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Castellina In Chianti Luxury Holiday Rentals

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Bedrooms

Bathrooms

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Property type

Distinctive Features

Distance from

5 mi
212 rentals in Castellina In Chianti.
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool Spa, holiday rental in Castellina In Chianti
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool Spa, holiday rental in Castellina In Chianti
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool Spa, holiday rental in Castellina In Chianti

Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool Spa

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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House in a typical village in the heart of Chianti, holiday rental in Castellina In Chianti
House in a typical village in the heart of Chianti, holiday rental in Castellina In Chianti
House in a typical village in the heart of Chianti, holiday rental in Castellina In Chianti

House in a typical village in the heart of Chianti

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury converted barn with hilltop views in chianti wine region, Tuscany, holiday rental in Castellina In Chianti
Luxury converted barn with hilltop views in chianti wine region, Tuscany, holiday rental in Castellina In Chianti
Luxury converted barn with hilltop views in chianti wine region, Tuscany, holiday rental in Castellina In Chianti

Luxury converted barn with hilltop views in chianti wine region, Tuscany

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views, holiday rental in Castellina In Chianti
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views, holiday rental in Castellina In Chianti
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views, holiday rental in Castellina In Chianti

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Holiday Rental House
11 bedrooms
12 bathrooms
Sleeps 23
Match: Sleeps
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House in a typical village in the heart of Chianti, holiday rental in Castellina In Chianti
House in a typical village in the heart of Chianti, holiday rental in Castellina In Chianti
House in a typical village in the heart of Chianti, holiday rental in Castellina In Chianti

House in a typical village in the heart of Chianti

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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detached villa with private pool and garden, holiday rental in Castellina In Chianti
detached villa with private pool and garden, holiday rental in Castellina In Chianti
detached villa with private pool and garden, holiday rental in Castellina In Chianti

detached villa with private pool and garden

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2+1BR Luxe Apart In A Beautifully Restored Tuscan Farm with Pool and Spa, holiday rental in Castellina In Chianti
2+1BR Luxe Apart In A Beautifully Restored Tuscan Farm with Pool and Spa, holiday rental in Castellina In Chianti
2+1BR Luxe Apart In A Beautifully Restored Tuscan Farm with Pool and Spa, holiday rental in Castellina In Chianti

2+1BR Luxe Apart In A Beautifully Restored Tuscan Farm with Pool and Spa

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1BR Apart In a Beautif. Restored Farm, Pool & Spa, 1st floor, 140/190cm, holiday rental in Castellina In Chianti
1BR Apart In a Beautif. Restored Farm, Pool & Spa, 1st floor, 140/190cm, holiday rental in Castellina In Chianti
1BR Apart In a Beautif. Restored Farm, Pool & Spa, 1st floor, 140/190cm, holiday rental in Castellina In Chianti

1BR Apart In a Beautif. Restored Farm, Pool & Spa, 1st floor, 140/190cm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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House with swimming pool. Medieval village in the heart of Chianti Classico, holiday rental in Castellina In Chianti
House with swimming pool. Medieval village in the heart of Chianti Classico, holiday rental in Castellina In Chianti
House with swimming pool. Medieval village in the heart of Chianti Classico, holiday rental in Castellina In Chianti

House with swimming pool. Medieval village in the heart of Chianti Classico

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Tuscan farmhouse with stunning views of Chianti countryside, holiday rental in Castellina In Chianti
Beautiful Tuscan farmhouse with stunning views of Chianti countryside, holiday rental in Castellina In Chianti
Beautiful Tuscan farmhouse with stunning views of Chianti countryside, holiday rental in Castellina In Chianti

Beautiful Tuscan farmhouse with stunning views of Chianti countryside

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Villa with private swimming pool in Tuscany, holiday rental in Castellina In Chianti
Villa with private swimming pool in Tuscany, holiday rental in Castellina In Chianti
Villa with private swimming pool in Tuscany, holiday rental in Castellina In Chianti

