
Radda in Chianti Rentals
- 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 $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 $595 per night (USD)
Expedia
Casa Lucomeni, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Casa Lucomeni is a charming holiday home in the Chianti region, ideal for two families or a group of friends. It consist ...
From $595 per night (USD)Expedia
- From $338 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 $338 per night (USD)VRBO
- From $555 per night (USD)
Expedia
Il Corno, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Il Corno is a beautifully restored farmhouse in a stunning panoramic position, ideal for a large family or a group of fr ...
From $555 per night (USD)Expedia
- From $11741 per night (USD)
VRBO
Traditional Stone House in the Heart of Chianti
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for those who want to enjoy a relaxing holiday in the Chianti countryside among vineyards and woods. The place i ...
From $11741 per night (USD)VRBO
- From $3828 per night (USD)
Expedia
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)Expedia
- 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 $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 $170 per night (USD)
VRBO
An enchanting cottage for a perfect vacation
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Leccino is one of three houses that are part of Podere Pornanino, a 36-hectare organic farm producing extra virgin olive ...
From $170 per night (USD)VRBO
- From $379 per night (USD)
Expedia
Molino del Ponte, Radda in Chianti, Italy
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
If you have ever wondered what was life like in the Tuscan region of Italy in the 1600s, look no further than Molino del ...
From $379 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 $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
- Click For Pricing
VRBO
VILLA SARA Gracious vineyard home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Villa Sara is situated on a hilltop in Panzano, in the heart of the Chianti Classico premium wine region. Exterior Descr ...
Click For PricingVRBO
- 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 $315 per night (USD)
VRBO
L'Angolino In Radda in Chianti, Tuscany
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Property for exclusive use Beautiful stone farmhouse, completely independent, 120 sq. m., holding up to 6 persons with t ...
From $315 per night (USD)VRBO
- From $1066 per night (USD)
VRBO
Cosoli, Charming Two-story Historical Villa Situated In The Heart Of Chianti
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Cosoli is a family house and the main residence of the owners. It is ideally located right in the middle of Chianti Clas ...
From $1066 per night (USD)VRBO
- From $1542 per night (USD)
VRBO
Cresta del Chianti, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 9
- Bathrooms:
- 11
- Sleeps:
- 18
Cresta del Chianti is a beautifully restored stone farmhouse in a peaceful hilltop location, surrounded by well-kept gar ...
From $1542 per night (USD)VRBO
- From $168 per night (USD)
Expedia
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)Expedia
- From $775 per night (USD)
VRBO
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)VRBO
- From $203 per night (USD)
Expedia
La Terrazza by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Terrazza is a typical manor house, located in the heart of the Chianti Classico area, which preserves the atmosphere ...
From $203 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 $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
- Click For Pricing
VRBO
Ancient hamlet with swimming pool in the heart of Chianti - Il Melograno
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
<p>Situated in a rural area, this welcoming vacation home brings all of Castellina in Chianti within your reach. Jump in ...
Click For PricingVRBO
- From $932 per night (USD)
Expedia
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)Expedia
- From $602 per night (USD)
VRBO
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)VRBO
- From $343 per night (USD)
VRBO
stunning villa in Chianti, village walking distance, breathtaking view, Wi Fi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
There’s a place in Chianti where you can have the privilege of rediscovering the past. This is a place where taste, aes ...
From $343 per night (USD)VRBO
- From $531 per night (USD)
VRBO
Docciole: Chianti Villa and Pool for 12
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
Docciole is a wonderful family villa, once a Tuscan farmhouse, converted and designed for family reunions - it provides ...
From $531 per night (USD)VRBO
- From $189 per night (USD)
Expedia
Il Cipresso, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Il Cipresso is a lovingly furnished holiday home, ideal for a couple or a small family. It is located on the ground floo ...
From $189 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 PricingVRBO
- 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 $1622 per night (USD)
VRBO
Marangole 12, Emma Villas
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
The Price includes: -Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - ...
From $1622 per night (USD)VRBO
- From $131 per night (USD)
Expedia
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)Expedia
- Click For Pricing
VRBO
Appartamento per 5 nel Chianti Classico con Piscina Vicino a Siena
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
<p>Close to ecotours, birdwatching, and more, this pet-friendly apartment brings it all within reach. Jump into your car ...
