Castellina in Chianti, Tuscany Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Castellina in Chianti, Tuscany on RentalSaver.com!

Castellina in Chianti Rentals

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From $383 per night (USD)
VRBO
12km North of Siena with a stunning view pool &tennis 3ensuite bedrooms sleep 6
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful property is a part of an old 16th century farm situated on the top of one of hills West of Castellina in ...
From $383 per night (USD)
VRBO
From $1132 per night (USD)
Expedia
Detached villa with swimming pool and pizza oven for groups up to fourteen people.
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Our villa located within walking distance from Tregole in the famous wine region of Chianti Classico, has five spacious ...
From $1132 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Barn at Bagnaie is a luxury 3-bedroom Tuscan villa, which we have modernised and furnished to a high standard. The i ...
From $439 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Beautiful Tuscan farmhouse with stunning views of Chianti countryside
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The house forms part of the oldest wing of Le Bagnaie, a 300 year old farm on a secluded hilltop, which was converted in ...
From $374 per night (USD)
Expedia
From $474 per night (USD)
VRBO
Fully renovated Chianti country home, 10 min from Siena; stunning views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful 2-bedroom, 2-bathroom Tuscan country home is composed of a ground floor with a comfortable and welcoming ...
From $474 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Casa Belvedere cottage with swimming pool in the heart of Chianti
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
The Casa Belvedere is one of the 4 houses of Borgo Montecastelli, and is located right on the border between the provinc ...
From $338 per night (USD)
Expedia
From $834 per night (USD)
VRBO
Stunning private villa with private pool, WIFI, TV, patio and panoramic view, close to Siena
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
La Corte Di Campalli is located 4 km (2 mi) from San Leonino, Italy and only 17 km (11 mi) from Siena in the tourist are ...
From $834 per night (USD)
VRBO
From $155 per night (USD)
Expedia
Cosy apartment in villa with pool, WIFI, TV, terrace and pets allowed, close to San Gimignano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Accogli la Mirandola, an enchanting vacation rental that was once an old farmhouse, now renovated to of ...
From $155 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Nice apartment in villa with WIFI, pool, TV, terrace and pets allowed, close to San Gimignano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Accogli la Mirandola, an enchanting vacation rental that was once an old farmhouse, now renovated to of ...
From $159 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Beautiful apartment in villa with pool, WIFI, TV, terrace and pets allowed, close to San Gimignano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Accogli la Mirandola, an enchanting vacation rental that was once an old farmhouse, now renovated to of ...
From $168 per night (USD)
Expedia
From $218 per night (USD)
VRBO
BACCO- Authentic house with STUNNING VIEW - S. GIMIGNANO / SIENA / FIRENZE
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Authentic 15th-century house, situated in the middle of Chianti Classic, in the Sant Agnese Natural Park. Close San Gim ...
From $218 per night (USD)
VRBO
From $207 per night (USD)
VRBO
RAFFAELLO - Firenze /Siena /San Gimignano - SWIMMING POOL AND TENNIS COURT
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
AUTHENTIC 15TH CENTURY HOUSE IN CHIANTI CLASSICO / ON THE TOP OF A HILL OF OLIVE TREES, IN THE NATURE RESERVE OF SANT'AG ...
From $207 per night (USD)
VRBO
From $108 per night (USD)
VRBO
Villa with large garden in the Chianti hills
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Small villa with a large garden and private parking,inside a residence.The area was a mine until the 1950s and was organ ...
From $108 per night (USD)
VRBO
From $120 per night (USD)
Expedia
Casa Bruna - Cipresseta del Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in the Chianti hills, the apartment is immersed in the green oasis of the Bosco di Sant’Agnese Nature Reserve: a ...
From $120 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, close to Greve In Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Holiday home in a strategic position in Castellina in Chianti. Casa Fioraie is the ideal place to spend a relaxing and f ...
From $486 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Restored farmhouse in heart of chianti with swimming pool and tennis court.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Granaio is a tiny village composed of four groups of houses and a little church on top of a hill in the heart of Chianti ...
From $210 per night (USD)
Expedia
From $2775 per night (USD)
VRBO
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Bedrooms:
11
Bathrooms:
11
Sleeps:
23
Located in Castellina in Chianti in Tuscany, Italy, 'Isola Serena' is a beautiful private luxury villa on 4 acres of lan ...
From $2775 per night (USD)
VRBO
From $162 per night (USD)
Expedia
Nice apartment in villa with A/C, WIFI, pool, TV, patio, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Property Summary Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castelli ...
