Family-Friendly Vacation Rentals in Castiglione d'Orcia, Tuscany: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
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  4.  Tuscany
  5.  Castiglione d'Orcia

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293 Best Family Vacation Rentals in Castiglione d'Orcia (Starting from $76)

Santa Margherita
Santa Margherita
House
Castiglione d'Orcia, Tuscany, Italy
0.3k from Castiglione d'Orcia center

Kitchen, Oceanfront, View, Balcony/Terrace, Laundry, Tv, Guest Services

2 Bedrooms6 Guests
9.3

Superb

15 reviews

$86
Average price / night
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Independent residence with 4 apartaments and pool in val d'Orcia
Independent residence with 4 apartaments and pool in val d'Orcia
Villa
Castiglione d'Orcia, 53023, Italy
0.5k from Castiglione d'Orcia center

Barbecue, Fireplace, Free Parking, Internet, Kitchen, Outdoor Space, Pool, TV

6 Bedrooms12 Guests
New to Booking
$691
Average price / night
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Agriturismo Il Pozzo
Agriturismo Il Pozzo
Apartment
Castiglione dʼOrcia, Italy
0.3k from Castiglione d'Orcia center

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

2 Bedrooms5 Guests
9.7

Exceptional

119 reviews

$101
Average price / night
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Wonderful private villa with WIFI, private pool, A/C and panoramic view, close to Montalcino
Wonderful private villa with WIFI, private pool, A/C and panoramic view, close to Montalcino
Villa
Castiglione D'orcia, 53023, Italy
1.6k from Castiglione d'Orcia center

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

3 Bedrooms8 Guests
9.8

Exceptional

24 reviews

$540
Average price / night
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La Valle Del Sole - Val D'Orcia
La Valle Del Sole - Val D'Orcia
House
Castiglione dʼOrcia, Italy
0.5k from Castiglione d'Orcia center

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

4 Bedrooms24 Guests
9.0

Fabulous

1 reviews

$76
Average price / night
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Casa Frati by Interhome
Casa Frati by Interhome
House
Castiglione d'Orcia, 53023, Italy
2.7k from Castiglione d'Orcia center

Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

4 Bedrooms10 Guests
9.6

Exceptional

12 reviews

$458
Average price / night
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Appartamento Gemma Bianca-tavoleto
Appartamento Gemma Bianca-tavoleto
Apartment
Castiglione dʼOrcia, Italy
1.6k from Castiglione d'Orcia center

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

2 Bedrooms5 Guests
8.2

Very Good

13 reviews

$118
Average price / night
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Agriturismo 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi
Agriturismo 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi
Villa
Castiglione d'Orcia, 53023, Italy
3.0k from Castiglione d'Orcia center

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

2 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$322
Average price / night
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Appartamento Gemma Verde-tavoleto
Appartamento Gemma Verde-tavoleto
Apartment
Castiglione dʼOrcia, Italy
1.6k from Castiglione d'Orcia center

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

2 Bedrooms7 Guests
8.6

Fabulous

11 reviews

$188
Average price / night
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Casa Claudia in Val d'Orcia  alle pendici dell'Amiata a due passi dalle Terme
Casa Claudia in Val d'Orcia alle pendici dell'Amiata a due passi dalle Terme
Apartment
Campiglia D'orcia, 53023, Italy
3.1k from Castiglione d'Orcia center

Barbecue, Crib, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

25 reviews

$137
Average price / night
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Casale Santa Francesca by PosarelliVillas
Casale Santa Francesca by PosarelliVillas
Villa
Campiglia dʼOrcia, Italy
2.2k from Castiglione d'Orcia center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

8 Bedrooms16 Guests
9.0

Fabulous

1 reviews

$184
Average price / night
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Villa Sarta - Tuscan country villa with private pool
Villa Sarta - Tuscan country villa with private pool
Villa
Pienza, 53023, Italy
3.3k from Castiglione d'Orcia center

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

6 Bedrooms16 Guests
New to Booking
$658
Average price / night
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Poggio Bicchieri
Poggio Bicchieri
House
Campiglia dʼOrcia, Italy
2.5k from Castiglione d'Orcia center

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

2 Bedrooms7 Guests
9.2

Superb

7 reviews

$80
Average price / night
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WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Villa
CASTIGLIONE D'ORCIA (SI), 53023, Italy
3.5k from Castiglione d'Orcia center