Click For PricingVRBO
- Click For Pricing
Expedia
Appartamento per 4 nel Chianti Classico con Piscina Vicino a Siena
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>A short distance from ecotours, birdwatching, and more, this pet-friendly apartment lets you experience it all. Jump ...
Click For PricingExpedia
- 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 $168 per night (USD)
VRBO
The Terrace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>Located in Castellina in Chianti, this welcoming apartment lets you experience it all. You're conveniently located wi ...
From $168 per night (USD)VRBO
- From $689 per night (USD)
VRBO
Villa La Poiana 10, Emma Villas
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
The Price includes: - Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - ...
From $689 per night (USD)VRBO
- From $713 per night (USD)
VRBO
Family property in the heart of Tuscany & Chianti Hillside
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Family villa (easily sleeps 16 people) with private infinity pool in the middle of vineyards and a natural reserve. Fu ...
From $713 per night (USD)VRBO
- Click For Pricing
VRBO
\"Pettirosso\" Peace and tranquility in Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment has a large bedroom with a queen size bed and a sofa bed. It is furnished with antique Tuscan furniture, ...
Click For PricingVRBO
- 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 $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 $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 $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 $182 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 $182 per night (USD)VRBO
- From $369 per night (USD)
VRBO
Eremo Chiostro In Gaiole in Chianti, Tuscany
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $369 per night (USD)VRBO
- From $691 per night (USD)
VRBO
Villa in Volpaia with 4 bedrooms sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful farmhouse with private pool is located in a very quiet and secluded position in a panoramic position of C ...
From $691 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 $744 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 $744 per night (USD)VRBO
- From $755 per night (USD)
Expedia
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 $755 per night (USD)Expedia
- From $552 per night (USD)
VRBO
Villa in Volpaia with 6 bedrooms sleeps 11
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Pozza di Volpaia is a villa with a private swimming pool located in the fortified medieval hamlet of Volpaia, in the Chi ...
From $552 per night (USD)VRBO
- From $482 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 $482 per night (USD)VRBO
- From $238 per night (USD)
VRBO
Eremo Fattore In Gaiole in Chianti, Tuscany
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $238 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Eremo Magnolia In Gaiole in Chianti, Tuscany
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $400 per night (USD)VRBO
- From $365 per night (USD)
VRBO
Eremo Granaio In Gaiole in Chianti, Tuscany
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $365 per night (USD)VRBO
- From $738 per night (USD)
Expedia
Villa in Volpaia with 6 bedrooms sleeps 12
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
This beautiful farmhouse with private pool is located in a very quiet and secluded position in a panoramic position of C ...
From $738 per night (USD)Expedia
- From $2934 per night (USD)
VRBO
Radda in Chianti 5 bedroom luxury villa rental, heated pool, wine estate
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Perched atop the undulating hills of Radda in Chianti, Villa Pancho is a picturesque, panoramic home with views of olive ...
From $2934 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 PricingExpedia
- From $106 per night (USD)
VRBO
Taglialegna apartment in Montefiorile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Taglialegna is a spacious, comfortable and well-equipped cottage. It is ideal for a couple who wants to spend time toget ...
From $106 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 $114 per night (USD)
VRBO
Spacious cottage in the heart of Chianti with wonderful views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Vinaio is a spacious cottage located on the ground floor inside the pretty village of Montefiorile. It is ideal as a bas ...
From $114 per night (USD)VRBO
- From $218 per night (USD)
Expedia
Mantegna, Galenda, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped w ...
From $218 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Il Poggetto a Vescinino, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Il Poggetto a Vescinino is a welcoming holiday home in the heart of Chianti, ideal for a family holiday. Set on a peacef ...
From $270 per night (USD)VRBO
- From $845 per night (USD)
Expedia
Solaria di Santa Maddalena 14, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Solaria di Santa Maddalena is a charming Chianti holiday home set in a secluded hilltop location, offering sweeping view ...