From $162 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Nice apartment in villa for 4 guests with pool, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary: The "Cellole" country house is a detached property offering six apartments for rent, nestled among tre ...
From $223 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Lovely apartment in villa for 4 people with pool, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary: The "Cellole" country house is a detached property offering six apartments for rent, nestled among tre ...
From $216 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Cosy apartment in villa with WIFI, A/C, pool, TV, patio, pets allowed and panoramic view
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Property Summary Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castelli ...
From $234 per night (USD)
VRBO
From $109 per night (USD)
Expedia
Beautiful apartment in villa with pool, A/C, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Property Summary Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castelli ...
From $109 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Cosy apartment in villa for 4 guests with pool, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary: The "Cellole" country house is a detached property offering six apartments for rent, nestled among tre ...
From $212 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Lovely apartment in villa for 4 people with WIFI, pool, TV, patio, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary: The "Cellole" country house is a detached property offering six apartments for rent, nestled among tre ...
From $230 per night (USD)
Expedia
Click For Pricing
VRBO
Villa Capannuccia / Locanda La Capannuccia
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Villa Capannuccia (Locanda La Capannuccia) is a construction from the 1600s. Located in the Chianti Classico area in the ...
Click For Pricing
VRBO
From $339 per night (USD)
Expedia
Podere Gioia by Interhome
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Podere Gioia consists of two independent housing units. Our offer includes three apartments, two of which are in the sam ...
From $339 per night (USD)
Expedia
$Farmhouse in the Chianti \La Foresta 1\ with swimming pool$
From $124 per night (USD)
VRBO
Farmhouse in the Chianti \"La Foresta 1\" with swimming pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Two-room apartment, renovated for 2-3 people with typical Tuscan furnishings Agriturismo La Foresta is a restored farmh ...
From $124 per night (USD)
VRBO
From $98 per night (USD)
Expedia
House in a typical village in the heart of Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Apartment located in a pretty and peaceful village on the top of a hill in the Chianti area which overlooks a landscape ...
From $98 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Capanna di Sopra by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property th ...
From $144 per night (USD)
VRBO
From $119 per night (USD)
Expedia
Capanna di Sotto by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property th ...
From $119 per night (USD)
Expedia
From $721 per night (USD)
VRBO
Casale Il Poggino by Interhome
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Casale il Poggino, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhous ...
From $721 per night (USD)
VRBO
From $122 per night (USD)
Expedia
La Tinaia by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property th ...
From $122 per night (USD)
Expedia
From $1535 per night (USD)
VRBO
Villa in Castellina w. Pool, Garden & Winery
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Villa di Castellina is a villa in the heart of the Tuscan hills, located 3 km from the center of Castellina in Chian ...
From $1535 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Farmhouse in the heart of the real chiantishire
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Farmhouse in the heart of Chiantishire at 3 kms minutes distance from the historical township of Castellina in Chianti. ...
From $168 per night (USD)
Expedia
Click For Pricing
VRBO
Villa with pool in Chianti countryside
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
A short distance from ecotours, cycling, and more, this smoke-free villa lets you experience it all. With convenient ...
Click For Pricing
VRBO
From $128 per night (USD)
Expedia
detached villa with private pool and garden
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Located in a rural area, this welcoming vacation home lets you experience it all in Castellina in Chianti. There's co ...
From $128 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Beautiful house on Chianti hilltop with exceptional views.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious (260 sq metres), very well equipped house on two floors forming part of renovated historic farm hamlet. The est ...
From $448 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Stunning villa for 12 people with WIFI, private pool, TV, terrace and pets allowed
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Property Summary Podere Gioia is a beautiful country house consisting of three independent apartments, two of which are ...
From $481 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Vacation home Olivo by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Country house "Olivo", detached, renovated in 2020. 500 m from the centre of Castellina in Chianti, 26 km from the centr ...
From $193 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Stunning private villa with A/C, private pool, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Property Summary Nestled in a secluded and quiet area, the newly renovated Country house "Olivo" is a charming and detac ...
From $259 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Beautiful apartment for 4 guests with A/C, WIFI and TV, close to Siena
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Il Nespolo Charming Apartment Fonterutoli - Siena, is a nice stone building (110 sq m) with air conditioning and WiFi i ...
From $365 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Chianti Classico Home Panoramic View, Castellina in Chianti, Italy
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
A unique opportunity for an authentic Tuscan experience, in this charming house in the heart of Castellina in Chianti. T ...
