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Castellina in Chianti Rentals

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From $139 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 $139 per night (USD)
VRBO
From $200 per night (USD)
Expedia
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 $200 per night (USD)
Expedia
From $1294 per night (USD)
VRBO
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 $1294 per night (USD)
VRBO
From $188 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 $188 per night (USD)
Expedia
From $229 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 $229 per night (USD)
VRBO
From $581 per night (USD)
Expedia
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 $581 per night (USD)
Expedia
From $487 per night (USD)
VRBO
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 $487 per night (USD)
VRBO
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VRBO
Bettini In Castellina in Chianti, Tuscany
Bedrooms:
5
Bathrooms:
6
Sleeps:
11
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use St ...
Click For Pricing
VRBO
From $316 per night (USD)
VRBO
Villa Beba 6 In Castellina in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Property for exclusive use Historical 18th Century villa on two floors, 280 sq. m. with 3 double bedrooms and 2 bathroom ...
From $316 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Casa il Cipresso, in the heart of Chianti with swimming pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Cipresso house is one of the 4 houses of Borgo Montecastelli, and is located right on the border between the provinc ...
From $211 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Casa Antico Roseto - cottage with swimming pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Antico Roseto house is a portion of the manor house that stands on the top of Borgo Montecastelli. Next to the entra ...
From $503 per night (USD)
VRBO
From $179 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 $179 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Roccia 2BR apart PRM OK in restored Farm w Pool and Spa, ground floor terrace
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
After our highly appreciated and beloved villa Casa le Pigne, (ref 607748, 100+ 5 stars reviews), we have opened since 2 ...
From $249 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Casa Belmonte In Castellina in Chianti, Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Property for exclusive use Typical farmhouse with annexe, recently restructured and complete with every luxury, with a t ...
From $444 per night (USD)
VRBO
From $1062 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 $1062 per night (USD)
VRBO
From $488 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 $488 per night (USD)
Expedia
From $549 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 $549 per night (USD)
VRBO
From $149 per night (USD)
VRBO
Forno 1BR Apartment In a Restored Farm, Pool & Spa, 1st floor, 140/190cm sofabed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
After our highly appreciated and beloved villa Casa le Pigne, (ref 607748, 100+ 5 stars reviews), we have opened since 2 ...
From $149 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Casale Sandonatino In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Property for exclusive use Casale San Donatino is an old stone house, 480 sq. m., holding up to 12 persons with 6 double ...
From $531 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Romantic 2BR/2BA Cottage on Chianti Estate between Florenz + Siena
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The small cottage "Casa Capannina" - 110 sqm on 2 floors - (4pers.) - sits slight separate from the other buildings of ...
From $229 per night (USD)
VRBO
From $249 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 $249 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Arco : 2BR apart in a restored Farm w Pool and Spa, ground floor terrace
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
After our highly appreciated and beloved villa Casa le Pigne, (ref 607748, 100+ 5 stars reviews), we have opened since 2 ...
From $192 per night (USD)
VRBO
From $850 per night (USD)
VRBO
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 $850 per night (USD)
VRBO
From $929 per night (USD)
Expedia
Beautiful private villa with WIFI, private pool, TV, patio and panoramic view, close to Siena
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Conveniently located 4 km (2 mi) from San Leonino, Italy in the tourist area "Siena And Surroundings" and only 17 km (11 ...
From $929 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Tuscany. Lovely holiday home with swimming pool.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Magnificent high-rise apartment of 80 m2. 2 large double bedrooms. Lovely bathroom w / shower, toilet and bidet. Living ...
From $248 per night (USD)
VRBO
$\BELLAVISTA\ Stunning 1BR/1BA Loft in the Chianti hills between Florence+ Siena$
From $177 per night (USD)
VRBO
\"BELLAVISTA\" Stunning 1BR/1BA Loft in the Chianti hills between Florence+ Siena
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Bellavista (2-4 persons) (approx. 55 sqm) small well equipped built-in kitchen, 1 bedroom, 1 bathroom, living-room w ...
From $177 per night (USD)
VRBO
$\LA TANA\ family-style 2BR/1BA Apt in the Chianti Hills between Florence/Siena$
From $200 per night (USD)
VRBO
\"LA TANA\" family-style 2BR/1BA Apt in the Chianti Hills between Florence/Siena
Bedrooms:
1
Bathrooms:
2
Sleeps:
1
La Tana (4 persons) - approx. 65 sqm, 2 BA, 1 BA, live-in kitchen, sitting room, front house terrace, 2 community parki ...
From $200 per night (USD)
VRBO
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VRBO
Fontani In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Characteristic and small grou ...
