Family-Friendly Vacation Rentals in Montecalvario, Castellina in Chianti: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Castellina in Chianti
  6.  Montecalvario

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638 Best Family Vacation Rentals in Montecalvario (Starting from $103)

Chianti Classico Home Panoramic View
Chianti Classico Home Panoramic View
House
Castellina in Chianti, Italy
0.2k from Montecalvario center

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

9 Bedrooms18 Guests
8.0

Good

5 reviews

$450
Average price / night
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ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Villa
Castellina in Chianti, 53011, Italy
0.0k from Montecalvario center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

11 Bedrooms23 Guests
10.0

Exceptional

64 reviews

$3564
Average price / night
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Casa Anna
Casa Anna
House
Castellina in Chianti, Italy
0.3k from Montecalvario center

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

3 Bedrooms4 Guests
8.9

Fabulous

7 reviews

$103
Average price / night
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Casa Vacanze Squarcialupi
Casa Vacanze Squarcialupi
Apartment
Via Aldo Moro, 20, Castellina in Chianti, 53011, Italy
0.5k from Montecalvario center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
8.8

Fabulous

3 reviews

$153
Average price / night
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Casa Chiara by Interhome
Casa Chiara by Interhome
House
Castellina in Chianti, 53011, Italy
0.5k from Montecalvario center

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

2 Bedrooms4 Guests
8.0

Good

1 reviews

$146
Average price / night
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Wonderful private villa for 14 guests with A/C, WIFI, private pool, TV, patio and panoramic view
Wonderful private villa for 14 guests with A/C, WIFI, private pool, TV, patio and panoramic view
Villa
Castellina In Chianti, 53011, Italy
0.7k from Montecalvario center

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

7 Bedrooms14 Guests
New to Booking
$804
Average price / night
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Palazzo Bianciardi Attico
Palazzo Bianciardi Attico
Apartment
Castellina in Chianti, Italy
0.3k from Montecalvario center

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

2 Bedrooms5 Guests
9.4

Superb

43 reviews

$158
Average price / night
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Vacation home Olivo by Interhome
Vacation home Olivo by Interhome
House
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.6

Exceptional

4 reviews

$249
Average price / night
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Holiday Home Casa Chiara by Interhome
Holiday Home Casa Chiara by Interhome
House
Castellina in Chianti, Italy
0.5k from Montecalvario center

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

2 Bedrooms4 Guests
7.4

Good

5 reviews

$148
Average price / night
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Cerretino Tettoia by Interhome
Cerretino Tettoia by Interhome
House
Castellina in Chianti, 53100, Italy
0.8k from Montecalvario center

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

2 Bedrooms4 Guests
New to Booking
$214
Average price / night
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Holiday Home Olivo by Interhome
Holiday Home Olivo by Interhome
House
Castellina in Chianti, Italy
0.7k from Montecalvario center

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

3 Bedrooms4 Guests
New to Booking
$291
Average price / night
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Cerretino group house 14 sleeps by Interhome
Cerretino group house 14 sleeps by Interhome
House
Castellina in Chianti, 53100, Italy
0.8k from Montecalvario center

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

7 Bedrooms14 Guests
New to Booking
$693
Average price / night
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Capanna Leopoldina 10
Capanna Leopoldina 10
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$707
Average price / night
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Cerretino Vigna by Interhome
Cerretino Vigna by Interhome
House
Castellina in Chianti, 53100, Italy
0.8k from Montecalvario center

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

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$172
Average price / night
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Il Nocino
Il Nocino
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$216
Average price / night
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Cerretino Oliveto by Interhome
Cerretino Oliveto by Interhome
House
Castellina in Chianti, 53100, Italy
0.8k from Montecalvario center

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

3 Bedrooms6 Guests
New to Booking
$215
Average price / night
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Capanna Leopoldina 8
Capanna Leopoldina 8
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$449
Average price / night
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Stunning private villa for 4 people with WIFI, A/C, TV, terrace and panoramic view
Stunning private villa for 4 people with WIFI, A/C, TV, terrace and panoramic view
House
Castellina In Chianti, 53011, Italy
0.9k from Montecalvario center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$169
Average price / night
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La Querce
La Querce
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

2 Bedrooms3 Guests
10.0

Exceptional

2 reviews

$190
Average price / night
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Cosy apartment in villa for 4 guests with A/C, WIFI, pool, TV, patio and panoramic view
Cosy apartment in villa for 4 guests with A/C, WIFI, pool, TV, patio and panoramic view
Villa
Castellina In Chianti, 53011, Italy
1.0k from Montecalvario center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$251
Average price / night
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Holiday Home Cerretino Tettoia by Interhome
Holiday Home Cerretino Tettoia by Interhome
House
Italy
0.8k from Montecalvario center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
7.0

Good

1 reviews

$182
Average price / night
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Cosy apartment in villa for 4 guests with pool, A/C, WIFI, TV, patio and panoramic view
Cosy apartment in villa for 4 guests with pool, A/C, WIFI, TV, patio and panoramic view
Villa
Castellina In Chianti, 53011, Italy
1.0k from Montecalvario center

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

2 Bedrooms4 Guests
New to Booking
$209
Average price / night
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Farmhouse in the heart of the real chiantishire
Farmhouse in the heart of the real chiantishire
House
Castellina in Chianti, 53011, Italy
1.2k from Montecalvario center

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

2 Bedrooms4 Guests
10.0

Exceptional

153 reviews

$177
Average price / night
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Casa Belmonte In Castellina in Chianti, Tuscany
Casa Belmonte In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
1.2k from Montecalvario center

Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Space, Pool

4 Bedrooms8 Guests
9.4

Superb

13 reviews

$536
Average price / night
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Agriturismo with pool and view close to the center of Castellina in Chianti
Agriturismo with pool and view close to the center of Castellina in Chianti
House
Castellina in Chianti, 53011, Italy
1.4k from Montecalvario center

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

1 Bedroom4 Guests
9.8

Exceptional

95 reviews

$195
Average price / night
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FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
Villa
Castellina in Chianti, 53011, Italy
1.4k from Montecalvario center

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

6 Bedrooms13 Guests
9.8

Exceptional

32 reviews

$1322
Average price / night
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Authentic Stone House with Pool & Scenic Views – Perfect for Nature Lovers
Authentic Stone House with Pool & Scenic Views – Perfect for Nature Lovers
House
Castellina in Chianti, 53011, Italy
1.4k from Montecalvario center

Balcony, Barbecue, Breakfast Available, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$283
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 Montecalvario.

Where to stay in Montecalvario? Best neighborhoods & areas

Montecalvario Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 638 verified family-friendly vacation rentals in Montecalvario. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Montecalvario vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $103 per night, with larger homes and peak travel periods often costing more.

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