From $303 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Beautiful private villa with pool, WIFI, A/C, TV, patio and pets allowed, close to Greve In Chia...
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Villa Ida is located 4 km (3 mi) from Castellina In Chianti, Italy and only 19 km (12 mi) from Greve In Chianti in the t ...
From $323 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Cerretino Tettoia by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellina in Chianti: Cosy, rustic country house "Cerretino", surrounded by fields and vineyards. 3 houses in the resid ...
From $243 per night (USD)
Expedia
From $780 per night (USD)
VRBO
Cerretino group house 14 sleeps by Interhome
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Castellina in Chisnti: Cosy, historical country house "Cerretino group house 14 sleeps", 2 storeys, surrounded by meadow ...
From $780 per night (USD)
VRBO
From $894 per night (USD)
Expedia
Wonderful private villa for 14 people with private pool, A/C, WIFI, TV, patio and panoramic view
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Property Summary This historical country house "Cerretino + Tettoia" in Castellina In Chianti, Italy offers a cozy and s ...
From $894 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Nice apartment in villa for 4 guests with WIFI, pool, A/C, TV, patio and panoramic view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Cerretino is a cozy, rustic country house surrounded by fields and vineyards in Castellina In Chianti, ...
From $208 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Beautiful apartment in villa for 6 people with pool, A/C, WIFI, TV, patio and panoramic view
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Property Summary Cerretino is a cozy, rustic country house surrounded by fields and vineyards in Castellina In Chianti, ...
From $282 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Lovely apartment in villa for 4 guests with pool, WIFI, A/C, TV, patio and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Property Summary Cerretino is a cozy, rustic country house surrounded by fields and vineyards in Castellina In Chianti, ...
From $279 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Cignanbianco - Tramonto by Interhome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Country house "Cignanbianco", surrounded by fields and vineyards. 3 houses in the residence. 7 apartments in the residen ...
From $134 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Cellole - Cellole 1 (CTC150) by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $193 per night (USD)
VRBO
From $198 per night (USD)
Expedia
Cellole - Torretta (CTC153) by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $198 per night (USD)
Expedia
From $789 per night (USD)
VRBO
Stunning private villa for 16 people with private pool, A/C, WIFI, TV and veranda, close to Siena
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Villa Tregole is located 3 km (2 mi) from Fonterutoli, Italy and only 21 km (13 mi) from Siena in the tourist area "Sien ...
From $789 per night (USD)
VRBO
From $678 per night (USD)
VRBO
Casale Monte
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
The cottage in Castellina in Chianti has 6 bedrooms and has capacity for 12 people. The cottage is 480 m². The farmhouse ...
From $678 per night (USD)
VRBO
From $868 per night (USD)
VRBO
Wonderful villa with cottage and pool near Siena
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Nestled in Castellina in Chianti, this 6-bedroom, 2.5-bathroom villa brings it all within your reach. Fans of nature ...
From $868 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Wonderful cottage with pool near Siena
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in Castellina in Chianti, this 2-bedroom, 1-bathroom cottage lets you experience it all. Fans of nature and t ...
From $388 per night (USD)
Expedia
From $601 per night (USD)
VRBO
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Casa Le Pigne is an enchanting 2000sq ft, single-level villa situated in a peaceful and panoramic position (600m altitud ...
From $601 per night (USD)
VRBO
From $1433 per night (USD)
VRBO
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
Bedrooms:
6
Bathrooms:
6
Sleeps:
13
Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 6 BA Villa dates back to the 15th century ...
From $1433 per night (USD)
VRBO
From $496 per night (USD)
VRBO
Villa Beba In Castellina in Chianti, Tuscany
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Property for exclusive use Historical 18th Century villa with outbuilding, on two floors, 340 sq. m. with 5 double bedro ...
From $496 per night (USD)
VRBO
From $259 per night (USD)
VRBO
House with character
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Godenano di Mezzo is an ancient farm located in the heart of the Castellina in Chianti countryside, in the cradle of the ...
From $259 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Visit Florence, Siena, Chianti Classico, apartment 4/5 people
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Borgo Sicelle was originally a small farm typical of the Chianti region. It is situated on the summit which overlooks th ...
From $150 per night (USD)
VRBO
$Farmhouse in chianti with swimming pool \ Foresta 2\$
From $214 per night (USD)
VRBO
Farmhouse in chianti with swimming pool \" Foresta 2\"
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Agriturismo La Foresta is a restored farmhouse located on a hill, in the heart of the Chianti Classico region, in Tuscan ...
