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Gaiole in Chianti Rentals

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From $401 per night (USD)
VRBO
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 $401 per night (USD)
VRBO
From $78 per night (USD)
Expedia
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 $78 per night (USD)
Expedia
From $91 per night (USD)
VRBO
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 $91 per night (USD)
VRBO
From $132 per night (USD)
Expedia
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 $132 per night (USD)
Expedia
$Private Villa with A\/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking$
From $378 per night (USD)
VRBO
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 $378 per night (USD)
VRBO
From $122 per night (USD)
Expedia
Apartment in the castle, with restaurant and swimming pool, Ginestra
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Nice and comfortable apartment for 4 persons (70sqm), in the hamlet near the castle, about 200 meters from the swimming ...
From $122 per night (USD)
Expedia
From $237 per night (USD)
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 ...
From $237 per night (USD)
VRBO
From $227 per night (USD)
Expedia
BELLAVISTA (Castle of Bossi) San Sano
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 $227 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Dionisia, Capannole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled between vine covered hills, Capannole is a peaceful hamlet of eleven private houses which date back to 1400. A f ...
From $211 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Cosy apartment in villa with WIFI, pool, TV, terrace, pets allowed, panoramic view and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $159 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Beautiful apartment in villa with WIFI, pool, TV, terrace, pets allowed, panoramic view and park...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $272 per night (USD)
VRBO
From $154 per night (USD)
Expedia
Beautiful apartment in villa with WIFI, pool, TV, terrace, pets allowed, panoramic view and park...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $154 per night (USD)
Expedia
From $462 per night (USD)
VRBO
Nice apartment in villa with WIFI, private pool, TV, terrace, pets allowed, panoramic view, parking
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $462 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Holiday house Pievasciata for 1 - 4 persons with 2 bedrooms - Holiday home
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
ED Refnr. 2025493 You will stay in a Tuscan-style farmhouse that has been preserved in its natural charm for many centu ...
From $180 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Portion Farmhouse nestled in the heart of Chianti with private pool,
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
A short distance from ecotours, mountain biking, and more, this family-friendly vacation home lets you experience it ...
From $223 per night (USD)
VRBO
From $3957 per night (USD)
VRBO
Tuscan Villa Near Florence | Vineyard Views | Pool
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Villa Vertine is a 16th-Century Tuscan villa tucked into the heart of Chianti's hillside vineyards and olive groves. It' ...
From $3957 per night (USD)
VRBO
From $151 per night (USD)
VRBO
Holiday apartment Gaiole in Chianti for 1 - 4 persons with 2 bedrooms - Holiday apartment in one or
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ED Refnr. 2763085 Quietly situated holiday residence with a shared pool and its own hand-weaving enterprise on site ...
From $151 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Holiday apartment Gaiole in Chianti for 2 - 9 persons with 4 bedrooms - Twin house
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
ED Refnr. 2762603 A delightful property situated in a peaceful location, ideal for two families or a large group of fri ...
From $316 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Holiday house Gaiole in Chianti for 2 persons with 1 bedroom - Holiday house
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ED Refnr. 2769546 Quietly situated holiday residence with a shared pool and its own hand-weaving enterprise on site ...
From $177 per night (USD)
VRBO
From $404 per night (USD)
Expedia
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 $404 per night (USD)
Expedia
$MONTELUCCI CHIANTI, GAIOLE IN CHIANTI - HOLIDAY HOUSE 8\/10 BEDS$
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VRBO
MONTELUCCI CHIANTI, GAIOLE IN CHIANTI - HOLIDAY HOUSE 8\/10 BEDS
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
MONTELUCCI CHIANTI .............. WHEREVER THE NATURE RESTS ................. PRISTINE NATURE FARM Montelucci, FROM THE ...
Click For Pricing
VRBO
From $882 per night (USD)
Expedia
Villa Radda by MMega
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
External Description Villa Radda is located in the countryside of Gaiole in Chianti. The property is accessed through a ...
