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Siena Rentals

From $84 per night (USD)
VRBO
Nice apartment in villa for 5 guests with pool, WIFI, TV, patio, pets allowed and parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Property Summary The charming country house, "Giuggiolo", is a holiday rental nestled among lush trees and vineyards in ...
From $84 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Beautiful apartment in villa for 2 guests with WIFI, pool, TV, terrace and parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property Summary Agriturismo "Bardeggiano" offers a unique vacation rental experience in Tuscany. This two-story propert ...
From $115 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $175 per night (USD)
Expedia
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 $175 per night (USD)
Expedia
From $625 per night (USD)
VRBO
Extremely panoramic villa with private swimming pool, large, well-equipped outdoor area, terrace wit
Bedrooms:
8
Bathrooms:
8
Sleeps:
18
19th C. farmhouse surrounded by woods, olive groves and vineyards. A very attractive villa deriving from the complete re ...
From $625 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Old farmhouse with the typical Tuscan architectural features. Il Poggiarone is a splendid farmhouse with typical Tuscan ...
From $459 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Cottage with private swimming pool, Jacuzzi and air conditioning. Extremely panoramic position, surr
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The holiday house Casa Cervognano, is plunged into a splendid landscape of silver olive groves and rows of vineyards, si ...
From $271 per night (USD)
VRBO
From $123 per night (USD)
Expedia
superior ground floor apartment with pool view
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Rental basis: Entire house or apartment Number of bedrooms: 1; Number of other rooms with beds: 0 Number of bathrooms: 1 ...
From $123 per night (USD)
Expedia
$Rent villa San Giovanni d\\'Asso$
From $534 per night (USD)
VRBO
Rent villa San Giovanni d\\'Asso
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
La Cavallo is a delightful two-story house right inside the little hilltown of San Giovanni d’Asso, not far from Siena. ...
From $534 per night (USD)
VRBO
$Villa to rent in San Giovanni d\\'Asso$
From $1017 per night (USD)
Expedia
Villa to rent in San Giovanni d\\'Asso
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
In the beautiful Tuscan countryside of Val d\'Orcia lays Villa San Giovanni, an ancient stone farmhouse that was complet ...
From $1017 per night (USD)
Expedia
From $336 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 $336 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Comfortable apartment with garden in an old farmhouse with swimming pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Living room with fireplace and sofa bed, dining room/kitchen, a triple bedroom (one double and one single bed or three s ...
From $163 per night (USD)
Expedia
$\Sunflower 4\ Romantic for two$
From $86 per night (USD)
VRBO
\"Sunflower 4\" Romantic for two
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
40sqm + 15sqm of private garden and patio. Private entrances on the ground floor, table for outdoor dining, bench and ro ...
From $86 per night (USD)
VRBO
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Expedia
Villa rental in Pianella near Siena - Pianella vacation villa
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
In the heart of the Chianti Classico region, this hillside estate offers a tranquil and classic Tuscan experience. Par ...
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Expedia
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VRBO
Best location Chianti Villa, private pool, beautiful garden, fully equipped
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Bascia ...
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VRBO
From $127 per night (USD)
Expedia
Small town Tuscan living at Casa Delle Campane
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Situated in the charming and historic city center of Chiusi, Casa Delle Campane is the perfect location to experience sm ...
From $127 per night (USD)
Expedia
From $601 per night (USD)
VRBO
Palazzo Pannilini-Historical residence
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Furnished apartment of about 360 square meters, located on the second floor of a noble sixteenth-century building, of hi ...
From $601 per night (USD)
VRBO
From $118 per night (USD)
Expedia
Apartment in the castle, with restaurant and swimming pool, pink
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This stunning large apartment of 80 sqm for 5 people is located in the medieval castle, near the restaurant and the rece ...
From $118 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Superb holiday home with private terrace, panoramic swimming pool and wi-fi wi-fi
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This apartment is located in a beautiful Tuscan farmhouse called "Podere Scopeto", recently renovated and consists of 9 ...