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VRBO
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VRBO
Visentini In Castellina in Chianti, Tuscany
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Characteristic and small grou ...
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VRBO
From $105 per night (USD)
Expedia
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 $105 per night (USD)
Expedia
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VRBO
Spazzavento In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use St ...
Click For Pricing
VRBO
From $5063 per night (USD)
Expedia
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Bedrooms:
10
Bathrooms:
9
Sleeps:
18
A truly luxury Villa among the world famous Tuscan hills. Located only a short drive from Florence and Siena, surrounded ...
From $5063 per night (USD)
Expedia
From $147 per night (USD)
VRBO
Nice apartment in villa with pool, WIFI, TV, terrace and pets allowed, close to San Gimignano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Nestled in the serene Tuscan countryside of Poggibonsi, Italy, "La Mirandola" is a beautifully renovat ...
From $147 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Nice apartment in villa with WIFI, pool, TV, terrace and pets allowed, close to San Gimignano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Nestled in the serene Tuscan countryside of Poggibonsi, Italy, "La Mirandola" is a beautifully renovat ...
From $147 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Lovely apartment in villa with pool, WIFI, TV, terrace and pets allowed, close to San Gimignano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Nestled in the serene Tuscan countryside of Poggibonsi, Italy, "La Mirandola" is a beautifully renovat ...
From $152 per night (USD)
VRBO
From $196 per night (USD)
Expedia
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 $196 per night (USD)
Expedia
From $195 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 $195 per night (USD)
VRBO
From $586 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 $586 per night (USD)
VRBO
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VRBO
Guidi In Castellina in Chianti, Tuscany
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Characteristic and small grou ...
Click For Pricing
VRBO
From $146 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 $146 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Private Villa with WIFI, private pool, A/C, 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 $401 per night (USD)
VRBO
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VRBO
Umiliati In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use Ch ...
Click For Pricing
VRBO
From $249 per night (USD)
VRBO
Fioraie villa with pool and breathtaking views for 6 people
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
<p>Situated in a rural area, this welcoming villa brings all of Castellina in Chianti within your reach. Jump into your ...
From $249 per night (USD)
VRBO
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VRBO
Carraretto In Castellina in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Characteristic and small grou ...
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VRBO
From $222 per night (USD)
VRBO
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 $222 per night (USD)
VRBO
From $1148 per night (USD)
Expedia
Villa Delle Upupe 8, Emma Villas
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Price includes: - Utilities: electricity, water, gas for cooking purposes - weekly linen, initial and final cleaning ...
From $1148 per night (USD)
Expedia
From $3154 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 $3154 per night (USD)
VRBO
From $209 per night (USD)
VRBO
Agriturismo with pool and view close to the center of Castellina in Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Godenano di Mezzo is an ancient farm located in the heart of the Castellina in Chianti countryside, in the cradle of the ...
From $209 per night (USD)
VRBO
From $832 per night (USD)
VRBO
Villa in San Leonino with 6 bedrooms sleeps 12
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
This beautiful property with private pool is part of the Campalli estate, a huge farm of 750 acres that produces Chianti ...
From $832 per night (USD)
VRBO
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VRBO
Ceccatelli In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use St ...
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VRBO
From $1002 per night (USD)
VRBO
Villa Arnica B: A graceful cottage surrounded by vineyards and olive groves, with Free WI-FI.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Villa Arnica B is a graceful cottage surrounded by vineyards and olive groves. It sleeps four people. From Villa Arnica ...
From $1002 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Nice apartment in villa with A/C, pool, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Property Summary Nestled among rolling fields and vineyards in the heart of Tuscany, Country House "Cignanbianco" is an ...
From $150 per night (USD)
Expedia
From $215 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 Nestled among rolling fields and vineyards in the heart of Tuscany, Country House "Cignanbianco" is an ...
From $215 per night (USD)
VRBO
From $102 per night (USD)
Expedia
Lovely apartment in villa with A/C, WIFI, pool, TV, patio, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Property Summary Nestled among rolling fields and vineyards in the heart of Tuscany, Country House "Cignanbianco" is an ...
From $102 per night (USD)
Expedia
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VRBO
Boschi In Castellina in Chianti, Tuscany
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Characteristic and small group of farmhouses set inside a large property which covers an area of about 460 hectares near ...
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VRBO
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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 ...
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Expedia
From $285 per night (USD)
VRBO
Venus, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $285 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Bellosguardo, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bellosguardo is a charming Chianti holiday home set on a hill, offering stunning panoramic views over vineyards and the ...
From $341 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Borea, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $285 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Capanna Leopoldina 8, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, ...