From $882 per night (USD)
Expedia
From $5627 per night (USD)
VRBO
16th-Century Chianti Farmhouse by Cuvee | Vineyard & Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
WHY IT'S SPECIAL- Tucked in the vineyards in the heart of Chianti Classico, the restored farmhouse is a magical and lux ...
From $5627 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Ricavo lodge with heated pool and outdoor jacuzzi
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Lodge Ricavo is located in the heart of the Chianti Classico area, a stone's throw from Radda, Gaiole and the Chianti Ca ...
From $350 per night (USD)
Expedia
From $4644 per night (USD)
VRBO
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
Bedrooms:
9
Bathrooms:
7
Sleeps:
14
Offering panoramic vistas over Chianti’s hills and woodlands, Villa Gaiole is a serene escape in the Tuscan countryside ...
From $4644 per night (USD)
VRBO
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Expedia
Lion Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located in Bucine, this welcoming apartment lets you experience it all. You'll easily make the 8-minute drive to Vill ...
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Expedia
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VRBO
Apartment of the Guard
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located in Bucine, this welcoming apartment brings it all within your reach. You'll easily make the 8-minute drive to ...
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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 $137 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 $137 per night (USD)
VRBO
From $1635 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 $1635 per night (USD)
VRBO
From $5279 per night (USD)
VRBO
Villa Radda - 11 Guests
Bedrooms:
7
Bathrooms:
6
Sleeps:
11
VILLA RADDA - FLORENCE AREA With its beautiful medieval tower set up as a wine bar, the villa offers spectacular views a ...
From $5279 per night (USD)
VRBO
From $278 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 $278 per night (USD)
Expedia
$\Villa Erbolino\ with Private Garden, Outdoor Stone Bathtub & Wi-Fi$
From $702 per night (USD)
VRBO
\"Villa Erbolino\" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Villa Erbolino is located in Gaiole in Chianti and is the ideal accommodation for a relaxing getaway. The 2-storey b ...
From $702 per night (USD)
VRBO
From $4815 per night (USD)
VRBO
Villa Pianvecchio by Fantasia Villas
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Pianvecchio is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and o ...
From $4815 per night (USD)
VRBO
From $4796 per night (USD)
VRBO
Villa Castiglioni by Fantasia Villas
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Castiglioni is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and o ...
From $4796 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Panorama, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $115 per night (USD)
Expedia
From $258 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 $258 per night (USD)
VRBO
From $3552 per night (USD)
Expedia
VILLA CHIANTIVERTINE
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This historical ‘casa colonica’ with a fabulous 360° view has been recently restored and transformed in a luxury villa f ...
From $3552 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Holiday Apartment “Casa Dovi” in the Chianti with Fireplace & Terrace
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
The charming apartment “Casa Dovi” is situated in a rural area of the scenic Chianti region of central Italy and is perf ...
From $202 per night (USD)
VRBO
From $134 per night (USD)
VRBO
Apartment Cortona
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Farm stay in Montevarchi with an outdoor pool This farm stay features an outdoor pool and a garden. Guest accommodation ...
From $134 per night (USD)
VRBO
From $933 per night (USD)
VRBO
Podere Villole All Apartments Package Welcome to the heart of Tuscany.
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Farm stay in Montevarchi with an outdoor pool An outdoor pool and a garden are available at this farm stay. Guest accom ...
From $933 per night (USD)
VRBO
From $159 per night (USD)
VRBO
Apartment Pisa
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Farm stay in Montevarchi with an outdoor pool This farm stay features an outdoor pool. Guest accommodations at this far ...
From $159 per night (USD)
VRBO
From $159 per night (USD)
VRBO
Apartment Arezzo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Adults-only farm stay in Montevarchi with an outdoor pool This farm stay features an outdoor pool. Guest accommodations ...
