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

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  3.  Italy
  4.  Tuscany
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265 Best Family Vacation Rentals in Montalcino (Starting from $93)

CASA DI ELENA
CASA DI ELENA
Apartment
Montalcino, Italy
0.2k from Montalcino center

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

2 Bedrooms4 Guests
9.3

Superb

48 reviews

$202
Average price / night
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Classic, Private Villa with Breathtaking Views - Private Pool
Classic, Private Villa with Breathtaking Views - Private Pool
Villa
montalcino, 99999, Italy
2.2k from Montalcino center

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

4 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$660
Average price / night
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Casa per l'Osticcio con Vista Panoramica
Casa per l'Osticcio con Vista Panoramica
Apartment
Montalcino, Italy
0.2k from Montalcino center

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

2 Bedrooms5 Guests
8.9

Fabulous

22 reviews

$188
Average price / night
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Sibilla Guest House, home in the heart of Val d'Orcia
Sibilla Guest House, home in the heart of Val d'Orcia
Apartment
Torrenieri, 53024, Italy
5.6k from Montalcino center

AC, Balcony, Breakfast Included, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$104
Average price / night
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Montalcino numero10
Montalcino numero10
Apartment
Montalcino, Italy
0.2k from Montalcino center

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

2 Bedrooms7 Guests
9.5

Superb

2 reviews

$93
Average price / night
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Cerretalta - Country villa with private pool
Cerretalta - Country villa with private pool
Villa
San Quirico D'orcia, 53024, Italy
5.9k from Montalcino center

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

7 Bedrooms14 Guests
10.0

Exceptional

9 reviews

$816
Average price / night
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CASA COSTA DELLE CASERME
CASA COSTA DELLE CASERME
Apartment
Montalcino, Italy
0.2k from Montalcino center

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

1 Bedroom2 Guests
8.6

Fabulous

48 reviews

$178
Average price / night
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Beautiful private villa with A/C, private pool, WIFI, TV, patio, panoramic view, close to Montalcino
Beautiful private villa with A/C, private pool, WIFI, TV, patio, panoramic view, close to Montalcino
Villa
San Quirico D'orcia, 53024, Italy
6.0k from Montalcino center

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

7 Bedrooms14 Guests
10.0

Exceptional

11 reviews

$885
Average price / night
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Casa Mustiola
Casa Mustiola
House
Montalcino, Tuscany, Italy
0.2k from Montalcino center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

4 Bedrooms11 Guests
9.0

Fabulous

127 reviews

$136
Average price / night
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Your home in Tuscany, in the land of Brunello
Your home in Tuscany, in the land of Brunello
House
Montalcino, 53024, Italy
6.8k from Montalcino center

Balcony, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, TV

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$180
Average price / night
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Palazzo Tamanti - 4BR Estate Home
Palazzo Tamanti - 4BR Estate Home
Villa
Montalcino, Italy
0.3k from Montalcino center

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

4 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$683
Average price / night
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Beautiful apartment in villa with pool, WIFI, TV, terrace, pets allowed and panoramic view
Beautiful apartment in villa with pool, WIFI, TV, terrace, pets allowed and panoramic view
Villa
San Giovanni D'asso, 53024, Italy
7.4k from Montalcino center

Crib, Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space, Pool, TV

2 Bedrooms6 Guests
New to Booking
$269
Average price / night
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Anna Camere
Anna Camere
House
Montalcino, Tuscany, Italy
0.3k from Montalcino center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

8 Bedrooms7 Guests
8.6

Fabulous

484 reviews

$115
Average price / night
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FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA
FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA
Apartment
Buonconvento, 53022, Italy
7.7k from Montalcino center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

1 Bedroom3 Guests
10.0

Exceptional

37 reviews

$226
Average price / night
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La casa di Annetta
La casa di Annetta
Apartment
Montalcino, Italy
0.3k from Montalcino center

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

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$122
Average price / night
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FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO LEZIONI DI CUCINA
FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO LEZIONI DI CUCINA
Apartment
Buonconvento, 53022, Italy
7.7k from Montalcino center

AC, Barbecue, Crib, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub

1 Bedroom3 Guests
9.8

Exceptional

31 reviews

$230
Average price / night
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Podere Il Lampo
Podere Il Lampo
House
Montalcino, Italy
0.3k from Montalcino center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Self-catering

3 Bedrooms8 Guests
9.4

Superb

46 reviews

$324
Average price / night
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Cozy farmhouse near Montalcino
Cozy farmhouse near Montalcino
Villa
San Giovanni d'Asso, 53020, Italy
7.7k from Montalcino center

Barbecue, Fireplace, Free Parking, Laundry, TV, Washer

4 Bedrooms7 Guests
New to Booking
$210
Average price / night
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Tuscany View Montalcino
Tuscany View Montalcino
House
Montalcino, Italy
0.3k from Montalcino center

B&bs, Accommodations, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

5 Bedrooms5 Guests
8.8

Fabulous

272 reviews

$166
Average price / night
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VILLA CERRETO - Seven Bedroom Villa, Sleeps 14
VILLA CERRETO - Seven Bedroom Villa, Sleeps 14
Villa
Montalcino, 53022, Italy
7.9k from Montalcino center

AC, Free Parking, Heater, Kitchen, Living Area, No Smoking, Outdoor Space, Pool, Washer

8 Bedrooms14 Guests
New to Booking
$2310
Average price / night
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In centro
In centro
Apartment
Montalcino, Italy
0.3k from Montalcino center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms5 Guests
8.9

Fabulous

67 reviews

$184
Average price / night
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Villa Aiale, 7 En-Suite Bdrs, AC Throughout, Private Pool – Wine Estate
Villa Aiale, 7 En-Suite Bdrs, AC Throughout, Private Pool – Wine Estate
Villa
Buonconvento, 53022, Italy
8.3k from Montalcino center

AC, Barbecue, Crib, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

7 Bedrooms14 Guests
10.0

Exceptional

5 reviews

$1665
Average price / night
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Goccia in Valdorcia Smart Home
Goccia in Valdorcia Smart Home
Apartment
San Quirico d'Orcia, 53027, Italy
8.5k from Montalcino center

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

3 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$107
Average price / night
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Stunning estate + winery operating as two luxury villas + infinity pool
Stunning estate + winery operating as two luxury villas + infinity pool
House
Bibbiano, 53022, Italy
8.5k from Montalcino center

AC, Breakfast Included, Extra Bed, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Living Area

16 Bedrooms38 Guests
New to Booking
$12669
Average price / night
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Villa di Montesoli - Buonconvento
Villa di Montesoli - Buonconvento
Villa
Buonconvento, 53022, Italy
8.7k from Montalcino center

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

9 Bedrooms18 Guests
New to Booking
$2961
Average price / night
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Stunning private villa for 16 guests with private pool, A/C, WIFI, TV, patio and panoramic view
Stunning private villa for 16 guests with private pool, A/C, WIFI, TV, patio and panoramic view
Villa
Montalcino, 53024, Italy
8.7k from Montalcino center

AC, Balcony, Barbecue, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet

8 Bedrooms16 Guests
New to Booking
$2203
Average price / night
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Villa in Montalcino with 8 bedrooms sleeps 16
Villa in Montalcino with 8 bedrooms sleeps 16
Villa
Montalcino, 53024, Italy
8.8k from Montalcino center

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

8 Bedrooms16 Guests
New to Booking
$1556
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 Montalcino.

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Montalcino Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 265 verified family-friendly vacation rentals in Montalcino. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Montalcino vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $93 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Montalcino 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 Montalcino 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 Montalcino 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.