Holiday Homes in Val di Chiana

Find your dream holiday home and book one of 13 vacation rentals
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August 2026
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Selected Holiday Homes in Val di Chiana

RecommendedGuestsReviewBedroomsStarsPrice (ascending)Price (descending)
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4.1 (8)
Valiano

Cottage Toskanischer Rückzugsort mit Pool

6 Bedrooms

Fast Responder
Free cancellation
€1,862.55
2 guests / 7 Nights
Property image
4.7 (6)
Trevinano

Holiday house Toskanisches Refugium mit Pool

1 Bedrooms

€1,455.86
2 guests / 7 Nights
Property image
4.0 (4)
San Casciano dei Bagni

Holiday house Komplett renovierter Bauernhof für 2 Personen in der Toskana

1 Bedrooms

€783.36
2 guests / 7 Nights
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5.0 (3)
Montepulciano

Holiday house Casa Nobile

2 Bedrooms

€1,499.98
2 guests / 7 Nights
Hidden GemHidden Gem
Property image
4.8 (1)
San Casciano dei Bagni

Holiday house Geräumiges Ferienhaus in Paizze mit eigenem Pool

6 Bedrooms

€2,719.63
2 guests / 7 Nights
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3.0 (1)
San Casciano dei Bagni

Holiday house Elegant Tuscan Holiday Home

2 Bedrooms

€2,885.51
2 guests / 7 Nights

Holiday ideas

Not sure where to go? Explore perfect holiday ideas!

Taking your dog on holiday - 12 Apartments & Holiday Homes

Taking your dog on holiday

12 Accommodations
Taking your pet on holiday - 11 Apartments & Holiday Homes

Taking your pet on holiday

11 Accommodations
Family friendly - 3 Apartments & Holiday Homes

Family friendly

3 Accommodations
Swimming pool - 3 Apartments & Holiday Homes

Swimming pool

3 Accommodations
Wine growing regions - 3 Apartments & Holiday Homes

Wine growing regions

3 Accommodations
Cheap vacation apartments - 2 Apartments & Holiday Homes

Cheap vacation apartments

2 Accommodations

Accommodations with Washing Machine

Property image
4.1 (8)
Valiano

Cottage Toskanischer Rückzugsort mit Pool

6 Bedrooms

Fast Responder
Free cancellation
€1,862.55
2 guests / 7 Nights
Property image
5.0 (3)
Montepulciano

Holiday house Casa Nobile

2 Bedrooms

€1,499.98
2 guests / 7 Nights
Hidden GemHidden Gem

Accommodations with Swimming Pool

Property image
4.1 (8)
Valiano

Cottage Toskanischer Rückzugsort mit Pool

6 Bedrooms

Fast Responder
Free cancellation
€1,862.55
2 guests / 7 Nights
Property image
4.7 (6)
Trevinano

Holiday house Toskanisches Refugium mit Pool

1 Bedrooms

€1,455.86
2 guests / 7 Nights
Property image
5.0 (3)
Montepulciano

Holiday house Casa Nobile

2 Bedrooms

€1,499.98
2 guests / 7 Nights
Hidden GemHidden Gem
Property image
4.8 (1)
San Casciano dei Bagni

Holiday house Geräumiges Ferienhaus in Paizze mit eigenem Pool

6 Bedrooms

€2,719.63
2 guests / 7 Nights

Most searched amenities in Val di Chiana

Swimming Pool13 Holiday homes
Washing Machine6 Holiday homes
WiFi12 Holiday homes
Dishwasher9 Holiday homes
Terrace8 Holiday homes
Television11 Holiday homes

Holiday Homes in Val di Chiana

Cetona

Chiusi

Montepulciano

San Casciano dei Bagni

Sinalunga

Trevinano

Valiano

Our ideas for your dream holiday in Val di Chiana

Cheap vacation apartments in Val di Chiana
Family friendly in Val di Chiana
Group accommodation in Val di Chiana
Riding holiday in Val di Chiana
Secluded location in Val di Chiana
Swimming pool in Val di Chiana
Taking your dog on holiday in Val di Chiana
Taking your pet on holiday in Val di Chiana
Wine growing regions in Val di Chiana
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