Villa with private swimming pool in Tuscany

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Ceccatelli In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti
Ceccatelli In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti
Ceccatelli In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti

Ceccatelli In Castellina in Chianti, Tuscany

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Santantimo In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti
Santantimo In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti
Santantimo In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti

Santantimo In Castellina in Chianti, Tuscany

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View, holiday rental in Castellina In Chianti
Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View, holiday rental in Castellina In Chianti
Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View, holiday rental in Castellina In Chianti

Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Authentic Tuscan House with an outdoor swimming pool, holiday rental in Castellina In Chianti
Authentic Tuscan House with an outdoor swimming pool, holiday rental in Castellina In Chianti
Authentic Tuscan House with an outdoor swimming pool, holiday rental in Castellina In Chianti

Authentic Tuscan House with an outdoor swimming pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Villa Arnica A: A characteristic and welcoming ancient tuscan country house, holiday rental in Castellina In Chianti
Villa Arnica A: A characteristic and welcoming ancient tuscan country house, holiday rental in Castellina In Chianti
Villa Arnica A: A characteristic and welcoming ancient tuscan country house, holiday rental in Castellina In Chianti

Villa Arnica A: A characteristic and welcoming ancient tuscan country house

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2BR apart in a beautifully restored Farm w Pool and Spa, ground floor terrace, holiday rental in Castellina In Chianti
2BR apart in a beautifully restored Farm w Pool and Spa, ground floor terrace, holiday rental in Castellina In Chianti
2BR apart in a beautifully restored Farm w Pool and Spa, ground floor terrace, holiday rental in Castellina In Chianti

2BR apart in a beautifully restored Farm w Pool and Spa, ground floor terrace

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Villa rental near Siena, holiday rental in Castellina In Chianti
Villa rental near Siena, holiday rental in Castellina In Chianti
Villa rental near Siena, holiday rental in Castellina In Chianti

Villa rental near Siena

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, holiday rental in Castellina In Chianti
Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, holiday rental in Castellina In Chianti
Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, holiday rental in Castellina In Chianti

Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti

Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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9BR, 16-23 Guests  Retreats & Family In A Beautifully Restored Farm w Spa & Pool, holiday rental in Castellina In Chianti
9BR, 16-23 Guests  Retreats & Family In A Beautifully Restored Farm w Spa & Pool, holiday rental in Castellina In Chianti
9BR, 16-23 Guests  Retreats & Family In A Beautifully Restored Farm w Spa & Pool, holiday rental in Castellina In Chianti

9BR, 16-23 Guests Retreats & Family In A Beautifully Restored Farm w Spa & Pool

Holiday Rental House
9 bedrooms
7 bathrooms
Sleeps 27
Match: Sleeps
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Ginestra, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Ginestra, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Ginestra, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti

Ginestra, Castellina in Chianti, Siena and Chianti

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Stunning private villa with A/C, WIFI, TV, terrace, pets allowed, panoramic, holiday rental in Castellina In Chianti
Stunning private villa with A/C, WIFI, TV, terrace, pets allowed, panoramic, holiday rental in Castellina In Chianti
Stunning private villa with A/C, WIFI, TV, terrace, pets allowed, panoramic, holiday rental in Castellina In Chianti

Stunning private villa with A/C, WIFI, TV, terrace, pets allowed, panoramic

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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La Misura, cottage with garden and swimming pool on the hills of Chianti, holiday rental in Castellina In Chianti
La Misura, cottage with garden and swimming pool on the hills of Chianti, holiday rental in Castellina In Chianti
La Misura, cottage with garden and swimming pool on the hills of Chianti, holiday rental in Castellina In Chianti

