Siena Rentals
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $219 per night (USD)Expedia
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 $219 per night (USD)Expedia
From $136 per night (USD)VRBO
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 $136 per night (USD)VRBO
From $235 per night (USD)Expedia
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 $235 per night (USD)Expedia
From $218 per night (USD)VRBO
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 $218 per night (USD)VRBO
From $159 per night (USD)Expedia
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 $159 per night (USD)Expedia
From $177 per night (USD)VRBO
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 $177 per night (USD)VRBO
From $147 per night (USD)Expedia
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 $147 per night (USD)Expedia
From $115 per night (USD)VRBO
The Pomegranate - San Quirico d'Orcia
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This property, located in the upper part of San Quirico d Orcia, consists of two apartments: the owners live on the uppe ...
From $115 per night (USD)VRBO
From $207 per night (USD)Expedia
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 $207 per night (USD)Expedia
From $175 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 $175 per night (USD)VRBO
From $255 per night (USD)Expedia
Farmhouse in old mill nestled in the beautiful Chianti hills
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The farmhouse is part of the property called Molino Bianco, an old stone mill documented since the eleventh century. As ...
From $255 per night (USD)Expedia
From $244 per night (USD)VRBO
Prugnolo - Il Casale di Villore, Poggibonsi, Siena, Tuscany
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Apartment Prugnolo encompasses the entire ground floor of the main structure and furnished with a mix of antique and mod ...
From $244 per night (USD)VRBO
From $130 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 $130 per night (USD)VRBO
From $211 per night (USD)VRBO
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 $211 per night (USD)VRBO
From $1220 per night (USD)Expedia
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 $1220 per night (USD)Expedia
From $743 per night (USD)VRBO
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 $743 per night (USD)VRBO
From $524 per night (USD)Expedia
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 $524 per night (USD)Expedia
From $704 per night (USD)VRBO
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 $704 per night (USD)VRBO
From $162 per night (USD)Expedia
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 $162 per night (USD)Expedia
From $945 per night (USD)VRBO
Wonderful private villa for 10 people with A/C, WIFI, private pool, TV and panoramic view
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Property Lavacchio 10 is a lovely stone building (360 sq m) that includes WiFi internet, private pool and air condition ...
From $945 per night (USD)VRBO
From $109 per night (USD)Expedia
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 $109 per night (USD)Expedia
From $179 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 $179 per night (USD)VRBO
From $318 per night (USD)VRBO
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 $318 per night (USD)VRBO
From $174 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 $174 per night (USD)VRBO
From $178 per night (USD)Expedia
Mantegna, Galenda, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Galenda is a small, charming hamlet set on a ridge in the heart of the Chianti Classico, offering beautiful views over o ...
From $178 per night (USD)Expedia
From $267 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 $267 per night (USD)VRBO
From $847 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 $847 per night (USD)Expedia
From $240 per night (USD)VRBO
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 $240 per night (USD)VRBO
From $337 per night (USD)Expedia
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 $337 per night (USD)Expedia
From $148 per night (USD)VRBO
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 $148 per night (USD)VRBO
From $228 per night (USD)Expedia
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 $228 per night (USD)Expedia
From $364 per night (USD)VRBO
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 $364 per night (USD)VRBO
From $201 per night (USD)Expedia
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 $201 per night (USD)Expedia
From $137 per night (USD)VRBO
Casa del Vignaiolo, San Sano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
San Sano is a charming hamlet located within the Chianti village of the same name, set in the heart of the Chianti Class ...
From $137 per night (USD)VRBO
From $432 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 $432 per night (USD)Expedia
From $285 per night (USD)VRBO
Venus, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $285 per night (USD)VRBO
From $598 per night (USD)Expedia
Podere Terrena, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Podere Terrena is a charming holiday home located on a small agriturismo in a wonderfully peaceful hillside setting, sur ...
From $598 per night (USD)Expedia
From $783 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 $783 per night (USD)VRBO
From $307 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 $307 per night (USD)Expedia
From $196 per night (USD)VRBO
I Cipressi, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vignale is an idyllic hamlet made up of lovingly restored former farm buildings, which now house six individually owned ...
From $196 per night (USD)VRBO
From $722 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 $722 per night (USD)Expedia
From $341 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 $341 per night (USD)VRBO
From $387 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 $387 per night (USD)Expedia
From $253 per night (USD)VRBO
Capannina, Colle di Val d'Elsa, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Capannina is a charming Chianti villa, perfect for a family of four or two couples looking for a peaceful stay surrou ...
From $253 per night (USD)VRBO
From $641 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 $641 per night (USD)Expedia
From $285 per night (USD)VRBO
Borea, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $285 per night (USD)VRBO
From $221 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 $221 per night (USD)Expedia
From $525 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 $525 per night (USD)VRBO
From $210 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 $210 per night (USD)Expedia
From $415 per night (USD)VRBO
Capanna Leopoldina 8, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, ...
From $415 per night (USD)VRBO
From $186 per night (USD)Expedia
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)Expedia
From $458 per night (USD)VRBO
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 $458 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
Agriturismo Vinci is a small, idyllic hamlet in the heart of the Chianti Classico, comprising just five charming holiday ...
From $285 per night (USD)Expedia
From $367 per night (USD)VRBO
Athena-Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $367 per night (USD)VRBO
From $156 per night (USD)Expedia
Pesci, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $156 per night (USD)Expedia
From $520 per night (USD)VRBO
Capanna Leopoldina 10, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, ...
From $520 per night (USD)VRBO
From $804 per night (USD)Expedia
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tenuta lo Spugno is a luxurious holiday villa in Chianti, set in a secluded position on the side of a hill with breathta ...
