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Gaiole in Chianti Rentals

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From $212 per night (USD)
VRBO
Lavanda, 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 $212 per night (USD)
VRBO
From $146 per night (USD)
Expedia
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 $146 per night (USD)
Expedia
From $303 per night (USD)
VRBO
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 $303 per night (USD)
VRBO
From $150 per night (USD)
Expedia
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 $150 per night (USD)
Expedia
Click For Pricing
VRBO
Villa 'Castello di Monteluco a Lecchi' with Hill View, Pool & Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The villa Castello di Monteluco a Lecchi in Gaiole in Chianti is the ideal accommodation for a relaxing holiday with a m ...
Click For Pricing
VRBO
From $482 per night (USD)
Expedia
Il Gufo n°1 by Interhome
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $482 per night (USD)
Expedia
From $87 per night (USD)
VRBO
Cerbiatto n°5A by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $87 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Pulcino n°3 by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $115 per night (USD)
Expedia
From $147 per night (USD)
VRBO
Il Pettirosso n°7 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $147 per night (USD)
VRBO
From $3922 per night (USD)
Expedia
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Offering panoramic vistas over Chianti’s hills and woodlands, Villa Gaiole is a serene escape in the Tuscan countryside ...
From $3922 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Coccinella n°6 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 $146 per night (USD)
VRBO
From $150 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 $150 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Pergola, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $228 per night (USD)
VRBO
From $173 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 $173 per night (USD)
Expedia
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VRBO
House Ciaccheri Holidays in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The house is located in the heart of the Chianti Classico area within the town of Gaiole in Chianti, the town square is ...
Click For Pricing
VRBO
From $142 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 $142 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Terrazza Alta, Borgo Gaiole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
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 $262 per night (USD)
VRBO
From $149 per night (USD)
Expedia
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 $149 per night (USD)
Expedia
From $180 per night (USD)
VRBO
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 $180 per night (USD)
VRBO
From $105 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 $105 per night (USD)
Expedia
From $134 per night (USD)
Expedia
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 $134 per night (USD)
Expedia
From $151 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 $151 per night (USD)
Expedia
From $115 per night (USD)
VRBO
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)
VRBO
From $171 per night (USD)
Expedia
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 $171 per night (USD)
Expedia
From $1502 per night (USD)
VRBO
Villa Biancofiore: A characteristic and welcoming three-story ancient tuscan country house situated in the heart of the Tuscan countryside, with Free WI-FI.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Villa Biancofiore is a characteristic and welcoming three-story ancient tuscan country house situated in the heart of th ...
From $1502 per night (USD)
VRBO
From $1145 per night (USD)
Expedia
Belvilla by OYO Villa Petra Sei
Bedrooms:
6
Bathrooms:
4
Sleeps:
6
This villa with a private swimming pool and tennis court is located in the heart of the Chianti Classico region in Tusca ...
From $1145 per night (USD)
Expedia
From $508 per night (USD)
VRBO
Holiday Home 'Vertine Countryside' with Private Terrace, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Located in Gaiole in Chianti, the holiday home Vertine Countryside has everything you need for a relaxing holiday. The 2 ...
From $508 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We offer you a chance for rural adventure in a wild and isolated setting unparalleled in Tuscany. You are invited to sha ...
From $433 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We offer you a chance for rural adventure in a wild and isolated setting unparalleled in Tuscany. You are invited to sha ...
From $442 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We offer you a chance for rural adventure in a wild and isolated setting unparalleled in Tuscany. You are invited to sha ...
From $379 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Campo al Sole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Campo al Sole is a perfectly private retreat for two, set in the heart of the Chianti Classico wine region. If you’re dr ...
From $224 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Casa Faraona, villa with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Imagine the perfect Chianti villa - a secluded house with a private pool and fabulous 180-degree views. That's just what ...
From $681 per night (USD)
Expedia
From $116 per night (USD)
VRBO
Holiday Home 'L'arco Della Fonte' with Private Terrace, Wi-Fi and Air Conditioning
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The holiday home L'arco della Fonte is located in Gaiole in Chianti and is the ideal accommodation for a relaxing getawa ...
From $116 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Casa Vecchia, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
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 $1115 per night (USD)
VRBO
Villa Barbischio - Gaiole In Chianti ,Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from th ...
From $1115 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Livio House, a garden with a view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Gaiole in Chianti, this welcoming apartment brings it all within your reach. Jump into your car and make s ...
From $355 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Montechioccioli by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cosy, rustic 3-family house "Montechioccioli", surrounded by vineyards. 3 apartments in the property. In the hamlet Riet ...
From $130 per night (USD)
VRBO
From $1865 per night (USD)
Expedia
Casolare di Rietine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casolare di Rietine is a beautifully furnished Chianti holiday home with sweeping views over vineyards, olive groves and ...
From $1865 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Casa dei Mandorli, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perched atop the picturesque Ama hills, Casa dei Mandorli offers a serene escape with breathtaking views that capture th ...
From $346 per night (USD)
VRBO
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Expedia
Montechioccioli by Interhome
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Cosy, rustic 3-family house "Montechioccioli", surrounded by vineyards. 3 apartments in the property. In the hamlet Riet ...
