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Gaiole in Chianti Rentals

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From $325 per night (USD)
VRBO
La Fontanella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set on a slight rise, with extensive views of undulating vineyards, Fontanella has a relaxed feel inside and out. At the ...
From $325 per night (USD)
VRBO
From $218 per night (USD)
Expedia
I Cipressi, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $218 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
The secluded lavender-edged pool of Casetta Kiwi is sun-drenched all day long. At 18 meters in length, this is a serious ...
From $269 per night (USD)
VRBO
From $719 per night (USD)
Expedia
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
One for history lovers. Canonica di Vertine is an extraordinary property with a deep history, as one would expect from i ...
From $719 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Basilico, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $228 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Villa Rosabella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $185 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Vinaio, 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 $162 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This typical Chianti cottage is ideal for a couple who are looking for a romantic and peaceful hideaway, yet it is also ...
From $313 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Nicchio, Agriturismo Vinci, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Surrounded by the rolling Chianti hills covered with vineyards and olive groves, this property is wonderfully positioned ...
From $305 per night (USD)
VRBO
From $175 per night (USD)
Expedia
Bell´Aria, 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 $175 per night (USD)
Expedia
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
From $930 per night (USD)
Expedia
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
A delicate balance of rustic farmhouse style and modern comfort, Tenuta Lo Spugno is an extraordinary, and thoroughly pr ...
From $930 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Il Sole, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $176 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Vecchio Frantoio is a beautifully restored two-storey stone-built villa in the hamlet of Casanuova di Ama, surrounded by ...
From $626 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Valliole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This sprawling 17th-century villa occupies a dreamy position in the heart of rolling Chianti country with views across o ...
From $747 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Trifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wish list: a restored stone barn, deep in the heart of Chianti, surrounded by castles and quaint villages. If this chime ...
From $243 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Santa Lucia, 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 $184 per night (USD)
VRBO
From $621 per night (USD)
Expedia
Il Trebbio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If your Chianti villa wish-list includes a hill, a view, a private pool and a property oozing with atmosphere, you'll lo ...
From $621 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Il Balcone, Borgo Gaiole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Borgo Gaiole is a large hamlet with 40 villas, all overlooking the Chianti town of Gaiole. It's a short walk into the pr ...
From $169 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Sesamo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $199 per night (USD)
Expedia
From $261 per night (USD)
VRBO
La Torre Vecchia, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $261 per night (USD)
VRBO
From $186 per night (USD)
Expedia
La Chiocciola, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $186 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Casa Isabella, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $268 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Salvia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $234 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set in a tiny hamlet with an excellent local restaurant a short distance from Gaiole, one of Chianti’s most popular hill ...
From $626 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Private villa in heart of the Chianti, pool and wifi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Set in the heart of Chianti Classico, Aia di Ama provides a tranquil rural retreat amid vineyards and olive groves that ...
From $323 per night (USD)
Expedia
From $251 per night (USD)
VRBO
Vin Santo, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $251 per night (USD)
VRBO
From $162 per night (USD)
Expedia
Origano, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $162 per night (USD)
Expedia
From $246 per night (USD)
VRBO
La Torre, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $246 per night (USD)
VRBO
From $120 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 $120 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Pinturicchio, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $208 per night (USD)
VRBO
From $355 per night (USD)
Expedia
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Something of a Tardis, this renovated cottage in Bricciano, a hamlet of 18th-century farmhouses in the heart of the Chia ...
From $355 per night (USD)
Expedia
From $257 per night (USD)
VRBO
La Rana, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perfect for small groups of friends or a family of four who favour both privacy and proximity to local village life, thi ...
From $257 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Due Leoni, 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 $182 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Villa Violetto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $152 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Le Volte, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
What a delicious villa! It’s no surprise that Le Volte, set in a hamlet in the heart of Chianti’s hills, gets a very hig ...
From $626 per night (USD)
Expedia
From $235 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 $235 per night (USD)
VRBO
From $218 per night (USD)
Expedia
La Contessina, 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 $218 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Mietitore, 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 $173 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $164 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Vaniglia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $234 per night (USD)
VRBO
From $325 per night (USD)
Expedia
L'Oliveta, 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 $325 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Villa Giacinto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $221 per night (USD)
VRBO
From $424 per night (USD)
Expedia
La Capannina, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $424 per night (USD)
Expedia
From $745 per night (USD)
VRBO
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
With origins dating back to the early Middle Ages, Il Molinaccio was initially built as a defence watchtower and has sin ...
From $745 per night (USD)
VRBO
From $721 per night (USD)
Expedia
Villa San Michele, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
It’s no surprise to discover that the wealthy landowners who once ruled over much of this area chose this villa as their ...
From $721 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Taglialegna, 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 $153 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Sangiovese, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $291 per night (USD)
Expedia
From $131 per night (USD)
VRBO
Villa Fiorella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $131 per night (USD)
VRBO
From $403 per night (USD)
Expedia
Villa Riecine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
An exquisite combination of modern and rustic styles, set on a wine-producing country estate, Riecine is a thoroughly co ...
From $403 per night (USD)
Expedia
From $266 per night (USD)
VRBO
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 $266 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Sassolaia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to two of the Chianti’s most renowned and beautiful towns, and with views across the olive groves and vineyards, a ...
From $266 per night (USD)
Expedia
From $773 per night (USD)
VRBO
Sestuccia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Visit in the heat of the summer and you will be living outdoors at Sestuccia – and doing so in great style. The main vil ...
From $773 per night (USD)
VRBO
From $136 per night (USD)
Expedia
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 $136 per night (USD)
Expedia
From $173 per night (USD)
VRBO
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 $173 per night (USD)
VRBO
From $187 per night (USD)
Expedia
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 $187 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sangiovese all'Aia is a delightful villa and a fine choice if you are a family of four or a couple seeking just a little ...
