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

Filter

Popular Areas

From $725 per night (USD)
VRBO
Fattoria nel Chianti In Castelnuovo Berardenga, Tuscany
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Property for exclusive use Classic manor, 350 sq. m., in a panoramic location with a large garden and private swimming p ...
From $725 per night (USD)
VRBO
$Private Villa with private pool, A\/C, WIFI, TV, patio, panoramic view, close to Greve In Chianti$
From $406 per night (USD)
Expedia
Private Villa with private pool, A\/C, WIFI, TV, patio, panoramic view, close to Greve In Chianti
Bedrooms:
3
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 $406 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Welcome to our hide-away in the heart of the Chianti hills in Tuscany. If you are looking for a quiet place to stay whi ...
From $599 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Large apartment in Eco-resort in rural Chianti with amazing sunset views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A sunken terrace gives this apartment its name, with terracotta pots and garden furniture for your own use. Here you ent ...
From $237 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Umiliati In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Property for exclusive use Characteristic and small farmhouse inside a large property which covers an area of about 460 ...
From $334 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Fioraie villa with pool and breathtaking views for 6 people
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
<p>Located in a rural area, this welcoming villa lets you experience it all in Castellina in Chianti. Jump into your car ...
From $316 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Frantoio - Il Casale di Villore, Poggibonsi, Siena, Tuscany
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
It is a part of the complex of Villore. It is located beyond the country road that crosses our property. Frantoio's two ...
From $262 per night (USD)
VRBO
From $957 per night (USD)
Expedia
IL LOFT nel Chianti a 10 minuti da Siena
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nice 75 sqm flat with vaulted ceiling and independent entrance, located 80 meters from the train station, 2 km from the ...
From $957 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Carraretto In Castellina in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Characteristic and small group of farmhouses made up of 2 units set inside a large property which covers an area of abou ...
From $218 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Chianti villa, with private swimming pool! 5 rooms, 4 bathrooms
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Our Chianti Farmhouse is a portion of a large farmhouse a typical example of traditional old Tuscan peasant houses that ...
From $572 per night (USD)
Expedia
From $137 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 $137 per night (USD)
VRBO
From $1201 per night (USD)
Expedia
Villa Delle Upupe 8, Emma Villas
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
The Price includes: - Utilities: electricity, water, gas for cooking purposes - weekly linen, initial and final cleaning ...
From $1201 per night (USD)
Expedia
From $2322 per night (USD)
VRBO
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Bedrooms:
12
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 $2322 per night (USD)
VRBO
From $162 per night (USD)
VRBO
Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View
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 $162 per night (USD)
VRBO
From $433 per night (USD)
VRBO
Fiorita In Radda in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Property for exclusive use Typical country house in stone, 150 sq. m., with 4 double bedrooms and 3 bathrooms, holding u ...
From $433 per night (USD)
VRBO
From $733 per night (USD)
VRBO
Vistabella In Castelnuovo Berardenga, Tuscany
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Property for exclusive use Beautiful villa situated in the heart of the Chianti Classico region in a hilly position amon ...
From $733 per night (USD)
VRBO
From $957 per night (USD)
VRBO
Villa in Lucarelli with 6 bedrooms sleeps 10
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
This exquisitely restored farmhouse is situated in one of the most beautiful positions, right in the heart of Chianti ...
From $957 per night (USD)
VRBO
From $1187 per night (USD)
Expedia
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 $1187 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Ceccatelli In Castellina in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Property for exclusive use Stone-built farmhouse (150 m2) situated inside a large property which covers an area of about ...
From $222 per night (USD)
VRBO
From $677 per night (USD)
VRBO
Villa Arnica B: A graceful cottage surrounded by vineyards and olive groves, with Free WI-FI.
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Villa Arnica B is a graceful cottage surrounded by vineyards and olive groves. It sleeps four people. From Villa Arnica ...
From $677 per night (USD)
VRBO
From $1083 per night (USD)
VRBO
Villa Cherubina: A splendid sixteenth-century three-story villa located on top of a small hill, with Free WI-FI.
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Villa Cherubina is a splendid sixteenth-century three-story villa located on top of a small hill. It sleeps 14 people. F ...
From $1083 per night (USD)
VRBO
From $702 per night (USD)
VRBO
Villa Staggia In Poggibonsi, Tuscany
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Property for exclusive use Ancient 18th century Tuscany villa (500 m2) in a dominant position on a Chianti hill, surroun ...