Click For Pricing
Expedia
From $142 per night (USD)
VRBO
Cozy house nestled in the nature of the Chianti Classico hills
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Gaiole in Chianti, this welcoming vacation home lets you experience it all. Jump into your car and make sh ...
From $142 per night (USD)
VRBO
From $945 per night (USD)
Expedia
Villa la Pecine by MMega
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
External Description Villa la Pecine, an ancient mill on the Pecine stream from which it takes its name, stands in a ...
From $945 per night (USD)
Expedia
From $134 per night (USD)
VRBO
Cosy apartment for 2 people with WIFI, TV and parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property Summary This charming 2-family house is situated in the heart of Gaiole In Chianti, Italy, offering an ideal v ...
From $134 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Il Fienile, 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 $308 per night (USD)
Expedia
From $126 per night (USD)
VRBO
GuestHost - Comfy Apt near the Castle of Brolio
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Gaiole in Chianti, this welcoming vacation home lets you experience it all. Jump into your car and make sh ...
From $126 per night (USD)
VRBO
From $2159 per night (USD)
Expedia
Villa Gallonero: A spacious age-old farm house surrounded by the greenery, with Free WI-FI.
Bedrooms:
12
Bathrooms:
15
Sleeps:
30
Villa Gallonero is a spacious age-old farm house surrounded by the greenery. It sleeps 30 people. From Villa Gallonero y ...
From $2159 per night (USD)
Expedia
From $1016 per night (USD)
VRBO
Vacation home for 10 guests with 300m² in Adine Di Gaiole In Chianti (273260)
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Located in Gaiole in Chianti, this welcoming vacation home lets you experience it all. Jump into your car and make sh ...
From $1016 per night (USD)
VRBO
From $1685 per night (USD)
VRBO
Villa Chianti, elegant villa in Gaiole in Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Located in a rural area, this welcoming villa lets you experience it all in Gaiole in Chianti. Jump into your car and ...
From $1685 per night (USD)
VRBO
From $790 per night (USD)
VRBO
Lo Spicchio, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Amid the rolling hills of Chianti, where the fabled Classico wines are made, stands Lo Spicchio. The stout stone house, ...
From $790 per night (USD)
VRBO
From $2730 per night (USD)
Expedia
Private and Peaceful Medieval Villa in the heart of Chianti
Bedrooms:
7
Bathrooms:
7
Sleeps:
18
Tenuta di San Giusto; a very peaceful and characteristic villa dated from the year 1000. Situated in the municipality of ...
From $2730 per night (USD)
Expedia
From $4506 per night (USD)
VRBO
Luxury Tuscany Hillside Villa With Heated Pool Close to Chianti Towns and Siena
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Perfectly positioned on a hill with 360-degree views of the verdant Chianti countryside, Le Pratola is the perfect luxur ...
From $4506 per night (USD)
VRBO
From $2418 per night (USD)
Expedia
Borgo San Polino, villa with private pool
Bedrooms:
9
Bathrooms:
9
Sleeps:
20
Located in Gaiole in Chianti, this welcoming villa brings it all within your reach. Jump into your car and make short ...
From $2418 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Casa Momi - One Bedroom Villa, Sleeps 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This romantic home in the Chianti Classico countryside offers stunning views of rolling hills, forests, and vineyards an ...
From $482 per night (USD)
VRBO
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Expedia
Hilltop Apartment for two
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in a rural area, this welcoming apartment lets you experience it all in Cavriglia. Jump into your car and mak ...
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Expedia
From $154 per night (USD)
VRBO
Cottage in Moncione near Florence, Siena & Arezzo, walk to restaurant
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
La Rota is a delightful cottage set among peaceful olive groves, barely a ten minute stroll from the village of Moncioni ...
From $154 per night (USD)
VRBO
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Expedia
CASA TOLOMEI - Giulietta
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
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
From $253 per night (USD)
VRBO
Chianti Sunshine with Pool and View
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $253 per night (USD)
VRBO
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Expedia
Villino Ersilia, the charm of Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Castelnuovo Berardenga, this welcoming vacation home brings it all within your reach. With convenient onsi ...
Click For Pricing
Expedia
From $4720 per night (USD)
VRBO
Villa Radda - 11 Guests
Bedrooms:
6
Bathrooms:
5
Sleeps:
11
VILLA RADDA - FLORENCE AREA With its beautiful medieval tower set up as a wine bar, the villa offers spectacular views a ...
From $4720 per night (USD)
VRBO
From $257 per night (USD)
Expedia
LA RONDINAIA. CHARMING HOUSE WITH GARDEN AND POOL. AMAZING VIEW
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LA RONDINAIA apartment was obtained by restoring an ancient cellar where wine was left to age in large oak vats. Beneat ...
From $257 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to the Tuscan countryside! Our stone farmhouse sits on a hillside in Chianti, just 15 km from the center of Sien ...
From $548 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Private Villa with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
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 $356 per night (USD)
Expedia
From $234 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) San Sano
Bedrooms:
1
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 $234 per night (USD)
VRBO
From $110 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 $110 per night (USD)
Expedia
From $113 per night (USD)
VRBO
Special offer Newly renovated fine detached villa with fireplace.
