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

Radda in Chianti Rentals

From $3828 per night (USD)
VRBO
Beautiful private villa for 12 guests with WIFI, A/C, private pool, close to Greve In Chianti
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Conveniently located 2 km (1 mi) from Radda In Chianti, Italy in the tourist area "Siena And Surroundings" and only 22 k ...
From $3828 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
---------- IMPORTANT: WE HAVE RECENTLY ADDED THIS PROPERTY TO OUR WALLET. LOOK AT OUR FEEDBACKS FOR THE OTHER PROPERTIES ...
From $410 per night (USD)
Expedia
From $255 per night (USD)
VRBO
APARTMENT IN THE HEART OF CHIANTI; BOOK DIRECTLY TO THE OWNER
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The apartment, with the classic structure of local houses with exposed beams, is independent and located on the ground f ...
From $255 per night (USD)
VRBO
From $635 per night (USD)
Expedia
Private Villa with hot tub, private pool, WIFI, TV, patio, panoramic view, close to Greve In Chianti
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Vacation rental Camporempoli is a nice stone building (400 sq m) that includes WiFi internet and private pool. The prop ...
From $635 per night (USD)
Expedia
From $932 per night (USD)
VRBO
Private Villa with private pool, WIFI, TV, terrace, panoramic view, close to Greve In Chianti
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Casavecchia is a beautiful stone building (284 sq m) with private pool and WiFi internet. The property can sleep up to ...
From $932 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Private Villa with WIFI, private pool, TV, terrace, panoramic view, close to Greve In Chianti
Bedrooms:
5
Bathrooms:
6
Sleeps:
11
Holiday home Pozza Di Volpaia is a nice stone building (300 sq m) that includes WiFi internet and private pool. The pro ...
From $602 per night (USD)
Expedia
Click For Pricing
VRBO
Villa Casa al Sole Large Private Pool, WiFi
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Overview Villa Casa al Sole is located in Florence, Tuscany. This detached vacation rental property offers Free Wi ...
Click For Pricing
VRBO
From $234 per night (USD)
Expedia
Stunning villa for 6 guests with WIFI, TV, terrace, pets allowed and panoramic view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Property Summary La Terrazza is a charming manor house in the heart of Chianti Classico region, offering an authentic ex ...
From $234 per night (USD)
Expedia
From $131 per night (USD)
VRBO
In the heart of Chianti: view over the valley, relaxation & art, wine & sun
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Val delle Corti is a small winery in Radda in Chianti. The ‘Capanna’, an old, tastefully restored natural stone hay bar ...
From $131 per night (USD)
VRBO
From $3958 per night (USD)
Expedia
Private Villa with private pool, sauna, A/C, WIFI, hot tub, TV, patio, close to Greve In Chianti
Bedrooms:
7
Bathrooms:
5
Sleeps:
11
Villa Castiglioni is a lovely holiday home with air conditioning, WiFi internet and private pool. The property can sle ...
From $3958 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Il Boschetto, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Il Boschetto is a charming Chianti holiday home with beautiful views over olive groves, vineyards and the rolling Tuscan ...
From $314 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $189 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Wonderful private villa with private pool, WIFI, A/C, TV, patio, pets allowed and panoramic view
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Property Summary Villa del Poggio is a rustic single-family house located in the peaceful countryside just 2 km from the ...
From $357 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Escape to Vineyards, Elba
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2-bedroom farmhouse situated in Radda in Chianti is suitable for a small group or family. Resting in Tuscany, Italy ...
From $171 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Pretty farmhouse with terrace
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
Situated in Radda In Chianti, Tuscany, Italy, this 2-bedroom farmhouse is ideal for families and groups with pets. Ideal ...
From $173 per night (USD)
VRBO
$Cottage \Podere in Volpaia\ with Garden & Wi-Fi$
From $270 per night (USD)
Expedia
Cottage \"Podere in Volpaia\" with Garden & Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located in Radda in Chianti, the cottage "Podere in Volpaia" has everything you need for a comfortable holiday. The 85 m ...
