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

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

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571 Best Family Vacation Rentals in Pienza (Starting from $95)

Villa Fonte all'Oppio con area piscina recintata
Villa Fonte all'Oppio con area piscina recintata
Villa
Pienza, Tuscany, Italy
0.5k from Pienza center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

10 Bedrooms21 Guests
8.9

Fabulous

47 reviews

$116
Average price / night
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Splendid farmhouse in the heart of the Val d'Orcia
Splendid farmhouse in the heart of the Val d'Orcia
Villa
Pienza, 53026, Italy
1.2k from Pienza center

AC, Barbecue, Fireplace, Free Parking, Internet, Kitchen, Laundry, Microwave, Outdoor Space

7 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$889
Average price / night
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Agriturismo Marinello
Agriturismo Marinello
House
Pienza, Italy
1.1k from Pienza center

Cheap, Accommodations, Pools, Farm stays, Parking, Romantic, Cottages, Lodgings, Vacation rentals

6 Bedrooms16 Guests
9.5

Superb

668 reviews

$222
Average price / night
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Villa in Monticchiello with pool,Airconditioning,BBQ,Garten,Table tennis,sleep14
Villa in Monticchiello with pool,Airconditioning,BBQ,Garten,Table tennis,sleep14
House
Monticchiello, 53026, Italy
1.3k from Pienza center

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

7 Bedrooms14 Guests
New to Booking
$823
Average price / night
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Agriturismo Barbi
Agriturismo Barbi
House
Monticchiello, Italy
1.3k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

8 Bedrooms28 Guests
9.1

Superb

306 reviews

$155
Average price / night
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Il Podere di Casa Rossa Pienza
Il Podere di Casa Rossa Pienza
Apartment
Pienza, 53026, Italy
1.5k from Pienza center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$293
Average price / night
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Agriturismo il Casato Mag-il Giogo
Agriturismo il Casato Mag-il Giogo
House
Pienza, Italy
1.4k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Places to stay, Accessible hotels

2 Bedrooms9 Guests
9.4

Superb

20 reviews

$392
Average price / night
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Private Villa with A/C, private pool, internet, TV, patio, panoramic view, close to Montepulciano
Private Villa with A/C, private pool, internet, TV, patio, panoramic view, close to Montepulciano
Villa
Monticchiello, 53026, Italy
1.7k from Pienza center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

7 Bedrooms14 Guests
New to Booking
$1172
Average price / night
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Podere Casa Rossa a Pienza
Podere Casa Rossa a Pienza
Apartment
Pienza, Italy
1.5k from Pienza center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Jacuzzis, Places to stay, Family

4 Bedrooms8 Guests
9.9

Exceptional

7 reviews

$283
Average price / night
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Beautiful villa with swimming pool in Val d'Orcia
Beautiful villa with swimming pool in Val d'Orcia
Villa
Pienza, 53026, Italy
1.7k from Pienza center

Barbecue, Extra Bed, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

6 Bedrooms12 Guests
New to Booking
$2099
Average price / night
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Agriturismo il Casato Mag-il Vaglio
Agriturismo il Casato Mag-il Vaglio
House
Pienza, Italy
1.5k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Places to stay, Accessible hotels

2 Bedrooms5 Guests
8.9

Fabulous

21 reviews

$245
Average price / night
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Finestra Dell'Angelo
Finestra Dell'Angelo
Apartment
Pienza, 53026, Italy
1.8k from Pienza center

Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$157
Average price / night
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Agriturismo il Casato - il Torchio
Agriturismo il Casato - il Torchio
House
Pienza, Italy
1.5k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Places to stay, Accessible hotels

1 Bedroom5 Guests
9.4

Superb

31 reviews

$222
Average price / night
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Samsara Apartment elegant apartment in the historical center.
Samsara Apartment elegant apartment in the historical center.
Apartment
Pienza, 53026, Italy
2.0k from Pienza center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
New to Booking
$211
Average price / night
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Suite Gioconda a Pienza
Suite Gioconda a Pienza
House
Pienza, Italy
1.5k from Pienza center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

2 Bedrooms4 Guests
9.4

Superb

17 reviews

$320
Average price / night
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Wonderful private villa for 8 guests with A/C, WIFI, TV and veranda, close to Montepulciano
Wonderful private villa for 8 guests with A/C, WIFI, TV and veranda, close to Montepulciano
Villa
Monticchiello, 53026, Italy
2.0k from Pienza center

AC, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$525
Average price / night
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Agriturismo Santa Maria
Agriturismo Santa Maria
House
Pienza, Italy
1.6k from Pienza center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals

7 Bedrooms13 Guests
9.8

Exceptional

68 reviews

$99
Average price / night
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Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Apartment
Pienza, 53026, Italy
2.0k from Pienza center

Heater, Internet, Kitchen, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$168
Average price / night
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Agriturismo Casalpiano
Agriturismo Casalpiano
House
Pienza, Italy
1.6k from Pienza center

Cheap, Accommodations, Pools, Farm stays, Parking, Romantic, Cottages, Lodgings, Vacation rentals

6 Bedrooms12 Guests
9.5

Superb

161 reviews

$95
Average price / night
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Lovely apartment in villa for 2 people with WIFI, A/C, close to Montepulciano
Lovely apartment in villa for 2 people with WIFI, A/C, close to Montepulciano
House
Monticchiello, 53026, Italy
2.2k from Pienza center

AC, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$359
Average price / night
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Agriturismo Podere Chiassaie
Agriturismo Podere Chiassaie
House
Monticchiello, Italy
1.7k from Pienza center

View, Parking, Fireplace/Heating, Child Friendly

3 Bedrooms8 Guests
9.1

Superb

19 reviews

$130
Average price / night
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Lovely apartment in villa for 6 people with WIFI, A/C, TV and veranda, close to Montepulciano
Lovely apartment in villa for 6 people with WIFI, A/C, TV and veranda, close to Montepulciano
House
Monticchiello, 53026, Italy
2.3k from Pienza center

AC, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$659
Average price / night
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Apartment in Monticchiello with 2 bedrooms sleeps 4
Apartment in Monticchiello with 2 bedrooms sleeps 4
Apartment
Monticchiello, 53026, Italy
2.3k from Pienza center

AC, Barbecue, Crib, Fireplace, Heater, Internet, Kitchen, Laundry, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$191
Average price / night
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Nice apartment for 4 guests with WIFI, A/C and TV, close to Montepulciano
Nice apartment for 4 guests with WIFI, A/C and TV, close to Montepulciano
Apartment
Monticchiello, 53026, Italy
2.3k from Pienza center

AC, Barbecue, Crib, Fireplace, Heater, Internet, Kitchen, Laundry, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$232
Average price / night
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Casa Bonari, amazing Tuscan view
Casa Bonari, amazing Tuscan view
Apartment
Monticchiello, 53026, Italy
2.4k from Pienza center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$190
Average price / night
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Maria Gabriella Holiday Home
Maria Gabriella Holiday Home
Villa
Monticchiello, 53026, Italy
2.5k from Pienza center

AC, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$460
Average price / night
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Maria Gabriella Home
Maria Gabriella Home
House
Monticchiello, 53026, Italy
2.5k from Pienza center

AC, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$579
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 Pienza.

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Frequently Asked Questions

You can explore 571 verified family-friendly vacation rentals in Pienza. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Pienza vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $95 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Pienza 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 Pienza 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 Pienza often include amenities such as Fireplace/Heating, Child Friendly, 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.