From $845 per night (USD)Expedia
- From $148 per night (USD)
VRBO
Casa Allegra, 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 $148 per night (USD)VRBO
- From $407 per night (USD)
Expedia
La Casa di Radda, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming v ...
From $407 per night (USD)Expedia
- From $520 per night (USD)
VRBO
Casino di Vescine, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Casino di Vescine is a charming Chianti country house in a peaceful, private setting surrounded by olive groves and the ...
From $520 per night (USD)VRBO
- From $154 per night (USD)
Expedia
Pesci, 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 $154 per night (USD)Expedia
- From $838 per night (USD)
VRBO
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tenuta lo Spugno ist ein luxuriöses Ferienhaus im Chianti, das in Alleinlage an der Seite eines Hügels liegt und einen t ...
From $838 per night (USD)VRBO
- From $115 per night (USD)
Expedia
Bella Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $115 per night (USD)Expedia
- From $998 per night (USD)
VRBO
Vivaio, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Vivaio is a spacious holiday home in the heart of Chianti Classico, surrounded by a beautifully landscaped garden with l ...
From $998 per night (USD)VRBO
- From $155 per night (USD)
Expedia
Uva, Ceperano, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ceperano stands among vineyards of native grapes that slope up a 1 Km walk to Radda in Chianti. Crafted with local stone ...
From $155 per night (USD)Expedia
- From $217 per night (USD)
VRBO
La Vigna, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- 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 $217 per night (USD)VRBO
- From $582 per night (USD)
Expedia
Casa Ceperano, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
A traditional Tuscan farmhouse in expansive grounds and surrounded by olive groves and vineyards, Casa Ceperano has been ...
From $582 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $183 per night (USD)
Expedia
Casa Dante, San Donato in Perano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perched on vines San Donato in Perano dates back to a medieval castle. The resort is restored into six individually owne ...
From $183 per night (USD)Expedia
- From $105 per night (USD)
VRBO
Casa Barbara, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $105 per night (USD)VRBO
- From $178 per night (USD)
Expedia
La Casanova, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
This charming single-storey stone cottage clings to a south-facing hillside, offering fabulous views of the surrounding ...
From $178 per night (USD)Expedia
- From $133 per night (USD)
VRBO
Casetta con Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- 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 $133 per night (USD)VRBO
- From $314 per night (USD)
Expedia
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)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 $78 per night (USD)
Expedia
Ulivo, Ceperano, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ceperano stands among vineyards of native grapes that slope up a 1 Km walk to Radda in Chianti. Crafted with local stone ...
From $78 per night (USD)Expedia
- From $696 per night (USD)
VRBO
Calafralina, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Calafralina is a spacious Chianti holiday home, ideal for several couples or a group of friends travelling together whil ...
From $696 per night (USD)VRBO
- From $238 per night (USD)
Expedia
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)Expedia
- From $375 per night (USD)
VRBO
Poggio della Villa, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Poggio della Villa is a beautiful Chianti holiday home just two kilometres from the centre of Radda, offering everything ...
From $375 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 $189 per night (USD)
VRBO
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)VRBO
- From $172 per night (USD)
Expedia
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)Expedia
- From $146 per night (USD)
VRBO
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)VRBO
- From $762 per night (USD)
Expedia
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 $762 per night (USD)Expedia
- From $171 per night (USD)
VRBO
Le Bonatte by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Typical Tuscan stone farmhouse IT5292.850.1 and annex IT5292.850.3 50 m away, situated in the heart of Chianti Classico. ...
From $171 per night (USD)VRBO
- From $721 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 $721 per night (USD)Expedia
- From $168 per night (USD)
VRBO
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)VRBO
- From $375 per night (USD)
Expedia
Le Bonatte by Interhome
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Typical Tuscan stone farmhouse IT5292.850.1 and annex IT5292.850.3 50 m away, situated in the heart of Chianti Classico. ...
From $375 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 $128 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 $128 per night (USD)Expedia




































































































