oct
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
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

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Chianti Region Villas information

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Frequently asked questions

How much do villas in Chianti Region cost?
Prices for villas in Chianti Region range between and 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 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.

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