From $159 per night (USD)
VRBO
From $222 per night (USD)
VRBO
Apartment Siena
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Close to cross-country skiing, ecotours, and more, this pet-friendly vacation home brings it all within reach. With c ...
From $222 per night (USD)
VRBO
From $231 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 $231 per night (USD)
VRBO
From $402 per night (USD)
Expedia
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The holiday home 'Chianti Summer' is located in Gaiole in Chianti and is the ideal accommodation for a relaxing getaway. ...
From $402 per night (USD)
Expedia
From $6927 per night (USD)
VRBO
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Bedrooms:
14
Bathrooms:
15
Sleeps:
28
Wonderful Resort located in the heart of Chianti Classico, only 30 minutes from Siena, the nearest large city and 15 mi ...
From $6927 per night (USD)
VRBO
From $160 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 4 persons with 1 bedroom - Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ED Refnr. 2899841 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are pa ...
From $160 per night (USD)
VRBO
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VRBO
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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VRBO
From $150 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 $150 per night (USD)
VRBO
From $4409 per night (USD)
VRBO
Luxury Villa in Tuscany for 10 People
Bedrooms:
8
Bathrooms:
5
Sleeps:
10
Every season is perfect for a trip to Chianti, that hilly area of Tuscany world famous for its picturesque landscapes an ...
From $4409 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 ...
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Expedia
From $123 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 3 persons with 1 bedroom - Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
ED Refnr. 2899865 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are pa ...
From $123 per night (USD)
VRBO
From $89 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 2 persons with 1 bedroom - Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ED Refnr. 2899842 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are pa ...
From $89 per night (USD)
VRBO
$Stunning private villa with pool, WIFI, A\/C, TV, patio, panoramic view and parking, close to Siena$
From $220 per night (USD)
VRBO
Stunning private villa with pool, WIFI, A\/C, TV, patio, panoramic view and parking, close to Siena
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Conveniently located 710 m (2323 ft) from Villa A Sesta, Italy in the tourist area "Siena And Surroundings" and only 22 ...
From $220 per night (USD)
VRBO
From $143 per night (USD)
Expedia
Villa Ersilia - Apartment Chianti Classico Gallo Nero
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to ecotours, parasailing, and more, this smoke-free villa brings it all within reach. With convenient onsite pa ...
From $143 per night (USD)
Expedia
From $235 per night (USD)
VRBO
SPLENDID! 3BR, SWIMMING POOL, GARDEN
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in Gaiole in Chianti, this 3-bedroom, 1-bathroom apartment lets you experience it all. Fans of nature and the ...
From $235 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Holiday apartment Gaiole in Chianti for 2 - 4 persons with 2 bedrooms - Holiday house
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ED Refnr. 2757894 Apartment for 4 persons approx. 100 m² in Gaiole in Chianti, Tuscany (Chianti) Features of the prope ...
From $225 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Dream vacation in the Chianti vineyards
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Villa Casanova is a 15th century stone tower, 3 stories high, with 5 bedrooms, each lovingly decorated with Italian line ...
From $490 per night (USD)
VRBO
From $1209 per night (USD)
Expedia
Villa With Private Pool In The Heart Of The Chianti Region
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
San Piero Terre is a south-facing stone farmhouse that has been a family holiday villa for two generations. Decorated to ...
From $1209 per night (USD)
Expedia
$Beautiful villa for 16 guests with A\/C, private pool, WIFI, TV, patio, panoramic view and parking$
From $1508 per night (USD)
VRBO
Beautiful villa for 16 guests with A\/C, private pool, WIFI, TV, patio, panoramic view and parking
Bedrooms:
10
Bathrooms:
7
Sleeps:
16
La Maccinaia 14 is located 980 m (3168 ft) from San Vincenti, Italy and only 38 km (24 mi) from Siena in the tourist are ...
From $1508 per night (USD)
VRBO
From $2271 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 $2271 per night (USD)
Expedia
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VRBO
Case Domine, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Looking for splendid isolation? You’ll find it at this very private villa, alone among the vineyards of Chianti Classico ...
