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Featured Villas in Castellina in Chianti

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (84)
"Located in one of the prettiest areas of Tuscany, this is a beautiful property. Our host and owner Alessandro was a true pleasure to deal with. Like dealing with a family member, he was attentive, kind, informative, helpful, and truly interested in making sure we were comfortable and had everything we needed. Alessandro was kind enough to set up our dinners with local cooks - who were two beautiful ladies that cooked with joy and passion, and really cared about their food - local favourites. If...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Terrace/patio
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
10.0 out of 10, Exceptional, (93)
"We had the most amazing stay at this beautiful villa. Everything about it was picturesque and relaxing. This villa has all of the modern amenities but still exudes Tuscan charm. Pre- visit communication was smooth and very prompt. The highlight of the stay was the dinner cooked for us the first night by Chef Vanna and Francesca. I am not exaggerating when I say it was by far the best meal we had during our trip to Tuscany and we ate at many very nice restaurants. If you are booking a stay I...
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Outdoor pool
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (104)
"we had an amazing week at this villa with 18 family members, age 6 months to 87 years. Jacobo and Beatrice were so nice , very welcoming and super helpful with transportation and amenities nearby. If we had any problems we could easily text and Jacopo would immediately answer . i would recommend coming here ! Faboulous"
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
Pool
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
10.0 out of 10, Exceptional, (71)
"We so enjoyed our nine nights at Leo’s beautiful place in Belforte. This is a tiny Medieval town at the top of the mountain. So quiet except for the church bells, and occasional kids running through the town. A nice retreat from the business of other Tuscany tourist attractions. The home is very spacious with four bedrooms and large outdoor gathering areas . Fruit trees and grape vines in the yard add to the ambiance . The kitchen was well equipped, with everything one would need and the...
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
Outdoor dining
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
9.4 out of 10, Exceptional, (28)
"The location of the villa is fantastic and the villa itself is extremely well laid out, clean and comfortable. We loved our stay and the host was incredibly helpful and friendly. We would be happy to stay again, our one suggestion would be that perhaps some of the finishings could be updated, they were obviously very trendy and cutting edge when designed, but perhaps could be improved by some modernisation, and I think the villa would then be perfect."
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
Outdoor pool
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
10.0 out of 10, Exceptional, (41)
"Had a great two week vacation at Eduardo's place in Reggello. Beautiful little cabin with a pool and well kept yard, set within an olive orchard and vineyard. Hosts passed along some fresh eggs from the hens and tomatoes from the property. The house seems quite new by Italian standards and is in excellent condition. Pool is fantastic. We had a great stay and would highly recommend this spot for small groups and families. "
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool
BEAUTIFUL VILLA with private Pool in the heart of Chianti
10.0 out of 10, Exceptional, (19)
"We rented the villa after a family event. The owners and their son are very charming and accommodating. We enjoyed the villa as it is very authentic. Felt like we were locals. It has separate areas almost like apartments within the villa which is great if you have many couples. One of the rooms has bunk beds and the other two twin beds. It’s important to know you can’t walk anywhere so a car is needed. That’s the only reason for my location rating. Excellent villa to spend time with friends and...
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Luxury Villa in the Florentine hills
Fridge, microwave, oven, stovetop
Luxury Villa in the Florentine hills
9.8 out of 10, Exceptional, (129)
"My husband and I stayed a month here. While access is kind of a challenge (need a car and the roads are narrow) the location is beautiful and very quiet. We decided it was a nice change from the crowds and noise of Florence and other tourist spots at the end of the day. The villa itself is exactly as portrayed in the pictures. Big, clean, well equipped for any stay. We found the best way to get into Florence was to drive into Grassina, park and take the local buses. Great access and saved a...
Luxury Villa in the Florentine hills
Villa luna with pool and garden near the center of Siena
Fridge, microwave, oven, dishwasher
Villa luna with pool and garden near the center of Siena
9.0 out of 10, Wonderful, (27)
"The home had everything we needed. The view from the villa was truly picturesque. A+++++!"
Villa luna with pool and garden near the center of Siena
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor pool
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Authentic country house originally a convent, dates back to around the year 1000
Outdoor dining
Authentic country house originally a convent, dates back to around the year 1000
9.6 out of 10, Exceptional, (50)
"Beautiful place and a very friendly and helpful host. Authentic Tuscan farmhouse with no frills. Lovely views all round, especially from the terrace. Excellent bar/ restaurant within walking distance. It was very hot when we were there, so the location of the pool across the road was a problem. Otherwise,great."
Authentic country house originally a convent, dates back to around the year 1000
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Outdoor dining
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
10.0 out of 10, Exceptional, (31)
"The villa was very nice, but the path to get to the villa is very poorly maintained. Also, during our stay the roof leaked into one of the bedrooms and the heating system was not set up for cold weather yet.."
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Your panoramic house in Tuscany between vineyards and olive groves.
Exterior
Your panoramic house in Tuscany between vineyards and olive groves.
9.8 out of 10, Exceptional, (31)
"Enrico and Simona have a special place in an incredible area. The views are amazing and all of the little towns are historic and have great little restaurants. The Villa is well equipped and very comfortable. The hosts are kind and full of helpful info on the area. Make sure to take a guided tour of the Benedictine Monastery nearby. Couldn’t have a better stay in Tuscany."
Your panoramic house in Tuscany between vineyards and olive groves.
Double room with private parking within walking distance of downtown!
Property grounds
Double room with private parking within walking distance of downtown!
7.6 out of 10, Good, (5)
"Easy Walking to all there is to see in Siena!!! Car is parked safely in front of villa no extra charge. Quiet Apartment is in the basement bathroom is upstairs. Monica is very welcoming and informative. "
The price is NZ$240
includes taxes & fees
16 Nov - 17 Nov
Double room with private parking within walking distance of downtown!
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Property grounds
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
10.0 out of 10, Exceptional, (46)
"This place exceeded all of our expectations. The host and his family were amazing and very accommodated. Perfect size for two couples. Bedrooms and bathrooms were private. The location was perfect. We were able to take daily trips everywhere in Tuscany between 15 minutes and one hour. The house and pool were even better than the pictures portray. The place came stocked with everything you need For your vacation. If ever back in Tuscany I would definitely stay here again."
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Villa with private swimming pool in quiet area, private garden, panoramic views
Outdoor pool, pool loungers
Villa with private swimming pool in quiet area, private garden, panoramic views
10.0 out of 10, Exceptional, (8)
"La maison est très calme, très propre et bien équipée, accessible en partie par un chemin de terre depuis le joli village de Radicondoli, . La vue sur les collines avoisinantes est très agréable, en particulier de la piscine (hors-sol). Il faut compter environ 45 minutes de jolies routes pour se rendre à Sienne, Volterra ou San Giminiano. Beaucoup d'animaux sauvages dans la nature, si vous êtes chanceux comme nous... Sarka est une hôtesse sympathique et attentionnée. Avec son mari, elle produit...
Villa with private swimming pool in quiet area, private garden, panoramic views
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
Interior
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
9.8 out of 10, Exceptional, (25)
"Beautiful property and old world charm. Perfectly located and lovely hosts."
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
Villa with view and private pool
Outdoor pool
Villa with view and private pool
10.0 out of 10, Exceptional, (20)
"We loved the villa and the location. We couldn’t have asked for a better view giving us a wonderful feeling of Tuscany. The closeness to Volterra, coupled with the great supermarket and lovely pizzerias made it special. Guilia was very responsive and helpful at all times. We would come back in a heartbeat. "
Villa with view and private pool
Luxury Villa with large pool close to Florence
Outdoor pool
Luxury Villa with large pool close to Florence
10.0 out of 10, Exceptional, (62)
"Beautiful, historic villa with a fantastic view of the valley below. Our hosts were friendly, helpful and entertaining as well. The icing on the cake was Fonsi's providing breakfast and cooking dinners as requested. Her chef skills were more than we could ask for. "
Luxury Villa with large pool close to Florence
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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Other property types in Castellina in Chianti

