The Best Vacation Rentals in Val di Chiana

Prepare to Relax and Experience Family Fun – The Best Vacations Happen in a Vacation Rental

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From $833

         

10.0 (48 Reviews)

Villa

Charming Villa with private pool between Pienza and Montepulciano

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Torrita di Siena

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From $48

         

|

8.5 (2 Reviews)

Apartment

Appartamento nel Centro storico

• Parking
• Pet Friendly
• Wheelchair Accessible

• Tuscany
• Lucignano

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From $243

         

|

10.0 (35 Reviews)

House

500 m² House ∙ 8 bedrooms ∙ 20 guests

• 5381 ft² House
• Parking
• Pool
• TV

• Tuscany
• Cetona

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From $1,833

         

New

Villa

Villa Ripa - My Rental Homes

• Tuscany
• Foiano della Chiana

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From $122

         

9.8 (60 Reviews)

Apartment

La Querceta, Tyypillinen Asuinpaikka. Viime Hetken Tarjous

• Parking
• Pet Friendly
• Pool

• Tuscany
• Torrita di Siena

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From $55

         

|

7.7 (7 Reviews)

House

Villa Chiara

• Parking
• Pet Friendly
• Balcony/Terrace

• Torrita di Siena
• Montefollonico

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From $182

         

|

10.0 (32 Reviews)

House

100 m² House ∙ 2 bedrooms ∙ 4 guests

• 1076 ft² House
• Parking
• Pool
• TV

• Tuscany
• Sinalunga

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From $127

         

New

Villa

Villa 'Anni '50' with Private Garden and Wi-Fi

• Pet Friendly
• TV
• Balcony/Terrace

• Tuscany
• Sarteano

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From $394

         

10.0 (34 Reviews)

Apartment

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

• Air Conditioner
• TV
• Security/Safety

• Tuscany
• Montepulciano

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From $46

         

6.0 (3 Reviews)

Apartment

Finestra sulla toscana

• Parking
• Pet Friendly
• Wheelchair Accessible

• Tuscany
• Chianciano Terme

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From $483

         

|

10.0 (30 Reviews)

House

800 m² House ∙ 10 bedrooms ∙ 20 guests

• 8611 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Foiano della Chiana

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From $316

         

10.0 (112 Reviews)

House

Il Tosco

• Air Conditioner
• Parking
• TV

• Tuscany
• Montepulciano

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From $95

         

9.6 (51 Reviews)

Apartment

LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Tuscany
• Montepulciano

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From $61

         

|

9.1 (17 Reviews)

Apartment

Bella Vista Flat

• Air Conditioner
• Parking
• Balcony/Terrace

• Trequanda
• Petroio

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From $443

         

9.4 (45 Reviews)

Villa

Villa with private pool, air conditioning near wineries at 3km from village

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Chianciano Terme

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From $75

         

|

7.5 (13 Reviews)

Apartment

La Casa di Lucia

• Parking
• Pet Friendly
• Balcony/Terrace

• Trequanda
• Castelmuzio

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From $333

         

9.4 (29 Reviews)

Villa

Villa Mario - Villa with private pool

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Lucignano

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From $35

         

|

8.7 (14 Reviews)

Apartment

I Fucoli

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Chianciano Terme

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From $487

         

9.8 (36 Reviews)

Villa

Villa Lauretana - Vacation Rental in Torrita di Siena, Tuscany

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Torrita di Siena

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From $306

         

9.7 (7 Reviews)

Villa

Casale Rosino

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Chiusi

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From $246

         

8.8 (18 Reviews)

Villa

Villa Gloria - Holiday Rental in Lucignano, Valdichiana, Tuscany

• Air Conditioner
• Parking
• Pool

• Tuscany
• Lucignano

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From $255

         

|

8.0 (2 Reviews)

Villa

Villa Palmina

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Lucignano

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From $385

         

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Villa

Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany

• Parking
• Pet Friendly
• Pool

• Tuscany
• Montepulciano

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From $1,409

         

9.6 (4 Reviews)

Villa

VILLA PALAZZO BELLO with Pool, Air Con, Wifi - Cetona

• Air Conditioner
• Parking
• Pet Friendly

• Tuscany
• Cetona

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★ Pro Tip: Vacationsrental makes it easy to compare the best listings on Vacationsrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Vacationsrental homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Val di Chiana.