La Misura, cottage with garden and swimming pool on the hills of Chianti

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stone barn and house with pool and breathtaking views (Cip. 1 + Cip. 2), holiday rental in Castellina In Chianti
Stone barn and house with pool and breathtaking views (Cip. 1 + Cip. 2), holiday rental in Castellina In Chianti
Stone barn and house with pool and breathtaking views (Cip. 1 + Cip. 2), holiday rental in Castellina In Chianti

Stone barn and house with pool and breathtaking views (Cip. 1 + Cip. 2)

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Villa "San Bartolomeo" with Pool and Wi-Fi - Pets allowed, holiday rental in Castellina In Chianti
Villa "San Bartolomeo" with Pool and Wi-Fi - Pets allowed, holiday rental in Castellina In Chianti
Villa "San Bartolomeo" with Pool and Wi-Fi - Pets allowed, holiday rental in Castellina In Chianti

Villa "San Bartolomeo" with Pool and Wi-Fi - Pets allowed

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa il Cipresso, in the heart of Chianti with swimming pool, holiday rental in Castellina In Chianti
Casa il Cipresso, in the heart of Chianti with swimming pool, holiday rental in Castellina In Chianti
Casa il Cipresso, in the heart of Chianti with swimming pool, holiday rental in Castellina In Chianti

Casa il Cipresso, in the heart of Chianti with swimming pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Antico Roseto - cottage with swimming pool, holiday rental in Castellina In Chianti
Casa Antico Roseto - cottage with swimming pool, holiday rental in Castellina In Chianti
Casa Antico Roseto - cottage with swimming pool, holiday rental in Castellina In Chianti

Casa Antico Roseto - cottage with swimming pool

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Belvedere cottage with swimming pool in the heart of Chianti, holiday rental in Castellina In Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti, holiday rental in Castellina In Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti, holiday rental in Castellina In Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Apartment in the heart of Chianti, holiday rental in Castellina In Chianti
Apartment in the heart of Chianti, holiday rental in Castellina In Chianti
Apartment in the heart of Chianti, holiday rental in Castellina In Chianti

Apartment in the heart of Chianti

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Chianti hilltop house, exceptional views, large swimming pool, holiday rental in Castellina In Chianti
Charming Chianti hilltop house, exceptional views, large swimming pool, holiday rental in Castellina In Chianti
Charming Chianti hilltop house, exceptional views, large swimming pool, holiday rental in Castellina In Chianti

Charming Chianti hilltop house, exceptional views, large swimming pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Casale la Canonica, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Casale la Canonica, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Casale la Canonica, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti

Casale la Canonica, Castellina in Chianti, Siena and Chianti

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
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Villa Montespertoli In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti
Villa Montespertoli In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti
Villa Montespertoli In Castellina in Chianti, Tuscany, holiday rental in Castellina In Chianti

Villa Montespertoli In Castellina in Chianti, Tuscany

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani, holiday rental in Castellina In Chianti
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani, holiday rental in Castellina In Chianti
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani, holiday rental in Castellina In Chianti

Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cignanbianco - Alba e Tramonto by Interhome, holiday rental in Castellina In Chianti
Cignanbianco - Alba e Tramonto by Interhome, holiday rental in Castellina In Chianti
Cignanbianco - Alba e Tramonto by Interhome, holiday rental in Castellina In Chianti

Cignanbianco - Alba e Tramonto by Interhome

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Old farm in the heart of Chianti Merlot apartment, holiday rental in Castellina In Chianti
Old farm in the heart of Chianti Merlot apartment, holiday rental in Castellina In Chianti
Old farm in the heart of Chianti Merlot apartment, holiday rental in Castellina In Chianti

Old farm in the heart of Chianti Merlot apartment

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casale Cipressi, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Casale Cipressi, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
Casale Cipressi, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti

Casale Cipressi, Castellina in Chianti, Siena and Chianti

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Cerretino Tettoia by Interhome, holiday rental in Castellina In Chianti
Cerretino Tettoia by Interhome, holiday rental in Castellina In Chianti
Cerretino Tettoia by Interhome, holiday rental in Castellina In Chianti