AC, Arcade, Babysitting, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace

4 Bedrooms8 Guests
10.0

Exceptional

50 reviews

$1126
Average price / night
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Podere Travagliola
Podere Travagliola
House
Castiglione d'Orcia, Tuscany, Italy
2.5k from Castiglione d'Orcia center

Oceanfront, Air Conditioner, View, Smoking, Sports/Activities, Balcony/Terrace, Guest Services

1 Bedroom4 Guests
9.5

Superb

8 reviews

$142
Average price / night
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Farmhouse with pool in the heart of Val d'Orcia - Apartment 3 + 1
Farmhouse with pool in the heart of Val d'Orcia - Apartment 3 + 1
Apartment
castiglione d'orcia, 53023, Italy
3.6k from Castiglione d'Orcia center

Balcony, Barbecue, Breakfast Available, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet

1 Bedroom3 Guests
New to Booking
$212
Average price / night
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Villa Casa Frati by Interhome
Villa Casa Frati by Interhome
Villa
Castiglione dʼOrcia, Italy
2.7k from Castiglione d'Orcia center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

4 Bedrooms10 Guests
9.8

Exceptional

6 reviews

$188
Average price / night
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Three-room apartment San Marcello
Three-room apartment San Marcello
Apartment
castiglione d'orcia, 53023, Italy
3.6k from Castiglione d'Orcia center

Barbecue, Breakfast Available, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$335
Average price / night
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Terre di GIORGIO Agriturismo Villa la Palazzetta
Terre di GIORGIO Agriturismo Villa la Palazzetta
House
Castiglione dʼOrcia, Italy
2.8k from Castiglione d'Orcia center

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

8 Bedrooms10 Guests
9.1

Superb

329 reviews

$157
Average price / night
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Holiday House in Castiglione D'orcia with pool, large Garden and beautiful view
Holiday House in Castiglione D'orcia with pool, large Garden and beautiful view
Villa
castiglione d'orcia, 53023, Italy
4.0k from Castiglione d'Orcia center

Breakfast Available, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

6 Bedrooms17 Guests
New to Booking
$673
Average price / night
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Agriturismo Podere Casella
Agriturismo Podere Casella
House
Castiglione d'Orcia, Tuscany, Italy
2.8k from Castiglione d'Orcia center

View, Internet, Pet Friendly, Security/Safety, Parking, Child Friendly

2 Bedrooms4 Guests
8.8

Fabulous

107 reviews

$106
Average price / night
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Appartamento Trilocale Villa Andrea
Appartamento Trilocale Villa Andrea
Apartment
Castiglione d'Orcia, 53023, Italy
4.0k from Castiglione d'Orcia center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
New to Booking
$414
Average price / night
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'...a delicious farmhouse in the countryside where only the wind blows...'
'...a delicious farmhouse in the countryside where only the wind blows...'
Villa
Campiglia d'Orcia, 53023, Italy
4.5k from Castiglione d'Orcia center

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

6 Bedrooms16 Guests
10.0

Exceptional

7 reviews

$1071
Average price / night
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Casale d'Orcia In Castiglione d'orcia - Tuscany
Casale d'Orcia In Castiglione d'orcia - Tuscany
Villa
Castiglione d'Orcia, 53023, Italy
4.7k from Castiglione d'Orcia center

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

6 Bedrooms16 Guests
10.0

Exceptional

3 reviews

$921
Average price / night
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Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Villa
Castiglione d'Orcia, 53023, Italy
4.7k from Castiglione d'Orcia center

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

6 Bedrooms15 Guests
9.8

Exceptional

12 reviews

$654
Average price / night
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WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA
WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA
Villa
Toscana, 53023, Italy
4.7k from Castiglione d'Orcia center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater

7 Bedrooms14 Guests
10.0

Exceptional

37 reviews

$1140
Average price / night
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Podere Vignalunga is 48 hectares property with 2 main villas plus 2 annex
Podere Vignalunga is 48 hectares property with 2 main villas plus 2 annex
House
Castiglione d'Orcia, 53023, Italy
4.8k from Castiglione d'Orcia center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Hot Tub

11 Bedrooms22 Guests
New to Booking
$7064
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 Castiglione d'Orcia.

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Frequently Asked Questions

You can explore 293 verified family-friendly vacation rentals in Castiglione d'Orcia. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Castiglione d'Orcia vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $76 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Castiglione d'Orcia 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 Castiglione d'Orcia 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 Castiglione d'Orcia often include amenities such as Child Friendly, Fireplace/Heating, and Pet Friendly. 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.