From $804 per night (USD)Expedia
From $159 per night (USD)VRBO
Il Sole, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $159 per night (USD)VRBO
From $537 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 $537 per night (USD)Expedia
From $642 per night (USD)VRBO
Valliole, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Valliole is a 17th-century villa in the Chianti region with breathtaking postcard-perfect views across the vineyards of ...
From $642 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 $190 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 $190 per night (USD)VRBO
From $163 per night (USD)Expedia
Margherita, Palazzo a Merse, Sovicille, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Palazzo a Merse is a characterful Tuscan hamlet where history and rural charm come together. The estate consists of an 1 ...
From $163 per night (USD)Expedia
From $244 per night (USD)VRBO
La Torre Vecchia, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Vignale is an idyllic hamlet made up of lovingly restored former farm buildings, which now house six individually owned ...
From $244 per night (USD)VRBO
From $168 per night (USD)Expedia
La Chiocciola, Montefienali, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Montefienali is a small, atmospheric hamlet tucked into the rolling hills of Chianti, offering a peaceful retreat surrou ...
From $168 per night (USD)Expedia
From $261 per night (USD)VRBO
Casa Isabella, San Sano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
San Sano is a charming hamlet located within the Chianti village of the same name, set in the heart of the Chianti Class ...
From $261 per night (USD)VRBO
From $683 per night (USD)Expedia
Macia Viva, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Macia Viva is a charming holiday home in Chianti, set in a secluded position on a hill with beautiful views over olive g ...
From $683 per night (USD)Expedia
From $228 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 $228 per night (USD)VRBO
From $115 per night (USD)Expedia
Limonaia, Palazzo a Merse, Sovicille, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Palazzo a Merse is a characterful Tuscan hamlet where history and rural charm come together. The estate consists of an 1 ...
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 $278 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 $278 per night (USD)Expedia
From $170 per night (USD)VRBO
Vin Santo, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vignale is an idyllic hamlet made up of lovingly restored former farm buildings, which now house six individually owned ...
From $170 per night (USD)VRBO
From $153 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 $153 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 $267 per night (USD)Expedia
La Rana, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Rana is a welcoming Chianti holiday home on the edge of the pretty village of San Sano, ideal for a family of four or ...
From $267 per night (USD)Expedia
From $952 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 $952 per night (USD)VRBO
From $148 per night (USD)Expedia
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 $148 per night (USD)Expedia
Click For PricingVRBO
Le Volte, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
Le Volte is a welcoming Chianti holiday home, ideal for a relaxing stay with family or friends. Set in a small hamlet, i ...
Click For PricingVRBO
From $171 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 $171 per night (USD)Expedia
From $214 per night (USD)VRBO
La Vigna, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $214 per night (USD)VRBO
From $139 per night (USD)Expedia
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Montefienali is a small, atmospheric hamlet tucked into the rolling hills of Chianti, offering a peaceful retreat surrou ...
From $139 per night (USD)Expedia
From $228 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 $228 per night (USD)VRBO
From $319 per night (USD)Expedia
Il Fornacino, Rapolano Terme, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
I Fornacino is a lovingly restored holiday home that once housed a historic furnace. Today, it is the perfect retreat fo ...
From $319 per night (USD)Expedia
From $285 per night (USD)VRBO
Pandora, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $285 per night (USD)VRBO
From $218 per night (USD)Expedia
L'Oliveta, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $218 per night (USD)Expedia
From $811 per night (USD)VRBO
Il Casetto, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Il Casetto is a luxurious holiday home set in a peaceful countryside location, surrounded by vineyards and rolling hills ...
From $811 per night (USD)VRBO
From $206 per night (USD)Expedia
Athena, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Podere di Casalta is a charming small hamlet set on a hillside amid the rolling landscape of the Chianti Classico, betwe ...
From $206 per night (USD)Expedia
From $436 per night (USD)VRBO
Casanovina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casanovina is a beautiful holiday villa in the Chianti region, set on an open ridge with spectacular views over the typi ...
From $436 per night (USD)VRBO
From $210 per night (USD)Expedia
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 $210 per night (USD)Expedia
From $664 per night (USD)VRBO
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Il Molinaccio is a unique holiday home in the heart of Chianti, with a rich history that stretches back to the Middle Ag ...
From $664 per night (USD)VRBO
From $826 per night (USD)Expedia
Farmhouse PODERE IL POGGETTO
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
IL POGGETTO is an agricultural farmhouse located in the heart of Tuscany on a beautiful hill a few kilometers from San G ...
From $826 per night (USD)Expedia
From $148 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 $148 per night (USD)VRBO
From $375 per night (USD)Expedia
Villa Riecine, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Villa Riecine is a luxurious holiday home located on the grounds of the renowned winery of the same name. Surrounded by ...
From $375 per night (USD)Expedia
From $203 per night (USD)VRBO
Sassolaia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sassolaia is a Chianti holiday home in a dreamlike secluded location, surrounded by olive groves and vineyards with swee ...
From $203 per night (USD)VRBO
From $840 per night (USD)Expedia
Sestuccia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sestuccia is a beautifully renovated stone house set in the rolling hills of the Chianti Classico region. This modern vi ...
From $840 per night (USD)Expedia
From $102 per night (USD)VRBO
Il Sole e la Luna, Partena, Colle di Val d'Elsa, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Partena is a small, authentic hamlet set on a hill in the beautiful Val d’Elsa. It consists of just 18 houses, most of w ...
From $102 per night (USD)VRBO
From $195 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 $195 per night (USD)Expedia
From $304 per night (USD)VRBO
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sangiovese all’Aia is a charming holiday home in Chianti, located on the grounds of Agriturismo Trappoline, where wine a ...
From $304 per night (USD)VRBO
From $344 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 $344 per night (USD)Expedia