From $270 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The traditional holiday apartment 'Rifugio sulla via di Volpaia' is located in Radda in Chianti and is the ideal accommo ...
From $256 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Home 'Serena, Radda In Chianti' with Private Pool, Private Terrace and Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in Radda in Chianti, the holiday home Casa Serena, Radda In Chianti has everything you need for a relaxing holid ...
From $270 per night (USD)
Expedia
From $1027 per night (USD)
VRBO
Stunning private villa with private pool, WIFI, TV and patio, close to Greve In Chianti
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Villa Poggio La Croce is a beautiful stone building (400 sq m) with private pool and WiFi internet. The property can ac ...
From $1027 per night (USD)
VRBO
From $415 per night (USD)
Expedia
La Pesa di Mezzo, Radda in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
La Pesa di Mezzo is a beautifully restored Tuscan barn set in the heart of the unspoilt Chianti countryside.The property ...
From $415 per night (USD)
Expedia
From $691 per night (USD)
VRBO
Villa Pozzo della volpe
Bedrooms:
5
Bathrooms:
6
Sleeps:
11
Nestled in the heart of the picturesque Greve in Chianti, this family-friendly villa offers a tranquil oasis for your ne ...
From $691 per night (USD)
VRBO
From $2629 per night (USD)
VRBO
Luxury Villa in Radda Chianti,heatable Pool,Aircon,SPA room,gym room,sleep 10
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
This charming wine estate with panoramic views is located on the hills at just 1.5 km from Radda in Chianti, a lovely me ...
From $2629 per night (USD)
VRBO
From $453 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 $453 per night (USD)
VRBO
From $1761 per night (USD)
VRBO
Luxury Historic Villa San Piero, Panoramic Views, Romantic Chapel, Wine Cellar
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
SAN PIERO: A private, luxury Villa embedded in Chianti vineyards with panoramic views, saltwater pool and a Chapel from ...
From $1761 per night (USD)
VRBO
From $1480 per night (USD)
VRBO
Casale il Gualdo In Radda in Chianti, Tuscany
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Property for exclusive use Casale il Gualdo is an old stone house, completely independent, measuring 300 sq. m. and capa ...
From $1480 per night (USD)
VRBO
From $1521 per night (USD)
Expedia
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to this marvelous typical Tuscan stonehouse in picturesque Radda in Chianti. With 4 cozy bedrooms including 1 que ...
From $1521 per night (USD)
Expedia
From $5354 per night (USD)
VRBO
Chianti villa rental
Bedrooms:
6
Bathrooms:
5
Sleeps:
11
Summary: Villa Castiglioni is a stunning Chianti villa rental. It is situated in the Chianti region in Tuscany, an area ...
From $5354 per night (USD)
VRBO
From $1501 per night (USD)
Expedia
Villa Tower House Fattoria di Montemaggio
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Radda in Chianti, this 3-bedroom, 3-bathroom villa lets you experience it all. Fans of nature and the outd ...
From $1501 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Holiday Home 'Beretone' with Mountain View, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Overlooking the mountain, the holiday home "Beretone" in Radda in Chianti impresses guests with its fantastic views. The ...
From $203 per night (USD)
VRBO
From $686 per night (USD)
Expedia
Beautiful private villa for 14 guests with WIFI, private pool, TV, terrace and pets allowed
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Property Summary The Le Bonatte farm offers a cozy and simple vacation rental situated in the heart of the Chianti Class ...
From $686 per night (USD)
Expedia
From $1750 per night (USD)
VRBO
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Close to ecotours, cycling, and more, this family-friendly villa brings it all within reach. With convenient covered ...