From $702 per night (USD)
VRBO
$Apartment \La Magione\ in the Chianti Region$
From $100 per night (USD)
VRBO
Apartment \"La Magione\" in the Chianti Region
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The apartment is part of an old farm house located in a small village situated in the beautiful hills of the Chianti reg ...
From $100 per night (USD)
VRBO
From $143 per night (USD)
Expedia
Beautiful apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Property Summary Fattoria Petraglia is a charming rustic farmhouse dating back to the 15th century, offering six comfort ...
From $143 per night (USD)
Expedia
From $110 per night (USD)
VRBO
Nice apartment in villa for 3 guests with pool, WIFI, TV, patio, pets allowed and parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Property Summary Fattoria Petraglia is a charming rustic farmhouse dating back to the 15th century, offering six comfort ...
From $110 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Nice apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Property Summary Fattoria Petraglia is a charming rustic farmhouse dating back to the 15th century, offering six comfort ...
From $134 per night (USD)
Expedia
From $150 per night (USD)
VRBO
Cosy apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary Fattoria Petraglia is a charming rustic farmhouse dating back to the 15th century, offering six comfort ...
From $150 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Cosy apartment in villa for 5 people with pool, WIFI, TV, patio, pets allowed and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Property Summary Fattoria Petraglia is a charming rustic farmhouse dating back to the 15th century, offering six comfort ...
From $145 per night (USD)
Expedia
$Cosy apartment in villa with WIFI, A\/C, pool, TV, patio, pets allowed, panoramic view, parking$
From $140 per night (USD)
VRBO
Cosy apartment in villa with WIFI, A\/C, pool, TV, patio, pets allowed, panoramic view, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Property Summary Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castelli ...
From $140 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
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 $184 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Lovely apartment in villa with WIFI, private pool, TV, patio, pets allowed, panoramic view, parking
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Property Summary: The Reggine vinyard is a renovated 18th-century property that offers a cozy vacation rental surrounded ...
From $334 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Lovely apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
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 $173 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Property Summary: The Reggine vinyard is a renovated 18th-century property that offers a cozy vacation rental surrounded ...
From $218 per night (USD)
VRBO
$Cosy apartment in villa with WIFI, A\/C, pool, TV, patio, pets allowed, panoramic view and parking$
From $162 per night (USD)
Expedia
Cosy apartment in villa with WIFI, A\/C, pool, TV, patio, pets allowed, panoramic view and parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Property Summary Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castelli ...
From $162 per night (USD)
Expedia
$Cosy apartment in villa with A\/C, WIFI, pool, TV, patio, pets allowed, panoramic view and parking$
From $95 per night (USD)
VRBO
Cosy apartment in villa with A\/C, WIFI, pool, TV, patio, pets allowed, panoramic view and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Property Summary Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castelli ...
From $95 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Lovely apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
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 $184 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Cosy apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
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 $181 per night (USD)
VRBO
$Villa Capannuccia \/ Locanda La Capannuccia$
Click For Pricing
Expedia
Villa Capannuccia \/ Locanda La Capannuccia
Bedrooms:
5
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
Expedia
From $177 per night (USD)
VRBO
Morellino - Il Casale di Villore, Poggibonsi, Siena, Tuscany
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A private external staircase leads to this cozy apartment, ideal for two guests. The country kitchen with its antique ma ...
From $177 per night (USD)
VRBO
From $144 per night (USD)
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 ...
From $144 per night (USD)
VRBO
From $304 per night (USD)
VRBO
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 $304 per night (USD)
VRBO
From $286 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 $286 per night (USD)
VRBO
From $813 per night (USD)
VRBO
Tipical Tuscan Villa in the hearth of the Chianti
Bedrooms:
7
Bathrooms:
7
Sleeps:
13
Tuscan villa vacation rental for 13 persons Podere Felceto is a spacious, traditional, stone Tuscan villa originally bu ...
From $813 per night (USD)
VRBO
From $124 per night (USD)
Expedia
Farmhouse in old mill nestled in the beautiful Chianti hills
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The farmhouse is part of the property called Molino Bianco, an old stone mill documented since the eleventh century. As ...