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Hu Firenze Camping In Town
Seasonal outdoor pool
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1268)
"Overall our stay in Hu Firenze was great. The restaurant on location was really cool and tasted pretty great too. The staff was friendly and helpful. Our little house was a big tent basically. Interesting but annoying when people would come check it out or tap on our house (happened a couple times). It was kinda funny but always awkward. We had a bed, closet, mini fridge, and bathroom. They had a shuttle to take you partially into town or you could walk to Firenze Rovezzano (train station)....
The price is NZ$107
includes taxes & fees
6 Nov - 7 Nov
Hu Firenze Camping In Town
PopArtment
Bicycling
PopArtment
9.0 out of 10, Wonderful, (681)
"Great place for families."
The price is NZ$185
includes taxes & fees
17 Nov - 18 Nov
PopArtment
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.

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Prices for villas in Castellina in Chianti range between NZ$240 and NZ$240 per night. Whatever your budget, you can find someplace that fits the bill on Expedia. 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?
Castellina in Chianti has 1451 villas to select from. Find a stay that’s right for you quickly and easily by checking the “Villa” box under the “Property type” tab in our handy filter tool.
What is there to do near my villa in Castellina in Chianti?
Castellina in Chianti has enough sights to keep you on the hop for weeks (or months!), starting with Buondonno Winery. Casa Vinicola Luigi Cecchi, Archaeological Museum of Chianti and City Hall Castellina In Chianti are other renowned attractions. If you have time to spare, Walls of Monteriggioni and Montecalvario are great additions to your itinerary.