Cerretino Tettoia by Interhome

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti, holiday rental in Castellina In Chianti

La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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"LA CAPANNA" APARTMENT, holiday rental in Castellina In Chianti
"LA CAPANNA" APARTMENT, holiday rental in Castellina In Chianti
"LA CAPANNA" APARTMENT, holiday rental in Castellina In Chianti

"LA CAPANNA" APARTMENT

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Casale Il Poggino by Interhome, holiday rental in Castellina In Chianti
Casale Il Poggino by Interhome, holiday rental in Castellina In Chianti
Casale Il Poggino by Interhome, holiday rental in Castellina In Chianti

Casale Il Poggino by Interhome

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Le Macine - farmhouse with pool in Chianti, holiday rental in Castellina In Chianti
Le Macine - farmhouse with pool in Chianti, holiday rental in Castellina In Chianti
Le Macine - farmhouse with pool in Chianti, holiday rental in Castellina In Chianti

Le Macine - farmhouse with pool in Chianti

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lupinati Farm - La Corte, holiday rental in Castellina In Chianti
Lupinati Farm - La Corte, holiday rental in Castellina In Chianti
Lupinati Farm - La Corte, holiday rental in Castellina In Chianti

Lupinati Farm - La Corte

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful private villa for 4 people with WIFI, pool, TV, terrace, panoramic, holiday rental in Castellina In Chianti
Beautiful private villa for 4 people with WIFI, pool, TV, terrace, panoramic, holiday rental in Castellina In Chianti
Beautiful private villa for 4 people with WIFI, pool, TV, terrace, panoramic, holiday rental in Castellina In Chianti

Beautiful private villa for 4 people with WIFI, pool, TV, terrace, panoramic

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Villa with A/C, WIFI, private pool, TV, patio, panoramic view, close, holiday rental in Castellina In Chianti
Private Villa with A/C, WIFI, private pool, TV, patio, panoramic view, close, holiday rental in Castellina In Chianti
Private Villa with A/C, WIFI, private pool, TV, patio, panoramic view, close, holiday rental in Castellina In Chianti

Private Villa with A/C, WIFI, private pool, TV, patio, panoramic view, close

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18, holiday rental in Castellina In Chianti
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18, holiday rental in Castellina In Chianti
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18, holiday rental in Castellina In Chianti

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

Holiday Rental House
9 bedrooms
10 bathrooms
Sleeps 18
Match: Sleeps
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Villa la Corte Comfortable holiday residence, holiday rental in Castellina In Chianti
Villa la Corte Comfortable holiday residence, holiday rental in Castellina In Chianti
Villa la Corte Comfortable holiday residence, holiday rental in Castellina In Chianti

Villa la Corte Comfortable holiday residence

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Cerretino + Tettoia by Interhome, holiday rental in Castellina In Chianti
Cerretino + Tettoia by Interhome, holiday rental in Castellina In Chianti
Cerretino + Tettoia by Interhome, holiday rental in Castellina In Chianti

Cerretino + Tettoia by Interhome

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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CLASSIC BILO 3 APARTMENT, holiday rental in Castellina In Chianti
CLASSIC BILO 3 APARTMENT, holiday rental in Castellina In Chianti
CLASSIC BILO 3 APARTMENT, holiday rental in Castellina In Chianti

CLASSIC BILO 3 APARTMENT

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Typical farmhouse in the heart of Chianti with private swimming pool, holiday rental in Castellina In Chianti
Typical farmhouse in the heart of Chianti with private swimming pool, holiday rental in Castellina In Chianti
Typical farmhouse in the heart of Chianti with private swimming pool, holiday rental in Castellina In Chianti

Typical farmhouse in the heart of Chianti with private swimming pool

Holiday Rental House
13 bedrooms
12 bathrooms
Sleeps 24
Match: Sleeps
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