From $214 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Authentic Stone House with Pool & Scenic Views – Perfect for Nature Lovers
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in a peaceful meadow, this traditional stone house offers an idyllic retreat for those who love outdoor activiti ...
From $303 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Ancient villa in Chianti with swimming pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Ancient stone villa of 1500 on two floors composed of entrance, large living room, dining room, kitchen, three bedrooms ...
From $249 per night (USD)
VRBO
From $160 per night (USD)
VRBO
Cozy, Romantic and Ideal for a Couple
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Rocca property is immersed in the green Chianti hills, 480 meters above sea level, and is an authentic terrace overlo ...
From $160 per night (USD)
VRBO
From $734 per night (USD)
Expedia
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Beautiful 18th century property in the heart of the Chianti region, absolutely quiet location, equipped with a large poo ...
From $734 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Villa rental near Siena
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: This is a wonderful four bedroom villa rental near Siena. It is set within a small and perfectly kept medieval ...
From $374 per night (USD)
VRBO
From $491 per night (USD)
VRBO
Tuscan Villa with private swimming pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
The Cypresses Villa – Elegant Tuscan Retreat with Private Pool Located in Castellina in Chianti, in the heart of Tuscan ...
From $491 per night (USD)
VRBO
From $222 per night (USD)
VRBO
Belvedere 2+1 BR Luxe Apart In a Restored Tuscan Farm with Pool and Spa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A luxurious apartment in a quiet place in the middle of the forest After our highly appreciated and beloved villa Casa ...
From $222 per night (USD)
VRBO
From $114 per night (USD)
VRBO
Ancient Cottage in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ancient hut that has just been renovated and transformed into a delightful cottage located in a charming 16th century vi ...
From $114 per night (USD)
VRBO
From $196 per night (USD)
VRBO
La Torre Beautiful 1BR Love Nest In a Restored Farm. Pool, spa private terrace
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a small 2 floors house for you only, with direct access to a private and intimate Terrace After our highly apprec ...
From $196 per night (USD)
VRBO
From $1097 per night (USD)
VRBO
Podere La Valle 9BR, 16-20 Guests Retreats & Family In Restored Farm Spa & Pool
Bedrooms:
7
Bathrooms:
9
Sleeps:
27
Convenient for big families or friends groups, seminar, yoga- and personal development retreat. We do not host weddings. ...
From $1097 per night (USD)
VRBO
From $126 per night (USD)
VRBO
Chianti: farm 4 forest with swimming pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
farmhouse in the chianti with swimming pool; ok animals; sale of oil, wifi and TV nice living-dining room with fireplac ...
From $126 per night (USD)
VRBO
From $148 per night (USD)
Expedia
House with swimming pool. Medieval village in the heart of Chianti Classico
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
The apartment of about 100 square meters, is composed of: A kitchen with oven, microwave, dishwasher, washing machine. A ...
From $148 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Lovely country house in the Chianti region, for 4 persons, near Siena
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The 'Capanna delle Cozzole' is a beautiful 2-floor villa surrounded by the nature of 'Chiantishire', among olive trees, ...
From $176 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Beautiful villa for 10 guests with private pool, WIFI, A/C, TV and panoramic view
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Vacation rental In The Heart Of Chianti, Pool, Wifi, View - Lillia is a lovely property (400 sq m) that includes WiFi i ...
From $513 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Apartment Fonterutoli
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
'recently renovated apartment located in a medieval village between Siena and Castellina in Chianti Località Fonterutoli ...
From $175 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Stunning private villa with WIFI, A/C, TV and panoramic view, close to Greve In Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Property Villetta Cafaggio, Ac, Wifi, Panzano In Chianti is a lovely stone building (110 sq m) that includes WiFi inter ...
From $255 per night (USD)
Expedia
From $1747 per night (USD)
VRBO
Wonderful private villa with private pool, A/C, WIFI and terrace, close to San Gimignano
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Conveniently located 8 km (5 mi) from Castellina In Chianti, Italy in the tourist area "San Gimignano And Surroundings" ...
From $1747 per night (USD)
VRBO
From $99 per night (USD)
Expedia
Chalet in Chianti with swimming pool and tennis court
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in Castellina in Chianti, this welcoming vacation home brings it all within your reach. With convenient onsit ...
From $99 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Terrazza sul Chianti by Interhome
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Castellina in Chianti: Large, modern house "Terrazza sul Chianti", 2 storeys, renovated in 2025. 2 houses in the residen ...