From $1750 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $136 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Farmhouse 15th century in Chianti with private garden and lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $172 per night (USD)
VRBO
From $146 per night (USD)
Expedia
Ancient house in Chianti Hills with private lake and garden
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $146 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 $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
From $156 per night (USD)
VRBO
Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $156 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Beautiful apartment in villa for 20 people with private pool, WIFI, TV, terrace and pets allowed
Bedrooms:
6
Bathrooms:
10
Sleeps:
20
Property Summary Borgo Castagnoli is a beautiful manor house surrounded by fields and vineyards in Greve In Chianti, Ita ...
From $681 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Lovely apartment in villa for 10 people with private pool, WIFI, TV, terrace and pets allowed
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Property Summary Borgo Castagnoli is a beautiful manor house surrounded by fields and vineyards in Greve In Chianti, Ita ...
From $410 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $168 per night (USD)
VRBO
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Casa Secciano is located strategically between these 3 artistic cities allowing for easy access to tourist sites, but at ...
From $168 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Residence La Pieve Panzano in Chianti with Villa Le Barone pool & tennis access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Very recently renovated, the apartment is on the first floor of a typical old Tuscan house. The apartment is ideal for a ...
From $202 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Suite Conca d'Oro Panzano in Chianti with pool access from Hotel Villa Le Barone
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A 3 bedroom apartment, with access to the hotel swimming pool and tennis court On the first floor of a renovated old ho ...
From $320 per night (USD)
VRBO
From $383 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 $383 per night (USD)
Expedia
From $1132 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 $1132 per night (USD)
VRBO
From $206 per night (USD)
Expedia
Ridaldi by Interhome
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Podere Ridaldi is located in Lamole, a small town in Chianti with a restaurant, a small grocery store and a 13th century ...
From $206 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Stunning villa for 8 guests with A/C, hot tub, private pool, WIFI, TV and patio
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Property Summary Podere Ridaldi is a charming holiday rental located in the small town of Lamole, nestled in the heart o ...
From $237 per night (USD)
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 $154 per night (USD)
VRBO
Beautiful private villa for 8 guests with WIFI, private pool, TV, terrace and panoramic view
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Property Summary Caiano is a charming and rustic vacation rental located in the heart of Tuscany, 750 meters above sea l ...
From $154 per night (USD)
VRBO
From $193 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 $193 per night (USD)
Expedia
From $259 per night (USD)
VRBO
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)
VRBO
From $129 per night (USD)
Expedia
The Porchereccia delle Bartaline
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The apartment is located within our farm just steps from Panzano. It is newly renovated and well cared for in details, c ...
From $129 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 $789 per night (USD)
Expedia
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)
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 $201 per night (USD)
Expedia
Stunning villa with pool, WIFI, TV, terrace and panoramic view, close to Greve In Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Chiara House In Galenda, Chianti, Pool And Nature is located 13 km (8 mi) from Gaiole In Chianti, Italy and only 24 km ( ...
From $201 per night (USD)
Expedia
From $894 per night (USD)
VRBO
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)
VRBO
From $208 per night (USD)
Expedia
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)
Expedia
From $282 per night (USD)
VRBO
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)
VRBO
From $279 per night (USD)
Expedia
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)
Expedia
From $143 per night (USD)
VRBO
Apartment 'Cipressaia Botticelli' with Shared Pool, Private Terrace and Wi-Fi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The holiday apartment Agriturismo Cipressaia Botticelli in Greve in Chianti is the perfect accommodation for a stress-fr ...
From $143 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Apartment 'Cipressaia Bellavista' with Shared Pool, Shared Garden and Wi-Fi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The holiday apartment Agriturismo Cipressaia Bellavista is located in Greve in Chianti and is perfect for an unforgettab ...
From $142 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Apartment 'Il Magnifico' with Shared Pool, Private Terrace and Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Greve in Chianti, the holiday apartment Agriturismo Cipressaia Il Magnifico has everything you need for a com ...
From $225 per night (USD)
VRBO
From $519 per night (USD)
VRBO
Historic farmhouse in San Donato in Perano, Gaiole in Chianti, with shared pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Historic farmhouse dating back to the year 1000, between Gaiole in Chianti and Radda in Chianti with shared swimming poo ...
