1. What are the top vacation rentals in Val di Chiana?

There are a lot of options in Val di Chiana. If you plan on staying in the Val di Chiana area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Val di Chiana:

2. How many vacation rentals have private pools in Val di Chiana?

There are 0 vacation rentals with private pools near Val di Chiana. Top-rated homes that have access to a swimming pool include:

3. Which vacation homes in Val di Chiana are best for families?

If you are looking for a family-friendly vacation home in Val di Chiana, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Val di Chiana:

4. How many vacation rentals are available in Val di Chiana?

Currently, the total number of properties listed in 2025 is over 14 in the Val di Chiana area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Val di Chiana.

Book the Best Places to Stay in Val di Chiana

Find Curated Vacation Rentals, Boutique Cabins, and Stylish Eco-Friendly Acommodation in Val di Chiana

From US $157

10.0 (8 Reviews)

Apartment

Ciliano 16

Parking
Security/Safety
Sports/Activities

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From US $268

10.0 (4 Reviews)

House

Podere San Giuseppe

Air Conditioner
Parking
Pool

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Macadamia Tuscany House - Studio apartment in the green, bordering Val d'Orcia

From US $139

New

Apartment

Macadamia Tuscany House - Studio apartment in the green, bordering Val d'Orcia

Air Conditioner
Parking
Pet Friendly

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From US $113

9.8 (35 Reviews)

Bed & Breakfast

Al Giardino degli Etruschi

Parking
Pool
Balcony/Terrace

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Panorama and infinity pool in the Siena Province, south of Montepulciano

From US $696

10.0 (77 Reviews)

Villa

Panorama and infinity pool in the Siena Province, south of Montepulciano

Air Conditioner
Parking
Pool

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From US $213

9.6 (23 Reviews)

House

B&B Fonteroncone

Air Conditioner
Parking
Pool

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Very cute apartment in the core of Old Montepulciano with strong wi fi fiber

From US $84

9.8 (35 Reviews)

Apartment

Very cute apartment in the core of Old Montepulciano with strong wi fi fiber

Parking
Security/Safety
Bedding/Linens

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From US $129

8.8 (48 Reviews)

Other

Agriturismo La Pietriccia

Air Conditioner
Parking
Pool

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Fornace del Conte - Apartment mit 2 Schlafzimmern

From US $269

New

Apartment

Fornace del Conte - Apartment mit 2 Schlafzimmern

Parking
Pool
View

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From US $110

8.8 (249 Reviews)

Hotel

Hotel Panoramic

Parking
Pool
TV

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Charming Ground-Floor Apartment just steps from Montepulciano's Historic Center

From US $184

New

Apartment

Charming Ground-Floor Apartment just steps from Montepulciano's Historic Center

Air Conditioner
Parking
TV

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Fornace del Conte - Apartment mit 1 Schlafzimmer

From US $151

New

Apartment

Fornace del Conte - Apartment mit 1 Schlafzimmer

Parking
Pool
View

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Agriturismo Eco-Pescaia Two-bedroom apartment in Montepulciano

From US $130

10.0 (1 Review)

Other

Agriturismo Eco-Pescaia Two-bedroom apartment in Montepulciano

Air Conditioner
Parking
TV

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Farmhouse Eco-Pescaia Studio Apartment in Montepulciano

From US $130

New

Other

Farmhouse Eco-Pescaia Studio Apartment in Montepulciano

Air Conditioner
Parking
TV

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★ Pro Tip: Bettertrips makes it easy to compare the best listings on Bettertrips homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bettertrips 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.