From $166 per night (USD)
VRBO
From $109 per night (USD)
Expedia
Villa Mocarello - the Holm Oak -
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This romantic apartment is located on the second floor of a 19th century Leopoldinian Villa. The independent entrance ca ...
From $109 per night (USD)
Expedia
From $193 per night (USD)
VRBO
The House of Alice, charm and relaxation
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once in Montalcino, turn around a roundabout depicting the God of Bacchus and head for Castelnuovo dell'Abate. We arrive ...
From $193 per night (USD)
VRBO
From $176 per night (USD)
Expedia
villa Mocarello - l'Ulivo -
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This romantic apartment is located on the second floor of a 19th century Leopoldinian Villa. The independent entrance ca ...
From $176 per night (USD)
Expedia
From $131 per night (USD)
VRBO
Wisdom Apartment - Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Small apartment in the historic center of Siena, near the Piazza del Campo is located in the pedestrian area is easily a ...
From $131 per night (USD)
VRBO
From $154 per night (USD)
Expedia
Casa Laura in the countryside of San Gimignano
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Casa Laura is a nice and comfortable apartment located in a residencial hamlet with free parking and shared pool. The ap ...
From $154 per night (USD)
Expedia
From $120 per night (USD)
VRBO
Casale between Siena and the Chianti hills
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Casale La Querce, a typical building of Tuscany, was built at the end of the eighteenth century by the peasants of princ ...
From $120 per night (USD)
VRBO
From $110 per night (USD)
Expedia
The Pomegranate - San Quirico d'Orcia
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This property, located in the upper part of San Quirico d Orcia, consists of two apartments: the owners live on the uppe ...
From $110 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Independent house in the historic center
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Detached house 105 sqm, townhouse,, ground floor: living room, kitchen, bathroom; floor 1: 2 bedrooms, 1 wardrobe, 1 bat ...
From $168 per night (USD)
VRBO
From $128 per night (USD)
VRBO
Farmhouse IL PODERUCCIO with views of the Val d'Orcia, for FAMILIES
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The Poderuccio offers a rich variety of accommodation for a total of eight beds, to meet all kinds of needs. Our accommo ...
From $128 per night (USD)
VRBO
From $142 per night (USD)
VRBO
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 $142 per night (USD)
VRBO
From $210 per night (USD)
Expedia
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 $210 per night (USD)
Expedia
From $102 per night (USD)
VRBO
Villa Mocarello - The Cypress -
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The apartment, located on the second floor of a Nineteenth-century Leopoldinian Villa, is reached walking through the lu ...
From $102 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Beautiful studio located in a park with private garden, swimming pool, parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The small house, called 'La Limonaia' is located within a beautiful park of a holiday home in the historic center of Sin ...
From $171 per night (USD)
Expedia
From $741 per night (USD)
VRBO
Crognole 6, Emma Villas
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Price includes: - Utilities: electricity, water, gas for kitchen use - weekly linen, initial and final cleaning - Z ...
From $741 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Casa Elia 6, Emma Villas
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Price includes: -Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - ...
From $322 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Medieval Tower unusual and atypical accomodation for your holiday
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located on top of a hill staying will give you a stunning view of the Tuscany hillsides from all angles. You can even se ...
From $461 per night (USD)
VRBO
From $604 per night (USD)
Expedia
La Casa dell'Artista 6, Emma Villas
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Price includes: - Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - ...
From $604 per night (USD)
Expedia
From $151 per night (USD)
VRBO
YOUR EXCLUSIVE HOLIDAY BETWEEN VINEYARDS AND CASTLES
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Casa Maria is a wonderful, semi detached, split level villa situated in the Villa A Sesta hamlet. Positioned in the hear ...
From $151 per night (USD)
VRBO
From $1093 per night (USD)
Expedia
Wonderful private villa for 10 people with A/C, WIFI, private pool, TV, panoramic view and parking
Bedrooms:
5
Bathrooms:
6
Sleeps:
1
Conveniently located 12 km (7 mi) from Montalcino, Italy in the tourist area "Grosseto - Maremma" and only 48 km (30 mi) ...
