Search Villas in Castellina in Chianti

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Villas in Castellina in Chianti

Our top choices for Castellina in Chianti villas

panoramica casa con piscina privata

7.0 out of 10, Good, (9)
"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 SAR 355
SAR 657 total
includes taxes & fees
8 Sep - 9 Sep
panoramica casa con piscina privata

Wine Apartments Florence Lawrence

The price is SAR 270
SAR 1,301 total
includes taxes & fees
31 Aug - 1 Sep
Wine Apartments Florence Lawrence

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!"
Villa Cicogna Private Villa - sleeps 10 guests in 5 bedrooms

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 SAR 7,806
SAR 8,918 total
includes taxes & fees
7 Sep - 8 Sep
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Casa dei Renai by Rentbeat

The price is SAR 233
SAR 1,104 total
includes taxes & fees
31 Aug - 1 Sep
Casa dei Renai by Rentbeat

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 SAR 41,701
SAR 41,701 total
includes taxes & fees
7 Sep - 8 Sep
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Villa con Piscina, Sauna, Jacuzzi

10.0 out of 10, Exceptional, (1)
"Beautiful property, highly recommended. "
The price is SAR 1,346
SAR 2,749 total
includes taxes & fees
17 Sep - 18 Sep
Villa con Piscina, Sauna, Jacuzzi

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

10.0 out of 10, Exceptional, (1)
The price is SAR 9,069
SAR 11,493 total
includes taxes & fees
5 Sep - 6 Sep
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

9.8 out of 10, Exceptional, (21)
"We enjoyed our stay immensely. Gabrielle was a great host. The property is great, the views are magnificent and the location allowed us to use our rental car to travel all throughout Tuscany and return in the evening. You wake up every morning with San Gimignano on a distant hill. As an added treat, there are several little towns and villages within a 2-5 kilometers that few are aware of that are also historic and picturesque. Donato, Barbarino to name a couple. Tavarnelle is a great town to...
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

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 7,892
SAR 9,032 total
includes taxes & fees
6 Sep - 7 Sep
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is SAR 26,063
SAR 28,253 total
includes taxes & fees
31 Aug - 1 Sep
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

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 1,311
SAR 1,696 total
includes taxes & fees
7 Sep - 8 Sep
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

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 7,806
SAR 8,840 total
includes taxes & fees
31 Aug - 1 Sep
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

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

The price is SAR 1,040
SAR 1,048 total
includes taxes & fees
31 Aug - 1 Sep
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 SAR 7,933
SAR 7,941 total
includes taxes & fees
2 Sep - 3 Sep
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

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 SAR 6,483
SAR 9,554 total
includes taxes & fees
11 Sep - 12 Sep
Beautiful Villa, in Florence, shared pool, 12 guests, wifi, parking

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 6,250
SAR 9,048 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

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 6,064
SAR 6,169 total
includes taxes & fees
10 Sep - 11 Sep
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

Luxury Villa Aria Firenze - 7 minutes from Duomo

10.0 out of 10, Exceptional, (2)
"The modern house is beautiful and provided all the amenities we look for in our vacation rentals. Location was great, for all our excursions. "
Luxury Villa Aria Firenze - 7 minutes from Duomo

With you from start to finish: Villa with concierge service and heated pool

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 5,287
SAR 6,058 total
includes taxes & fees
8 Sep - 9 Sep
With you from start to finish: Villa with concierge service and heated pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Castellina in Chianti Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between SAR 7,806 and SAR 7,806 per night. These stays 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 Castellina in Chianti?
You can choose from 2143 villas in Castellina in Chianti. No matter if you're traveling with the family or planning a getaway with your buddies, Expedia will help you find the ideal base for your squad.
Why book your villa in Castellina in Chianti with Expedia?
Reserving a villa in Castellina in Chianti is as simple as deciding on your travel dates and picking the option suited to your needs. In search of something affordable or luxurious, or a property that also has a kitchen and laundry? Use Expedia's search filters to narrow your results and find the perfect pad.