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VRBO
$Stunning villa for 22 guests with WIFI, private pool, A\/C, TV, panoramic view and parking$
From $1555 per night (USD)
Expedia
Stunning villa for 22 guests with WIFI, private pool, A\/C, TV, panoramic view and parking
Bedrooms:
10
Bathrooms:
11
Sleeps:
22
Borgo San Vincenti is a lovely stone building with air conditioning, private pool and WiFi internet. The property can ...
From $1555 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Hut with a view in the heart of the Chianti area with swimming pool and Jacuzzzi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Delicious ex finely restored stable, inserted in an ancient farmhouse. The property is completely independent, private p ...
From $199 per night (USD)
VRBO
From $764 per night (USD)
Expedia
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 $764 per night (USD)
Expedia
From $266 per night (USD)
VRBO
A paradise of cypress and olive trees
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to cycling, hiking trails, and more, this smoke-free vacation home brings it all within reach. Jump into your c ...
From $266 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Belvilla by OYO Villa Le Trappoline
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Holiday in the heart of Chianti Classico in Gaiole in Chianti. Authentic and charming holiday home surrounded by a garde ...
From $378 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Belvilla by OYO Farmhouse in Radda with Garden
Bedrooms:
6
Bathrooms:
2
Sleeps:
6
This 2-bedroom farmhouse in Radda In Chianti is ideal for a small family with kids. Located in Tuscany, Italy, it can ho ...
From $156 per night (USD)
VRBO
From $1726 per night (USD)
Expedia
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Located in Castelnuovo Berardenga, this welcoming villa brings it all within your reach. With convenient onsite parki ...
From $1726 per night (USD)
Expedia
From $5435 per night (USD)
VRBO
Chianti villa rental
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Villa Castiglioni is a stunning Chianti villa rental. It is situated in the Chianti region in Tuscany, an area ...
From $5435 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Villa Oliveta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Villa Oliveta’s hillside position is hard to beat, offering far-reaching views of the olive groves from which the villa ...
From $428 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Casa Perano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Imagine the perfect Chianti villa – a secluded house with private pool and fabulous 180-degree views starring a hilltop ...
From $747 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Capanna di Citerna, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Capanna di Citerna sits on the white road between patchwork vineyards producing some of the Ricasoli estates most presti ...
From $280 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to cycling, hiking trails, and more, this welcoming villa brings it all within reach. Jump into your car and ma ...
From $420 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Pet friendly home in Gaiole in Chianti
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Beautiful and spacious Tuscan villa with swimming pool. Enjoy an unforgettable and relaxing vacation in this beautifu ...
From $586 per night (USD)
Expedia
From $4370 per night (USD)
VRBO
Luxury Tuscany villa
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Villa Vecchio is a super-stylish luxury Tuscany villa on a wine estate in the heart Chianti region. Originally ...
From $4370 per night (USD)
VRBO
From $635 per night (USD)
Expedia
Cielo di Radda, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A smart villa with a private pool just a short walk from one of Tuscany’s honeypot historic towns – what more could you ...
From $635 per night (USD)
Expedia
From $1050 per night (USD)
VRBO
Casale San Vincenti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
At this luxurious villa in the Chianti hills, you can immerse yourself in a landscape of vines laden with luscious sangi ...
From $1050 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Chiantishire Lovely Cottage with Garden & Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Castelnuovo Berardenga, this welcoming apartment brings it all within your reach. There's convenient onsit ...
From $153 per night (USD)
Expedia
$Poggio Vitignano Charming Cottage W\/Pool & Parking$
From $343 per night (USD)
VRBO
Poggio Vitignano Charming Cottage W\/Pool & Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Castelnuovo Berardenga, this welcoming apartment brings it all within your reach. With convenient onsite p ...