From $519 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 $619 per night (USD)
VRBO
Casa al Monte In Greve in Chianti - Tuscany
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Property for exclusive use Property at exclusive use. Tuscan farmhouse (400 sq. m.) with private swimming pool and Jacuz ...
From $619 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 6 persons with 2 bedrooms - Farmhouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
ED Refnr. 2899840 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are part ...
From $245 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 $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 $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 $184 per night (USD)
VRBO
In the Sienese Chianti house in an ancient village with swimming pool and tennis court
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
The apartment of about 90 square meters is located in a beautiful ancient village with swimming pool and tennis court. P ...
From $184 per night (USD)
VRBO
From $775 per night (USD)
Expedia
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
CLOSE TO 6 UNESCO WORLD HERITAGE SITES - Siena, San Gimignano, Val d'Orcia &Pienza, Florence and Pisa, inside the first ...
From $775 per night (USD)
Expedia
From $734 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 $734 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 $289 per night (USD)
VRBO
Pastore, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $289 per night (USD)
VRBO
From $2482 per night (USD)
Expedia
Borgo Merlo - Nine Bedroom Villa, Sleeps 22
Bedrooms:
9
Bathrooms:
9
Sleeps:
22
You will find Borgo Merlo in the verdant Chianti hills in the heart of Tuscany. The accommodation here comprises three n ...
From $2482 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 $492 per night (USD)
Expedia
Beautiful villa for 12 people with WIFI, private pool, TV, balcony, pets allowed and panoramic ...
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Property Summary Il Poggio is a beautiful farmhouse divided into three residential units, offering the option to book tw ...
From $492 per night (USD)
Expedia
From $612 per night (USD)
VRBO
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)
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 $132 per night (USD)
VRBO
Romantic Apartment In Chianti Classico, Castelnuovo Berardenga, Italy
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore the Chianti hills and vineyards from Romantic Apartment, a charming apartment for 2 in the heart of Tuscany. On ...
From $132 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Farmhouse in Chianti with Pool and Garden
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This magnificent farmhouse is located in one of the most beautiful areas of Tuscany. Chianti, famous throughout the worl ...
From $429 per night (USD)
Expedia
From $125 per night (USD)
VRBO
Casetta Maestrini, secciano loc. no. 49, Monti del Chianti, Cavriglia ( Arezzo).
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Close to ecotours, cycling, and more, this smoke-free vacation home brings it all within reach. Jump into your car an ...
From $125 per night (USD)
VRBO
From $397 per night (USD)
Expedia
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)
Expedia
From $783 per night (USD)
VRBO
PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
The Piaggione of Serravalle, at a glance, appears as a gem naturally cast on the highest ridges of the Chianti hills of ...
From $783 per night (USD)
VRBO
From $258 per night (USD)
Expedia
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)
Expedia
From $176 per night (USD)
VRBO
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)
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
Click For Pricing
VRBO
The Villa
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Casa al Monte is an ancient peasant residence located on the top of a hill, surrounded by olive and fruit trees. It is l ...
Click For Pricing
VRBO
From $148 per night (USD)
Expedia
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)
Expedia
From $1339 per night (USD)
VRBO
Casa all'Erta, villa with private pool
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Close to horse riding, this family-friendly villa brings it all within reach. With convenient onsite parking, you'll ...
From $1339 per night (USD)
VRBO
From $683 per night (USD)
Expedia
Casa Faraona, villa with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Imagine the perfect Chianti villa - a secluded house with a private pool and fabulous 180-degree views. That's just what ...
From $683 per night (USD)
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 $689 per night (USD)
Expedia
Private holiday house with pool in the heart of Tuscany
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Amoliv is the perfect choice for your stay in Tuscany. Here’s why you should choose to spend your time with us: Attracti ...
From $689 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Pergola, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $238 per night (USD)
VRBO
From $459 per night (USD)
Expedia
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)
Expedia

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