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Featured Villas in Castellina in Chianti

Our top choices for Castellina in Chianti villas

panoramica casa con piscina privata

7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
The price is AU$271
includes taxes & fees
22 Sept - 23 Sept
panoramica casa con piscina privata

Wine Apartments Florence Lawrence

The price is AU$571
includes taxes & fees
16 Sept - 17 Sept
Wine Apartments Florence Lawrence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

10.0 out of 10, Exceptional, (1)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
The price is AU$3,684
includes taxes & fees
14 Sept - 15 Sept
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villino Tre Pini with private pool in Florence by TuscanyWeGo

The price is AU$1,028
includes taxes & fees
1 Oct - 2 Oct
Villino Tre Pini with private pool in Florence by TuscanyWeGo

Villa Cicogna Private Villa, sleeps 2 -10 guests

10.0 out of 10, Exceptional, (7)
"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$231
includes taxes & fees
19 Sept - 20 Sept
Villa Cicogna Private Villa, sleeps 2 -10 guests

Lovely house in the heart of Chianti

Lovely house in the heart of Chianti

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

10.0 out of 10, Exceptional, (1)
"Staff went over and above for us. Food was wonderful service 5 stars"
The price is AU$16,981
includes taxes & fees
10 Sept - 11 Sept
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Casa dei Renai by Rentbeat

The price is AU$484
includes taxes & fees
11 Sept - 12 Sept
Casa dei Renai by Rentbeat

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$3,718
includes taxes & fees
8 Oct - 9 Oct
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Beautiful Villa, in Florence, shared pool, 12 guests, wifi, parking

8.0 out of 10, Very good, (3)
"We were a group of ten friends staying in Florence to celebrate a birthday. A warm welcome awaited us. The villa itself is sizable, though for a little extra we hired the cottage too. All the rooms are tastefully, ornately and traditional appointed while all the bathrooms (most are ensuite) are wonderfully modern. The grounds are extensive (you occasionally see the gardeners during the morning) affording you a privacy hard to find elsewhere in Florence. The lanai has a large table to seat all...
The price is AU$3,938
includes taxes & fees
10 Sept - 11 Sept
Beautiful Villa, in Florence, shared pool, 12 guests, wifi, parking

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$3,617
includes taxes & fees
8 Oct - 9 Oct
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Villa con Piscina, Sauna, Jacuzzi

10.0 out of 10, Exceptional, (1)
"Beautiful property, highly recommended. "
The price is AU$1,118
includes taxes & fees
21 Sept - 22 Sept
Villa con Piscina, Sauna, Jacuzzi

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is AU$11,505
includes taxes & fees
15 Sept - 16 Sept
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

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

10.0 out of 10, Exceptional, (1)
The price is AU$4,466
includes taxes & fees
1 Oct - 2 Oct
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (141)
"Lovely property, nicely appointed, would be happy to stay there again."
The price is AU$800
includes taxes & fees
30 Sept - 1 Oct
Luxury Villa in the Florentine hills

Villa with concierge service and heated pool at 20 minute from Florence center

10.0 out of 10, Exceptional, (104)
"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$2,610
includes taxes & fees
10 Sept - 11 Sept
Villa with concierge service and heated pool at 20 minute from Florence center

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$705
includes taxes & fees
15 Sept - 16 Sept
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

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$4,380
includes taxes & fees
1 Oct - 2 Oct
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

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$3,049
includes taxes & fees
8 Oct - 9 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

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

The price is AU$3,392
includes taxes & fees
14 Sept - 15 Sept
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
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 Castellina in Chianti Hotel Reviews

Find out more about Castellina in Chianti

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

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1813 Villas
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Frequently asked questions

How much do villas in Castellina in Chianti cost?
Prepare to pay between and per night for a villa in Castellina in Chianti. No matter your budget, a perfect stay is only a few clicks away 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 Castellina in Chianti?
Lock in your holiday dates and then choose from 1813 villas in Castellina in Chianti. For a family trip, a couple's getaway and everything in between, Expedia can help you find the perfect space in a few easy clicks.
What is there to do near my villa in Castellina in Chianti?
Castellina in Chianti has enough activities and experiences to keep you on the go for weeks (or months!), starting with Monteriggioni Castle. Meleto Castle, Castello di Radda Winery and Castello di Albola are other impressive attractions. If you're hanging around a while, Badia a Coltibuono and Isole e Olena Winery will add the finishing touches to your itinerary.