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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Villas in Chianti Region and around

Our top choices for Chianti Region villas

Villa con Piscina, Sauna, Jacuzzi
TV, fireplace

Villa con Piscina, Sauna, Jacuzzi

10.0 out of 10, Exceptional, (1)
"Beautiful property, highly recommended. "
The price is €627
includes taxes & fees
17 Sept - 18 Sept
Villa con Piscina, Sauna, Jacuzzi
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Interior

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 €610
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~
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."
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Pool

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

10.0 out of 10, Exceptional, (1)
The price is €3,081
includes taxes & fees
5 Sept - 6 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
Outdoor pool

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 €1,789
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
Pool

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 €130
includes taxes & fees
20 Aug - 21 Aug
Villa Cicogna Private Villa, sleeps 2 -10 guests
Beautiful Tuscan home between Florence & Siena
Outdoor dining

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. "
Beautiful Tuscan home between Florence & Siena
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is €6,450
includes taxes & fees
20 Aug - 21 Aug
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Pool

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. "
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Fridge, microwave, oven, stovetop

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 €1,813
includes taxes & fees
1 Sept - 2 Sept
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa Gabriella Chianti Toscana
Fireplace

Villa Gabriella Chianti Toscana

Villa Gabriella Chianti Toscana
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 €2,066
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
TV, fireplace

"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 €814
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
Pool

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

The price is €587
includes taxes & fees
7 Sept - 8 Sept
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
Outdoor dining

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 €1,509
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
Pool

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

The price is €1,902
includes taxes & fees
14 Sept - 15 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
Pool

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

The price is €1,693
includes taxes & fees
25 Aug - 26 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Exterior detail

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

Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Villa Il Signorino
Interior

Villa Il Signorino

10.0 out of 10, Exceptional, (2)
"Nice place 👌 "
The price is €517
includes taxes & fees
1 Sept - 2 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

Borgo Del Cabreo

Borgo Del Cabreo

10/10 Excellent
"Everything about our stay was incredible!!! My husband and I stayed here for 2 nights last week. It was a very short drive to downtown Greve and easy access to so many vineyards. I cannot wait to stay here again! We were unexpectedly upgraded to the villa upon check in which was so spacious, clean and gorgeous. It was the nicest room we have ever stayed in! The grounds of the hotel were impecable and well maintained. Every staff member we encountered went out of their way to make us feel welcome and well taken care of. We loved lounging by the pool area during our stay and the gorgeous views of the Tuscan hillsides. The breakfast on site was delicious with so many options. We especially loved the unlimited espresso and waters during our stay! We had dinner at the sister property up the street and it was outstanding. We will definitely be back! "
Kristin 2-night trip
Posted 1 day ago
Borgo Del Cabreo

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between €1,789 and €1,789 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 540 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 holiday 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.