From $415 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Athena-Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $367 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Capanna Leopoldina 10, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, ...
From $520 per night (USD)
Expedia
From $683 per night (USD)
VRBO
Macia Viva, Castellina in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Macia Viva is a charming holiday home in Chianti, set in a secluded position on a hill with beautiful views over olive g ...
From $683 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Pandora, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $285 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Athena, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $206 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Casanovina, Castellina in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casanovina is a beautiful holiday villa in the Chianti region, set on an open ridge with spectacular views over the typi ...
From $436 per night (USD)
Expedia
From $136 per night (USD)
VRBO
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, ...
From $136 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, ...
From $187 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Villa Beba, Castellina in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Villa Beba is a welcoming holiday home in Chianti, peacefully located on a hillside with wide views over vineyards, oliv ...
From $511 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $184 per night (USD)
Expedia
From $435 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 $435 per night (USD)
VRBO
$Farmhouse in the Chianti \La Foresta 1\ with swimming pool$
From $178 per night (USD)
Expedia
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 $178 per night (USD)
Expedia
From $2048 per night (USD)
VRBO
Large Chianti Estate, Tuscany weddings, retreats, celebrations, workshops
Bedrooms:
15
Bathrooms:
15
Sleeps:
33
Podere Patrignone is a large estate surrounded by vines, olives and lush forest, and sits on top of a hill with 360-degr ...
From $2048 per night (USD)
VRBO
From $104 per night (USD)
Expedia
House in a typical village in the heart of Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in a pretty and peaceful village on the top of a hill in the Chianti area which overlooks a landscape of olive t ...
From $104 per night (USD)
Expedia
From $108 per night (USD)
VRBO
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 $108 per night (USD)
VRBO
From $134 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 $134 per night (USD)
Expedia
From $138 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 $138 per night (USD)
VRBO
From $134 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 $134 per night (USD)
Expedia
From $914 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 $914 per night (USD)
VRBO
From $1895 per night (USD)
Expedia
Luxury Villa in Chianti with Winery up to 10pax
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Villa Di Castellina is an elegant country house in the charming village of Castellina in Chianti in the heart of Chianti ...
From $1895 per night (USD)
Expedia
Click For Pricing
VRBO
Villa Montespertoli In Castellina in Chianti, Tuscany
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use La ...
Click For Pricing
VRBO
From $202 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 $202 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Casa Fioraie - House with private pool
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 $407 per night (USD)
VRBO
$Farmhouse in chianti with swimming pool \ Foresta 2\$
From $232 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 $232 per night (USD)
VRBO
From $315 per night (USD)
VRBO
La Misura, cottage with garden and swimming pool on the hills of Chianti
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provin ...
From $315 per night (USD)
VRBO
From $124 per night (USD)
Expedia
detached villa with private pool and garden
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
<p>Located in a rural area, this welcoming vacation home lets you experience it all in Castellina in Chianti. There's co ...
From $124 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Agriturismo with swimming pool and view near the center of Castellina in Chianti
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 $176 per night (USD)
VRBO
From $461 per night (USD)
Expedia
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 $461 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Santantimo In Castellina in Chianti, Tuscany
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use Th ...
From $496 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Stunning villa for 12 guests with WIFI, private pool, TV, terrace and pets allowed
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Property Summary Nestled among lush green trees in the tranquil Tuscan countryside of Poggibonsi, Italy, Podere Gioia i ...
From $438 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Antica Posta, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Antica Posta is one of only two carefully restored villas created from former farm buildings. Set within the beautiful l ...
From $257 per night (USD)
VRBO
From $923 per night (USD)
Expedia
Villa Tregole, Castellina in Chianti, Siena and Chianti
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
The vine-clad hills of Chianti are the classic image of Tuscany and the beautiful backdrop for Villa Tregole. Here in th ...
From $923 per night (USD)
Expedia
From $1239 per night (USD)
VRBO
Villa Arnica A: A characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves, with Free WI-FI.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Villa Arnica A is a characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves. ...
From $1239 per night (USD)
VRBO
From $223 per night (USD)
Expedia
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 $223 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Riserva di Fizzano Residence
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
<p>While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a refrigera ...
From $236 per night (USD)
VRBO
From $391 per night (USD)
Expedia
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Casa degli Ulivi is one of the 4 houses of Borgo Montecastelli, and is located right on the border between the provi ...
From $391 per night (USD)
Expedia
From $739 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 $739 per night (USD)
VRBO
From $126 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 $126 per night (USD)
Expedia
From $463 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 $463 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
<p>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 $197 per night (USD)
Expedia

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Castellina in Chianti Rentals

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Results: 190 Rentals