From $397 per night (USD)
VRBO
From $612 per night (USD)
Expedia
Wonderful private villa with WIFI, private pool, TV and patio, close to Greve In Chianti
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Villa Pietrafitta is a beautiful stone building (200 sq m) with private pool and WiFi internet. The property can accomm ...
From $612 per night (USD)
Expedia
From $10801 per night (USD)
VRBO
Villa il Cellese in Tuscany by Fantasia Villas
Bedrooms:
10
Bathrooms:
10
Sleeps:
19
Situated in the heart of Tuscany, Villa Il Cellese is surrounded by 9 hectares of lush unadulterated land in the rolling ...
From $10801 per night (USD)
VRBO
From $678 per night (USD)
VRBO
Casale Santino
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The cottage in Castellina in Chianti has 5 bedrooms and has capacity for 10 people. The cottage is 400 m². Casale Santin ...
From $678 per night (USD)
VRBO
From $258 per night (USD)
VRBO
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
You'll find bicycles on site at this pet-friendly vacation home. Jump into your car and make short work of the 27-min ...
From $258 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You'll find bicycles on site at this pet-friendly vacation home. Jump into your car and make short work of the 27-min ...
From $176 per night (USD)
Expedia
From $120 per night (USD)
VRBO
Casa Patrizia by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellina in Chianti: Cosy, rustic terraced house "Casa Patrizia", 2 storeys, built in 1700, renovated in 1990, surroun ...
From $120 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in a rural area, this welcoming cottage lets you experience it all in Castellina in Chianti. With convenient ...
From $577 per night (USD)
Expedia
From $148 per night (USD)
VRBO
Beautiful private villa for 4 people with WIFI, A/C, TV, terrace, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Property Summary Welcome to "Casa Chiara," a modern two-story vacation rental built in 2009 and conveniently located jus ...
From $148 per night (USD)
VRBO
From $139 per night (USD)
Expedia
Wonderful private villa for 4 people with WIFI, pool, TV, terrace and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Property Summary Casa Patrizia is a cozy and rustic terraced house built in 1700 and renovated in 1990, offering a comfo ...
From $139 per night (USD)
Expedia
Click For Pricing
VRBO
vacation rental of 5 apartments in 3 farmhouses - max. 20 pers. - community pool
Bedrooms:
8
Bathrooms:
9
Sleeps:
9
https://youtu.be/_zIY8xTbw5A 5 spacious rustic apartments in 3 farm houses in very peaceful 15th century hamlet wit ...
Click For Pricing
VRBO
From $128 per night (USD)
Expedia
Casa Chiara by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Modern house "Casa Chiara", 2 storeys, built in 2009. 300 m from the centre of Castellina in Chianti, in a sunny positio ...
From $128 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Apartment in the heart of Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled in Castellina in Chianti, this 2-bedroom, 1-bathroom apartment brings it all within your reach. Fans of natur ...
From $188 per night (USD)
VRBO
Click For Pricing
Expedia
Setriolo by Arceno Rentals Club, exclusive Villa and Annex, Pool A/C Concierge
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
SETRIOLO IS NEWLY ADVERTISED. FOR THE FIRST THREE RESERVATIONS RECEIVED A WINE TASTING WILL BE OFFERED COMPLIMENTARY BY ...
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Expedia
From $321 per night (USD)
VRBO
Olimpia by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Pretty stone farmhouse. The property, made up of two connected units, is immersed in the countryside in the heart of Chi ...
From $321 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Cellole - Valluccia by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $184 per night (USD)
Expedia
From $459 per night (USD)
VRBO
Wonderful villa for 10 guests with A/C, WIFI, TV, patio and panoramic view
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Property Summary 'Terrazza sul Chianti' is a large, modern two-story house renovated in 2025, situated in Castellina In ...
From $459 per night (USD)
VRBO
From $756 per night (USD)
VRBO
Comfortable villa part of an organic winery, Castellina in Chianti.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located in a rural area, this welcoming villa lets you experience it all in Castellina in Chianti. You'll easily make ...
From $756 per night (USD)
VRBO
From $134 per night (USD)
VRBO
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Bedrooms:
1
Bathrooms:
3
Sleeps:
16
You'll find bicycles on site at this pet-friendly vacation home. Jump into your car and make short work of the 27-min ...
From $134 per night (USD)
VRBO
From $198 per night (USD)
Expedia
Riserva di Fizzano Residence
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a refrigera ...
From $198 per night (USD)
Expedia

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Castellina in Chianti Rentals

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Results: 182 Rentals