From $124 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Prugnolo - Il Casale di Villore, Poggibonsi, Siena, Tuscany
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Apartment Prugnolo encompasses the entire ground floor of the main structure and furnished with a mix of antique and mod ...
From $239 per night (USD)
VRBO
From $80 per night (USD)
VRBO
Le Macine - farmhouse with pool in Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The millstones is an apartment for 2 people located in the forest farm, completely independent and separate from the oth ...
From $80 per night (USD)
VRBO
From $257 per night (USD)
VRBO
Amazing views in peaceful country setting close to many attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Il Caminetto is a lovely, bright and airy first-floor apartment. It is furnished beautifully, with a good-sized kitchen- ...
From $257 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Peacefull organic Agriturismo in the middle of Chianti Classico Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Fienile (80 mq) can host 5 - The entrance opens into a kitchen/living room with TV - The kitchen is complete with s ...
From $274 per night (USD)
VRBO
From $253 per night (USD)
VRBO
Large apartment in Eco-resort in rural Chianti with amazing sunset views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
La Terrazza ( is a lovely 2-bedroom, 2-bathroom apartment on the ground floor at Podere Patrignone. It sleeps 4-6 people ...
From $253 per night (USD)
VRBO
From $676 per night (USD)
Expedia
I Sodi di Bibbiano, Spa and private swimming pool
Bedrooms:
8
Bathrooms:
9
Sleeps:
18
Very large villa in the middle of the vineyard of the Bibbiano Chianti Classico estate. This unit has nine double bedroo ...
From $676 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Bibbiano - La Limonaia detatched lovely villa with private swimming pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This detatched villa has 2 double bedrooms and 2 bathrooms, a large living area and kitchen. The use of the swimming poo ...
From $285 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Bibbiano - Il Pero typical apartment in a wine estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Apartment Il Pero it is a 2 bedroom flat with 2 bathrooms in the same building of the show room and operations of Bi ...
From $201 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Bibbiano - Il Fico typical apartment in a wine estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Apartment Il Fico it is a 2 bedroom flat with 2 bathrooms in the same building of the show room and operations of Bi ...
From $189 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Casale Cipressi Castellina in Chianti
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
This is a great option for multi-generational families or friends who want to be spoiled. The beautifully kept Casale Ci ...
From $590 per night (USD)
VRBO
From $738 per night (USD)
VRBO
Solaria di Santa Maddalena 14, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Graced with views of hills cloaked in vineyards and olive groves, this generous-sized villa is a well located as well as ...
From $738 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Casale Cipressi, Castellina in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
This is a great option for multi-generational families or friends who want to be spoilt. The beautifully kept Casale Cip ...
From $736 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Venus, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $245 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Bellosguardo, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fancy immersing yourself in Chianti Classico country? Then look no further than Bellosguardo, the ideal choice for a fam ...
From $328 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Borea, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $245 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Casino di Vescine, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Looking for a truly spacious and well-located villa? Look no further, because this old stone house offers more than enou ...
From $482 per night (USD)
Expedia
From $133 per night (USD)
VRBO
Boscaiolo, Borgo Bonorli, Poggibonsi, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Borgo Bonorli is a hamlet of 8 houses that are nestled in a peaceful location surrounded by the Chianti hills. There are ...
From $133 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Capanna Leopoldina 8, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $360 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Athena-Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $320 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Capanna Leopoldina 10, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $452 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Antico Cipresso, Navico, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sitting hillside between Castellina in Chianti 9 Km and Panzano in Chianti 7 Km, Navico is an impossibly pretty collecti ...
From $247 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Macia Viva, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set above a valley in the heart of Chianti, Macia Viva’s views make this private, stone-built villa very special. The ma ...
From $538 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Ginestra, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Set in the foothills of Chianti, this delightful villa for two people has near-360° views of undulating Tuscan countrysi ...
From $339 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Solaria di Santa Maddalena 10, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Graced with views of hills cloaked in vineyards and olive groves, this generous-sized villa is a well located as well as ...
From $416 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Pandora, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $245 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Athena, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $171 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Casanovina, Castellina in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Set on an open ridge, to the rear of an old farm house this well-appointed villa scores top marks for its dreamy private ...
