Family-Friendly Vacation Rentals in Piancastagnaio, Tuscany: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Piancastagnaio

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112 Best Family Vacation Rentals in Piancastagnaio (Starting from $88)

Casale I Cascetti
Casale I Cascetti
Villa
Piancastagnaio, Italy
2.3k from Piancastagnaio center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

7 Bedrooms12 Guests
9.2

Superb

7 reviews

$598
Average price / night
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Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
Villa
Siena, 53025, Italy
2.0k from Piancastagnaio center

Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Outdoor Space, Pool, Toys

7 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$940
Average price / night
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La Torretta
La Torretta
Apartment
Piancastagnaio, Italy
2.7k from Piancastagnaio center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

1 Bedroom4 Guests
9.2

Superb

18 reviews

$143
Average price / night
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SAN GIUSEPPE VILLA - SAN GIUSEPPE
SAN GIUSEPPE VILLA - SAN GIUSEPPE
Villa
Piancastagnaio, 53025, Italy
3.9k from Piancastagnaio center

Barbecue, Internet, Pool, Washer

11 Bedrooms24 Guests
New to Booking
$950
Average price / night
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Casa Gaudi
Casa Gaudi
House
Piancastagnaio, Italy
2.7k from Piancastagnaio center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay

1 Bedroom3 Guests
9.7

Exceptional

6 reviews

$98
Average price / night
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Podere Mezzavia in Abbadia San Salvatore ,, Toscana
Podere Mezzavia in Abbadia San Salvatore ,, Toscana
Villa
Abbadia San Salvatore, 53021, Italy
4.6k from Piancastagnaio center

Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

2 Bedrooms6 Guests
8.8

Fabulous

6 reviews

$317
Average price / night
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La Casina Verde
La Casina Verde
Apartment
Piancastagnaio, Italy
2.8k from Piancastagnaio center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms5 Guests
9.0

Fabulous

5 reviews

$135
Average price / night
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Restored farmhouse on the Tuscan hills
Restored farmhouse on the Tuscan hills
House
Abbadia San Salvatore, 53021, Italy
6.2k from Piancastagnaio center

Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.0

Fabulous

13 reviews

$154
Average price / night
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Casa Vacanze Il Torchio
Casa Vacanze Il Torchio
Apartment
Piancastagnaio, Italy
2.8k from Piancastagnaio center

Skiing, Pet Friendly, Fireplace/Heating, Child Friendly

5 Bedrooms18 Guests
7.0

Good

68 reviews

$139
Average price / night
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Homerez - Villa in Santa Fiora
Homerez - Villa in Santa Fiora
Villa
Santa Fiora, 58037, Italy
8.3k from Piancastagnaio center

Barbecue, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, Pool, TV

6 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$1582
Average price / night
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Appartamento Val d'Orcia Patri
Appartamento Val d'Orcia Patri
Apartment
Piancastagnaio, Italy
3.0k from Piancastagnaio center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Self-catering

1 Bedroom5 Guests
9.1

Superb

8 reviews

$133
Average price / night
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Casale Pievevecchia – Rustic Elegance Near Santa Fiora and Hot Springs
Casale Pievevecchia – Rustic Elegance Near Santa Fiora and Hot Springs
House
Santa Fiora, 58037, Italy
8.3k from Piancastagnaio center

Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space, Pool

6 Bedrooms12 Guests
New to Booking
$620
Average price / night
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Podere Piccini with pool in Val d'Orcia-Tuscany
Podere Piccini with pool in Val d'Orcia-Tuscany
Villa
Piancastagnaio, Italy
3.1k from Piancastagnaio center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom27 Guests
10.0

Exceptional

1 reviews

$593
Average price / night
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Villa with private pool, hot tub, air conditioning, Wi-fi in Val d'Orcia.
Villa with private pool, hot tub, air conditioning, Wi-fi in Val d'Orcia.
Villa
Radicofani, 53040, Italy
8.4k from Piancastagnaio center

AC, Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms12 Guests
9.0

Fabulous

9 reviews

$570
Average price / night
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Rosa d' Inverno
Rosa d' Inverno
House
Piancastagnaio, Italy
3.2k from Piancastagnaio center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
9.6

Exceptional

11 reviews

$112
Average price / night
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Casa della Nonna – Country escape with natural pool in Tuscany
Casa della Nonna – Country escape with natural pool in Tuscany
Apartment
Santa Fiora, 58037, Italy
9.2k from Piancastagnaio center

Barbecue, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Outdoor Space

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$103
Average price / night
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La Lamponaia
La Lamponaia
Apartment
Piancastagnaio, Italy
4.0k from Piancastagnaio center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
6.2

Good

14 reviews

$88
Average price / night
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Casa Grande – Historic and Cozy Apartment with Valley View
Casa Grande – Historic and Cozy Apartment with Valley View
Apartment
Santa Fiora, 58037, Italy
9.2k from Piancastagnaio center

Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$103
Average price / night
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Appartamenti San Giuseppe
Appartamenti San Giuseppe
Apartment
Piancastagnaio, Italy
4.0k from Piancastagnaio center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

12 Bedrooms23 Guests
9.4

Superb

22 reviews

$166
Average price / night
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Loft with flowered courtyard in Val d'Orcia Radicofani
Loft with flowered courtyard in Val d'Orcia Radicofani
Apartment
Radicofani, 53040, Italy
9.9k from Piancastagnaio center

Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$145
Average price / night
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Renee House
Renee House
House
Piancastagnaio, Italy
4.2k from Piancastagnaio center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
9.0

Fabulous

7 reviews

$90
Average price / night
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Podere Colombaio - Verbena chalet in historical Podere in Val d'Orcia
Podere Colombaio - Verbena chalet in historical Podere in Val d'Orcia
Cottage
Radicofani, 53040, Italy
9.9k from Piancastagnaio center

Free Parking, Internet, No Smoking, Pool

2 Bedrooms5 Guests
New to Booking
$383
Average price / night
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Agriturismo S. Apollinare
Agriturismo S. Apollinare
House
Piancastagnaio, Italy
5.4k from Piancastagnaio center

Breakfast, Restaurant, Guest Services, Internet, Tv, Accessibility, Pet Friendly

6 Bedrooms11 Guests
8.8

Fabulous

54 reviews

$112
Average price / night
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La casa di Chicca
La casa di Chicca
Apartment
Abbadia San Salvatore, Italy
5.6k from Piancastagnaio center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
9.6

Exceptional

54 reviews

$88
Average price / night
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Agriturismo Le Paicciole
Agriturismo Le Paicciole
House
Piancastagnaio, Tuscany, Italy
5.6k from Piancastagnaio center

Child Friendly, Restaurant, Wheelchair Accessible, Balcony/Terrace, View, Smoking, Breakfast

1 Bedroom3 Guests
9.0

Fabulous

23 reviews

$96
Average price / night
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Casa del castorino
Casa del castorino
Apartment
Abbadia San Salvatore, Italy
5.8k from Piancastagnaio center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

4 Bedrooms10 Guests
9.2

Superb

51 reviews

$147
Average price / night
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I Due Ciliegi
I Due Ciliegi
Apartment
Abbadia San Salvatore, Italy
5.8k from Piancastagnaio center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

1 Bedroom4 Guests
9.6

Exceptional

20 reviews

$108
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Piancastagnaio.

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Frequently Asked Questions

You can explore 112 verified family-friendly vacation rentals in Piancastagnaio. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Piancastagnaio vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $88 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Piancastagnaio offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Piancastagnaio are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Piancastagnaio often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.