From $343 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Chianti Villa with pool far reaching views towards the sunset in woods&vineyards
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Restored from the ruin of a typical Tuscan farmhouse this Podere sits high on a hilltop at 600 meter above sea-level (wh ...
From $566 per night (USD)
VRBO
From $687 per night (USD)
VRBO
Villa Poggiarello, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
5
Bathrooms:
7
Sleeps:
10
Make your way along an avenue of cypress trees to find Villa Poggiarello, a cluster of charming stone buildings set on a ...
From $687 per night (USD)
VRBO
From $468 per night (USD)
Expedia
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 $468 per night (USD)
Expedia
From $2038 per night (USD)
VRBO
Terra di Siena 12, Emma Villas
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
This rate includes: -Utilities: electricity - water - gas for kitchen use and hot water - weekly linen, initial and fina ...
From $2038 per night (USD)
VRBO
From $1735 per night (USD)
Expedia
San Marcellino, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Immerse yourself in the world of wine at this villa in the grounds of Rocca di Montegrossi, one of the finest wineries i ...
From $1735 per night (USD)
Expedia
From $745 per night (USD)
VRBO
Casa Boccaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Immerse yourself in the beautiful Chianti countryside at this semi-detached apartment set in a cluster of 10 private sto ...
From $745 per night (USD)
VRBO
From $669 per night (USD)
Expedia
[Little Escape] House with pool and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Bucine, this welcoming apartment brings it all within your reach. Jump into your car and make short work o ...
From $669 per night (USD)
Expedia
From $273 per night (USD)
VRBO
La Porcilaia, 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 $273 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Casa Marina, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Immerse yourself in Tuscan daily life at Casa Marina, a townhouse on a pretty street in the heart of Radda. Take up resi ...
From $228 per night (USD)
Expedia
From $11160 per night (USD)
VRBO
Villa Vigneto Estate
Bedrooms:
23
Bathrooms:
27
Sleeps:
60
Featured as the villa in Gino's Italian Escape, ITV Series aired in November 2019. Read more here Burrowed in the heart ...
From $11160 per night (USD)
VRBO
From $2619 per night (USD)
Expedia
Borgo Merlo - Nine Bedroom Villa, Sleeps 22
Bedrooms:
10
Bathrooms:
9
Sleeps:
22
You will find Borgo Merlo in the verdant Chianti hills in the heart of Tuscany. The accommodation here comprises three n ...
From $2619 per night (USD)
Expedia
From $170 per night (USD)
VRBO
La Luna, 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 $170 per night (USD)
VRBO
From $237 per night (USD)
Expedia
La Stella, 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 $237 per night (USD)
Expedia
From $2129 per night (USD)
VRBO
Casa all'Erta, villa with private pool
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Close to horse riding, this family-friendly villa brings it all within reach. With convenient onsite parking, you'll ...
From $2129 per night (USD)
VRBO
From $2214 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 $2214 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Holiday Home 'Beretone' with Mountain View, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Overlooking the mountain, the holiday home "Beretone" in Radda in Chianti impresses guests with its fantastic views. The ...
From $217 per night (USD)
VRBO
$La Serra Vitignano-Stunning Villa W\/Swimming Pool!$
From $805 per night (USD)
Expedia
La Serra Vitignano-Stunning Villa W\/Swimming Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Located in Castelnuovo Berardenga, this welcoming villa brings it all within your reach. You'll easily make the 18-mi ...
From $805 per night (USD)
Expedia
From $915 per night (USD)
VRBO
Mulino nel Chianti 10, Emma Villas
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
This rate includes: -Utilities: electricity, water, gas for cooking purposes - weekly linen, initial and final cleaning ...
From $915 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Apartment 'Villa Sofia Spa' with Private Whirlpool, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The holiday apartment "Villa Sofia Spa" is located in Gaiole in Chianti and is perfect for an unforgettable holiday with ...
From $329 per night (USD)
Expedia

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Results: 380 Rentals