Bedrooms:
0
Bathrooms:
2
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 $113 per night (USD)
VRBO
From $207 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 $207 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Il Boschetto, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Il Boschetto is a charming Chianti holiday home with beautiful views over olive groves, vineyards and the rolling Tuscan ...
From $312 per night (USD)
VRBO
From $200 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 $200 per night (USD)
Expedia
From $193 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 $193 per night (USD)
VRBO
From $364 per night (USD)
Expedia
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 $364 per night (USD)
Expedia
From $308 per night (USD)
VRBO
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 $308 per night (USD)
VRBO
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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 ...
Click For Pricing
Expedia
From $234 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 $234 per night (USD)
VRBO
From $279 per night (USD)
Expedia
BELLAVISTA (Castle of Bossi) San Polo
Bedrooms:
1
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 $279 per night (USD)
Expedia
From $241 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 $241 per night (USD)
VRBO
From $183 per night (USD)
Expedia
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 $183 per night (USD)
Expedia
From $300 per night (USD)
VRBO
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 $300 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 $836 per night (USD)
VRBO
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 $836 per night (USD)
VRBO
From $194 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 $194 per night (USD)
Expedia
From $406 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 $406 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
From $268 per night (USD)
VRBO
BELLAVISTA San Piero
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $268 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Apartment 'Casale Rosennano - Loggia' with Shared Garden & Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Located in the medieval village of Rosennano, the apartment 'Casale Rosennano - Loggia' is part of a characteristic farm ...
From $142 per night (USD)
Expedia
From $115 per night (USD)
VRBO
Apartment Casale Rosennano - Scuderie with Shared Garden & Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the medieval village of Rosennano, the apartment Casale Rosennano - Scuderie is part of a characteristic farm ...
From $115 per night (USD)
VRBO
From $116 per night (USD)
Expedia
Apartment Casale Rosennano - Tinaia with Shared Garden & Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in the medieval village of Rosennano, the apartment Casale Rosennano - Tinaia is part of a characteristic farmho ...
From $116 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Apartment Casale Rosennano - Padronale with Shared Garden & Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the medieval village of Rosennano, the apartment Casale Rosennano - Padronale is part of a characteristic far ...
From $149 per night (USD)
VRBO
From $2722 per night (USD)
Expedia
Villa Le Cantine di Cerreto, a magnificent villa for rent in the Sienese countryside, with an in...
Bedrooms:
8
Bathrooms:
8
Sleeps:
14
Villa Cerreto is owned by a renowned Florentine family belonging to the fashion industry and dates back to the 1700’s. T ...
From $2722 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Casa Secciano is located strategically between these 3 artistic cities allowing for easy access to tourist sites, but at ...
From $165 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Villa Nova - Apartment with swimming pool
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
Beautiful country house situated in the heart of the renowned Chianti Classico region, approx. 20 km from Siena away. Th ...
From $184 per night (USD)
Expedia
From $257 per night (USD)
VRBO
LA TORRE, AN EAGLE NEST ABOVE THE TUSCANY LANDSCAPE
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Casa La Torre is located in an ancient palace overlooking the small hamlet of Rosennano. Its renovation was completed in ...
From $257 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Typical, Charming with Chianti View, Pool & Jacuzzi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $222 per night (USD)
Expedia
From $243 per night (USD)
VRBO
LA LOGGIA. HOUSE WITH STUNNING VIEW ABOVE THE CHIANTI REGION AND PANORAMIC POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranq ...
From $243 per night (USD)
VRBO
From $1606 per night (USD)
Expedia
Villa Siena 10, Emma Villas
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The price includes: - Utilities water - gas for kitchen use and hot water - wireless internet connection - weekly linen, ...
From $1606 per night (USD)
Expedia
From $132 per night (USD)
VRBO
In the heart of Chianti: view over the valley, relaxation & art, wine & sun
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Val delle Corti is a small winery in Radda in Chianti. The ‘Capanna’, an old, tastefully restored natural stone hay bar ...
From $132 per night (USD)
VRBO
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Expedia
Appartamento per 5 nel Chianti Classico con Piscina Vicino a Siena
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Close to ecotours, birdwatching, and more, this pet-friendly apartment brings it all within reach. Jump into your car ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Appartamento per 4 nel Chianti Classico con Piscina Vicino a Siena
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A short distance from ecotours, birdwatching, and more, this pet-friendly apartment lets you experience it all. Jump ...
Click For Pricing
VRBO
From $187 per night (USD)
VRBO
Townhouse Casa Gorizia - Authentic Tuscany
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Set in a medieval hamlet amongst the Tuscan Hills, Montebenichi feels a world away and yet is close to some of Tuscany's ...
From $187 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Traumblick in die Toskana vom Ferienhaus mit Pool auf Hügel zw. Siena u. Florenz
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Close to hiking trails, mountain biking, and more, this family-friendly vacation home brings it all within reach. Jum ...
From $417 per night (USD)
VRBO
From $3334 per night (USD)
Expedia
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 $3334 per night (USD)
Expedia

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