From $283 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Il Boschetto, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set across the first floor of a large stone farmhouse, this villa in rural Chianti offers comfortable lodgings for six p ...
From $303 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Il Paretaio, Montevarchi, Arezzo and Cortona
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Head for the hills on the edge of the Chianti to stay at this little beauty – a romantic bolthole just for two. You’ll f ...
From $287 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Casa Maria, Villa a Sesta, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Villa a Sesta is a collection of six Chianti country cottages of traditional Tuscan stone with terracotta tiles and expo ...
From $293 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Ciacchieri, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You will feel a real part of Tuscan life in Ciacchieri, a cheerfully decorated apartment in Gaiole, a small town at the ...
From $146 per night (USD)
VRBO
From $170 per night (USD)
Expedia
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $170 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Le Cerreta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set atop a sunlit Chianti hill near the beautiful town of Gaiole, Le Cerreta is an exceptional private hideaway. It’s sh ...
From $492 per night (USD)
VRBO
From $187 per night (USD)
Expedia
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 $187 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Maggiorana, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $234 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Casa Minuccia, Villa a Sesta, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Villa a Sesta is a collection of six Chianti country cottages of traditional Tuscan stone with terracotta tiles and expo ...
From $251 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Villa Girasole , San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $295 per night (USD)
VRBO
From $427 per night (USD)
Expedia
Casa Virginia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You will love Casa Virginia’s openness: set on a gentle slope above a vineyard, with a backdrop of olive trees, pines an ...
From $427 per night (USD)
Expedia
From $203 per night (USD)
VRBO
La Taverna, 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 $203 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Podere Filazzi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Immersed in a deep green valley with rolling hills and gorgeous views, Podere Filazzi is a country villa with charming d ...
From $245 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Malvasia, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $218 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Timo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $182 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Casa Zaccardi, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $458 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Angolino, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tucked away at the end of a quiet road, yet barely a mile from Radda, one of Chianti’s main market towns, Angolino is a ...
From $299 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Bacco, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $203 per night (USD)
VRBO
From $225 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 $225 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Poggio della Villa, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Arrive at this delightful stone-built villa on the edge of the Chianti town of Radda and you will quickly shake off any ...
From $370 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Mastro 3, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $241 per night (USD)
Expedia
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VRBO
BOSSI CASTLE App. Geranium
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Castle of Bossi is located in the southern part of the Chianti Classico in the municipality of Castelnuovo Berardeng ...
Click For Pricing
VRBO
Click For Pricing
Expedia
CASTLE OF BOSSI Ginestra Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Castello di Bossi is located in the southern part of the Chianti Classico in the municipality of Castelnuovo Berarde ...
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Expedia
$Apartment \Pieve\ - Chianti as you've always dreamed of it$
From $216 per night (USD)
VRBO
Apartment \"Pieve\" - Chianti as you've always dreamed of it
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 70 m² apartment with private garden, for pleasant outdoor breakfasts or relaxing al fresco dinners on summer evening ...
From $216 per night (USD)
VRBO
From $146 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) Colombaia
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the ...
From $146 per night (USD)
VRBO
From $270 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) San Polo
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $270 per night (USD)
VRBO
From $227 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) San Giusto
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $227 per night (USD)
VRBO
From $227 per night (USD)
VRBO
BELLAVISTA (Castello di Bossi) SAN PAOLO apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $227 per night (USD)
VRBO
From $123 per night (USD)
Expedia
Antico Borgo di Montefienali - Apartment il Portico
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
From $123 per night (USD)
Expedia
Click For Pricing
VRBO
Antico Borgo Montefienali - Apartment La Chiocciola
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
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VRBO
From $221 per night (USD)
Expedia
Podere Lucignano Secondo - La Mangiatoia
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $221 per night (USD)
Expedia
From $1485 per night (USD)
VRBO
Gated Private Estate🏡 San Felice Adjacent 🌈Classic Views, 🍇Vineyards
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Private residence of an American owner, made available to guests certain periods from May through October. A gated and p ...
From $1485 per night (USD)
VRBO
From $140 per night (USD)
Expedia
La Farfalla n°5 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $140 per night (USD)
Expedia
From $999 per night (USD)
VRBO
VILLA GAIA - Five Bedroom Villa, Sleeps 10
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
A typical Chianti Villa in Tuscany, once a a 15th century mill, located in the countryside, just 15 minutes from Siena, ...
From $999 per night (USD)
VRBO
From $1493 per night (USD)
Expedia
Villa Agresto, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Agresto sits on its own private hilltop, decorated with vineyards manicured by the Ricasoli estate. With 360-degree surr ...
From $1493 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Podere Lucignano Secondo - La Villa
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $534 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Podere Lucignano Secondo - Le Logge
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $238 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
Could there be a more apt setting for a Chianti wine region villa than on the sloping vines of a famous wine estate? Mul ...
From $747 per night (USD)
VRBO
From $124 per night (USD)
Expedia
Tribolina by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Manor house "Tribolina", 550 m a.s.l.. 2 houses in the residence. 3 km from the centre of Cavriglia, 12 km from the cent ...
From $124 per night (USD)
Expedia
From $134 per night (USD)
VRBO
La Colomba n°4 by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $134 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Lo Scoiattolo n° 10 by Interhome
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $273 per night (USD)
Expedia
From $140 per night (USD)
VRBO
Il Ghiro n°8 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $140 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Special offer Newly renovated fine detached villa with fireplace.
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Independent house in an ancient village of the '900, located 10 km from the center of Siena (15 minutes by car). Just r ...
From $115 per night (USD)
Expedia

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Results: 380 Rentals