Chianti Region Villas

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Top Villas in Chianti Region

Villa with concierge service & heated pool at 20 minute from Florence center

Villa with concierge service & heated pool at 20 minute from Florence center

impruneta Toscana
$1,606 nightly
The price is $1,610 total per night
$1,610 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
An outdoor pool is featured at this villa, along with free WiFi in public areas and a terrace. Families will appreciate the onsite laundry facilities and babysitting. Limo/town car service, a garden, and concierge services are also on offer.
Pool
Kitchen
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Montespertoli Toscana
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This villa features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Impruneta (Florence) Tuscany
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This villa features an outdoor pool and a hot tub. Families will appreciate the playground, onsite laundry facilities, and childcare. A garden and barbecue grills are also provided.
Pool
Hot Tub
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Santa Cristina in Salivolpe Tuscany
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This villa features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. A terrace, limo/town car service, and a garden are also on offer.
Pool
Hot Tub
Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti

Località Vegi 16 Castellina in Chianti SI
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A seasonal outdoor pool is featured at this villa, along with a garden.
Pool
Kitchen
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

San Casciano in Val di Pesa Tuscany
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This villa features an outdoor pool and a gym. Families will appreciate the onsite laundry facilities and childcare. A terrace, a garden, and concierge services are also on offer.
Pool
Kitchen
Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena

Fonterutoli Provincia di Siena
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This villa features laundry facilities.
Washer
Dryer
Villa Orchidea - Historical villa with pool

Villa Orchidea - Historical villa with pool

San Donnino Tuscany
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This villa features a garden, a library, and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

Radda in Chianti Italy
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An outdoor pool is featured at this villa, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Pool
Kitchen
Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.

Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.

Figline Valdarno Tuscany
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This villa includes a garden and laundry facilities.
Pool
Kitchen
Home Cinema • Private Pool & Hot Tub • Sleeps 12 (6 Bathrooms)

Home Cinema • Private Pool & Hot Tub • Sleeps 12 (6 Bathrooms)

Pergine
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This villa features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti

La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti

Località Canonica 16 Greve in Chianti FI
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A 24-hour gym is featured at this villa, along with a terrace and a garden. Barbecue grills are provided for your convenience.
Kitchen
Washer
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See all available properties in Chianti Region
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Chianti Region

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Via Roma 191 Barberino Tavarnelle FI
$71 nightly
The price is $86 total per night from Dec 8 to Dec 9
$86 total
Dec 8 - Dec 9
Total with taxes and fees
9.4/10 Exceptional! (471 reviews)

Chianti Region Villas essential information

Accommodation
600 Villas
Lowest Price
$55
Highest Price
$1,610
Popular accommodation
Villa with concierge service & heated pool at 20 minute from Florence center, Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi, Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City, Villa Salivolpe - on top of a Chianti hill - Private swimming pool , Luxury Villa Basilio Chianti, Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C., Private villa in the heart of chianti with view of siena, Villa Orchidea - Historical villa with pool, 4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC, Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside., Home Cinema • Private Pool & Hot Tub • Sleeps 12 (6 Bathrooms), La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti

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