From $1093 per night (USD)
Expedia
From $110 per night (USD)
VRBO
Double bedroom with private bathroom, private access, garden and swimming pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Large double bedroom (18 sqm) with private bathroom, elegantly furnished with period furniture. The room can be accessed ...
From $110 per night (USD)
VRBO
From $88 per night (USD)
VRBO
Apartment in Chianciano Terme with panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The apartment is located on the ground floor in Chianciano Terme, a step away from the main Piazza Italia and the respec ...
From $88 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Large apartment with garden in an old farmhouse with swimming pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Living/dining room with fireplace and kitchenette, one double bedroom, one twin bedroom, two bathrooms with shower, full ...
From $180 per night (USD)
VRBO
From $272 per night (USD)
Expedia
CHARMING FARMHOUSE BETWEEN VALLEYS AND THE MAGIC SENESE HILLS
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Ancient Casale of 800 of 160 square meters. on a hillock at 450 m. which dominates two sides, between Siena, Volterra an ...
From $272 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Apartment in Farmhouse-House with character
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The beautiful 13th-century stone farmhouse is set on a knoll just 2km from the picturesque medieval hilltown of Cetona ( ...
From $136 per night (USD)
VRBO
From $168 per night (USD)
Expedia
House with private terrace and exceptional view Crete Senesi
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The apartment is in a Propriétée on the scenic road that leads to the Abbey of Monte Oliveto Maggiore, it is only 2km fr ...
From $168 per night (USD)
Expedia
From $242 per night (USD)
VRBO
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 $242 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Il Poggetto a Vescinino, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Tucked away behind trees, yet opening out onto breathtaking hillside views, this charming country villa is an escapist’s ...
From $267 per night (USD)
Expedia
From $807 per night (USD)
VRBO
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 $807 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Lavanda, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
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 $253 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Podere Osteria, Pienza, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Podere Osteria is a spacious holiday home in the picturesque Val d’Orcia, a UNESCO World Heritage landscape. This farmho ...
From $390 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Villa Mimosa , 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 $134 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Rosmarino, 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 $239 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Sestuccina, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sestuccina is a stylish holiday home in the heart of Chianti Classico, ideal for a couple seeking a romantic retreat, bu ...
From $334 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Peperoncino, 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 $213 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Casa del Vignaiolo, 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 $152 per night (USD)
Expedia
From $403 per night (USD)
VRBO
La Casa di Radda, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
A sleek and charming bungalow in the town of Radda in Chianti, La Casa di Radda is a lovely getaway for 5 people. It’s a ...
From $403 per night (USD)
VRBO
From $271 per night (USD)
Expedia
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 $271 per night (USD)
Expedia
From $1164 per night (USD)
VRBO
Borratella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Borratella is a spacious Chianti holiday home, ideal for a large family or a group of friends. This house offers total p ...
From $1164 per night (USD)
VRBO
From $301 per night (USD)
Expedia
La Fontanella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
La Fontanella is a traditional stone farmhouse located on the edge of the charming village of San Sano. Surrounded by vi ...
From $301 per night (USD)
Expedia
From $193 per night (USD)
VRBO
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 $193 per night (USD)
VRBO
From $757 per night (USD)
Expedia
Treccianino 12, Sovicille, Siena and Chianti
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Treccanino 12 is an elegant and spacious holiday home in Tuscany, perfectly suited for a luxurious getaway with family o ...
From $757 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Bellosguardo, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bellosguardo is a charming Chianti holiday home set on a hill, offering stunning panoramic views over vineyards and the ...
From $362 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Casetta Kiwi is a charming Chianti holiday home in the historic hamlet of Bricciano, made up of 18th-century buildings a ...
From $289 per night (USD)
Expedia
From $321 per night (USD)
VRBO
La Capannina, Colle di Val d'Elsa, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
La Capannina is a charming Chianti holiday home, perfect for a family of four or two couples looking for a peaceful stay ...