From $385 per night (USD)
VRBO
Click For Pricing
Expedia
Casale la Canonica, Castellina in Chianti, Siena and Chianti
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Formerly a priest’s house, Casale la Canonica clusters behind the church that greets you at the top of the drive. Set in ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Il Poggetto, Greve in Chianti, Florence and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This smart, stone-built villa sits proud atop a hill, offering captivating views of the rolling Chianti countryside. Arr ...
Click For Pricing
VRBO
From $117 per night (USD)
Expedia
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $117 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $161 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Casetta Erika, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
What could be quainter than a little pink cottage in a wood, surrounded by vineyards and olive groves? Casetta Erika is ...
From $326 per night (USD)
Expedia
From $585 per night (USD)
VRBO
Calafralina, Radda in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Calafralina is a wonderful stone villa set in the heart of Chianti. Comprising a main house and a cluster of cottages, i ...
From $585 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Villa Beba, Castellina in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
If you've got a larger group of family or friends that you'd like to share the best of Tuscany with - and you dream of e ...
From $468 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $151 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Detached house with private pool 30 kms from Florence, 45 from Siena, 5 village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The house lies in the centre of Tuscany, ideally positioned to visit all the most beautiful cities of this region. All a ...
From $293 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Authentic Tuscan House with an outdoor swimming pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stone-made house surrounded by green and peaceful meadow, ideal for those who like outdoor activities but suitable for t ...
From $268 per night (USD)
VRBO
$Farmhouse in the Chianti \La Foresta 1\ with swimming pool$
From $116 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 $116 per night (USD)
Expedia
$Private Villa with A\/C, WIFI, private pool, TV, patio, pets allowed, panoramic view, parking$
From $983 per night (USD)
VRBO
Private Villa with A\/C, WIFI, private pool, TV, patio, pets allowed, panoramic view, parking
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Property Summary Casale il Poggino is a charming vacation rental located in the heart of the Chianti Classico, perched o ...
From $983 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
La Tinaia is a lovely 1-bedroom apartment here at Podere Patrignone in Tuscany at the south-side of the Podere Patrignon ...
From $173 per night (USD)
Expedia
From $1553 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 $1553 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Amazing views in peaceful country setting close to many attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Il Caminetto is a lovely, bright and airy first-floor apartment. It is furnished beautifully, with a good-sized kitchen- ...
From $236 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Beautiful apartment in Chianti on organic farm with pool and 360° sunset views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
A covered entrance leads to a very light spacious kitchen/dining/sitting area with a large arched window. The ceilings a ...
From $237 per night (USD)
VRBO
$Villa \San Bartolomeo\ with Pool and Wi-Fi - Pets allowed$
From $381 per night (USD)
Expedia
Villa \"San Bartolomeo\" with Pool and Wi-Fi - Pets allowed
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Villa San Bartolomeo is located in Castellina in Chianti, 20 km from Siena, and boasts beautiful views of the hills. The ...
From $381 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Castellare Petroso, Radda in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Castellare Petroso sits on the Etruscan settlement site beneath the ancient hamlet of Colle Petroso. The villa is a reco ...
From $530 per night (USD)
VRBO
From $81 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 $81 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Tipologia Quadrilocale by Interhome
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The farm surrounded by olive groves and vineyards of Chianti. Each of 12 apartments are located in the main house and a ...
From $257 per night (USD)
VRBO
From $97 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 $97 per night (USD)
Expedia
From $141 per night (USD)
VRBO
Tipologia Bilo by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The farm surrounded by olive groves and vineyards of Chianti. Each of 12 apartments are located in the main house and a ...
From $141 per night (USD)
VRBO
From $127 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 $127 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Tipologia Trilo by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The farm surrounded by olive groves and vineyards of Chianti. Each of 12 apartments are located in the main house and a ...
From $183 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Le Buche by Interhome
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Chianti Classico 14 km from Castellina in Chianti: Dated back to the 1600, is surrounded by the magnificent Tuscan lands ...
From $256 per night (USD)
Expedia
From $125 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 $125 per night (USD)
VRBO
From $120 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 $120 per night (USD)
Expedia
From $2078 per night (USD)
VRBO
Villa la Corte By MMega
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
External Description Villa la Corte is located near Greve in Chianti, in the splendid Chianti countryside. Surrounded b ...
From $2078 per night (USD)
VRBO
From $873 per night (USD)
Expedia
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 $873 per night (USD)
Expedia

Search Your Destination Now!

Castellina in Chianti Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 371 Rentals