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Check prices for these dates

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

Villas in Chianti Region

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 SAR 1,344
SAR 2,745 total
includes taxes & fees
17 Sep - 18 Sep
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 SAR 1,029
SAR 2,596 total
includes taxes & fees
6 Sep - 7 Sep
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."
The price is SAR 1,310
SAR 1,722 total
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
Pool

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

10.0 out of 10, Exceptional, (1)
The price is SAR 11,320
SAR 13,491 total
includes taxes & fees
5 Sep - 6 Sep
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 SAR 6,651
SAR 7,614 total
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 10 guests in 5 bedrooms
Pool

Villa Cicogna Private Villa - sleeps 10 guests in 5 bedrooms

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 SAR 567
SAR 567 total
includes taxes & fees
20 Aug - 21 Aug
Villa Cicogna Private Villa - sleeps 10 guests in 5 bedrooms
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. "
The price is SAR 5,876
SAR 8,713 total
includes taxes & fees
24 Aug - 25 Aug
Beautiful Tuscan home between Florence & Siena
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is SAR 26,052
SAR 28,242 total
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. "
The price is SAR 2,066
SAR 2,075 total
includes taxes & fees
3 Sep - 4 Sep
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 SAR 7,929
SAR 7,938 total
includes taxes & fees
26 Aug - 27 Aug
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Outdoor pool

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 SAR 7,881
SAR 9,020 total
includes taxes & fees
6 Sep - 7 Sep
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Villa Gabriella Chianti Toscana
Fireplace

Villa Gabriella Chianti Toscana

The price is SAR 1,344
SAR 2,745 total
includes taxes & fees
17 Sep - 18 Sep
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 SAR 6,247
SAR 9,044 total
includes taxes & fees
4 Sep - 5 Sep
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 SAR 8,330
SAR 8,435 total
includes taxes & fees
19 Sep - 20 Sep
"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 SAR 2,232
SAR 2,570 total
includes taxes & fees
7 Sep - 8 Sep
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 SAR 5,608
SAR 6,422 total
includes taxes & fees
3 Sep - 4 Sep
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 SAR 7,152
SAR 8,327 total
includes taxes & fees
14 Sep - 15 Sep
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 SAR 6,648
SAR 7,413 total
includes taxes & fees
27 Aug - 28 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

The price is SAR 2,403
SAR 2,937 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 1,576
SAR 2,202 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 6,651 and SAR 6,651 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 594 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.