From $321 per night (USD)
VRBO
From $735 per night (USD)
Expedia
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Canonica di Vertine is a unique holiday home located in the picturesque medieval hamlet of Vertine. This historic buildi ...
From $735 per night (USD)
Expedia
From $271 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 $271 per night (USD)
VRBO
From $233 per night (USD)
Expedia
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 $233 per night (USD)
Expedia
From $495 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 $495 per night (USD)
VRBO
From $189 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 $189 per night (USD)
Expedia
From $159 per night (USD)
Expedia
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 $159 per night (USD)
Expedia
From $395 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 $395 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Capanna di Camporata is a charming Chianti holiday home, ideal for a relaxing getaway for two. This single-storey stone ...
From $186 per night (USD)
VRBO
From $461 per night (USD)
Expedia
San Gimignano Town Garden - 8 pax
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
San Gimignano Town Garden is a one in a million apartment characterized by a central location and wide internal spaces, ...
From $461 per night (USD)
Expedia
From $146 per night (USD)
VRBO
San Gimignano Apartments Vernaccia free Netflix
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Romantic nest in the heart of San Gimignano ideal for couples. The apartment has an entrance hall with living-dining roo ...
From $146 per night (USD)
VRBO
From $285 per night (USD)
Expedia
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 $285 per night (USD)
Expedia
From $353 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 $353 per night (USD)
VRBO
From $152 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 $152 per night (USD)
Expedia
From $496 per night (USD)
VRBO
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 $496 per night (USD)
VRBO
From $829 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 $829 per night (USD)
Expedia
From $167 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 $167 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Vecchio Frantoio is a beautifully restored holiday home in Chianti with a terraced garden and a large pool. Once a histo ...
From $526 per night (USD)
Expedia
From $631 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 $631 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Trifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Trifoglio is a beautifully restored stone cottage set in an authentic 18th-century hamlet in the heart of Chianti Classi ...
From $249 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Il Trebbio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Il Trebbio is a charming holiday home in Chianti, peacefully located on a hill with panoramic views over vineyards and t ...
From $445 per night (USD)
VRBO
From $135 per night (USD)
Expedia
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 $135 per night (USD)
Expedia
From $203 per night (USD)
VRBO
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 $203 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Margherita, Palazzo a Merse, Sovicille, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once part of a watermill system that Siena relied on for its flour, Palazzo a Merse sits conveniently 1 Km from the Sien ...
From $157 per night (USD)
Expedia
From $261 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 $261 per night (USD)
VRBO
From $239 per night (USD)
Expedia
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 $239 per night (USD)
Expedia
From $177 per night (USD)
VRBO
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 $177 per night (USD)
VRBO
From $293 per night (USD)
Expedia
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 $293 per night (USD)
Expedia
From $474 per night (USD)
VRBO
Macia Viva, Castellina in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Macia Viva is a charming holiday home in Chianti, set in a secluded position on a hill with beautiful views over olive g ...
From $474 per night (USD)
VRBO
From $602 per night (USD)
Expedia
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 $602 per night (USD)
Expedia
From $239 per night (USD)
VRBO
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 $239 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Limonaia, Palazzo a Merse, Sovicille, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Once part of a watermill system that Siena relied on for its flour, Palazzo a Merse sits conveniently 1 Km from the Sien ...
From $115 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Torretta Barbischio is a characterful Chianti holiday home, ideal for a relaxing stay with family or friends. The buildi ...
From $526 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Private villa in heart of the Chianti, pool and wifi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Aia di Ama is a traditional Chianti country house offering the perfect setting for a relaxing holiday with friends or fa ...
From $267 per night (USD)
Expedia
From $181 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 $181 per night (USD)
VRBO
From $166 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 $166 per night (USD)
Expedia
From $295 per night (USD)
VRBO
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
L’Agrifoglio is a charming holiday home in the heart of the Chianti Classico region, set within a peaceful historic haml ...
From $295 per night (USD)
VRBO
From $262 per night (USD)
Expedia
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 $262 per night (USD)
Expedia

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