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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Villas in Chianti Region

Villa con Piscina, Sauna, Jacuzzi
Exterior

Villa con Piscina, Sauna, Jacuzzi

10.0 out of 10, Exceptional, (1)
"Beautiful property, highly recommended. "
The price is AED 1,192
AED 2,570 total
includes taxes & fees
2 Nov - 3 Nov
Villa con Piscina, Sauna, Jacuzzi
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Exterior

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

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 AED 5,381
AED 6,164 total
includes taxes & fees
3 Nov - 4 Nov
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Exterior

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 AED 7,533
AED 8,622 total
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
Outdoor pool

Villino Tre Pini with private pool in Florence by TuscanyWeGo

The price is AED 670
AED 2,573 total
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
Pool

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

The price is AED 1,050
AED 1,059 total
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
Pool

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 AED 6,614
AED 6,623 total
includes taxes & fees
5 Oct - 6 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is AED 25,612
AED 27,764 total
includes taxes & fees
5 Oct - 6 Oct
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Beautiful Tuscan home between Florence & Siena
Outdoor pool

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 AED 4,521
AED 7,129 total
includes taxes & fees
12 Oct - 13 Oct
Beautiful Tuscan home between Florence & Siena
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Property grounds

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

10.0 out of 10, Exceptional, (1)
The price is AED 6,719
AED 9,099 total
includes taxes & fees
5 Oct - 6 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
Pool

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

The price is AED 7,349
AED 8,504 total
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
Terrace/patio

"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 AED 3,591
AED 3,694 total
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~
Terrace/patio

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 AED 1,288
AED 1,688 total
includes taxes & fees
5 Oct - 6 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Terrace/patio

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

The price is AED 1,984
AED 2,509 total
includes taxes & fees
6 Oct - 7 Oct
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Pool

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 AED 4,829
AED 7,579 total
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Villa Il Signorino
Exterior

Villa Il Signorino

10.0 out of 10, Exceptional, (2)
"Nice place 👌 "
The price is AED 1,356
AED 1,916 total
includes taxes & fees
5 Oct - 6 Oct
Villa Il Signorino
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Outdoor pool

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 AED 2,789
AED 5,577 total
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
Property grounds

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

The price is AED 1,456
AED 1,456 total
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
Pool

Wedding Villa in Chianti - Villa la Veronica

The price is AED 7,232
AED 8,260 total
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
Pool

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

The price is AED 1,456
AED 1,865 total
includes taxes & fees
5 Oct - 6 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
Outdoor dining

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 AED 5,598
AED 6,666 total
includes taxes & fees
6 Oct - 7 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

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

10/10 Excellent
"Excellent breakfast. "
Karen 3-night trip
Posted 3 days ago
Palazzo Leopoldo Dimora Storica & Spa

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between and per night. These escapes offer the privacy of your own space at a price that doesn't break the bank. These prices were 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 choose from. Enter your destination and dates and lock in your perfect trip today.
Why book your villa in Chianti Region with Expedia?
We think arranging a vacation should be a breeze, so if you're looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.

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