Family-Friendly Vacation Rentals in Bosco della Ragnaia, Montalcino: Compare 10+ Sites & Save

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  3.  Italy
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263 Best Family Vacation Rentals in Bosco della Ragnaia (Starting from $79)

Il Borghetto - Oliviera loft
Il Borghetto - Oliviera loft
Apartment
San Giovanni dʼAsso, Italy
0.4k from Bosco della Ragnaia center

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

1 Bedroom2 Guests
7.0

Good

2 reviews

$142
Average price / night
Check Availability
Private Villa with private pool, WIFI, A/C, TV, terrace, panoramic view, close to Montalcino
Private Villa with private pool, WIFI, A/C, TV, terrace, panoramic view, close to Montalcino
Villa
San Giovanni D'asso, 53020, Italy
0.1k from Bosco della Ragnaia center

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

8 Bedrooms14 Guests
New to Booking
$1281
Average price / night
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Il Borghetto - Oliviera Townhouse
Il Borghetto - Oliviera Townhouse
Apartment
San Giovanni dʼAsso, Italy
0.4k from Bosco della Ragnaia center

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

2 Bedrooms3 Guests
9.7

Exceptional

3 reviews

$142
Average price / night
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Beautiful private villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Montalcino
Beautiful private villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Montalcino
Villa
San Giovanni D'asso, 53020, Italy
0.2k from Bosco della Ragnaia center

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

5 Bedrooms10 Guests
New to Booking
$1462
Average price / night
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Pasqui Villas Tribbio villa con piscina vista WiFi vicino al paese
Pasqui Villas Tribbio villa con piscina vista WiFi vicino al paese
Villa
San Giovanni dʼAsso, Italy
0.4k from Bosco della Ragnaia center

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

5 Bedrooms10 Guests
New to Booking
$497
Average price / night
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Villa \"Casa Luisa\"\nvery welcoming apartment, pets are allowed
Villa \"Casa Luisa\"\nvery welcoming apartment, pets are allowed
Apartment
San Giovanni d'Asso, 53020, Italy
0.5k from Bosco della Ragnaia center

Balcony, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$123
Average price / night
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Ca' Montalcino
Ca' Montalcino
Apartment
San Giovanni dʼAsso, Italy
0.5k from Bosco della Ragnaia center

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

1 Bedroom3 Guests
8.4

Very Good

18 reviews

$79
Average price / night
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Pasqui Villas:  Capanna ,country chic house in a village: garden,pool,view,WIFi
Pasqui Villas: Capanna ,country chic house in a village: garden,pool,view,WIFi
House
San Giovanni d'Asso, 53024, Italy
0.5k from Bosco della Ragnaia center

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

3 Bedrooms6 Guests
New to Booking
$381
Average price / night
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VAL D'ORCIA DELUXE 1 ELEGANTE CASA immersa nel verde con WiFi, giardino e parcheggio
VAL D'ORCIA DELUXE 1 ELEGANTE CASA immersa nel verde con WiFi, giardino e parcheggio
Apartment
San Giovanni dʼAsso, Italy
0.5k from Bosco della Ragnaia center

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

4 Bedrooms8 Guests
9.3

Superb

36 reviews

$160
Average price / night
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Pasqui Villas Il Tribbio, San Giovanni d'Asso-Montalcino, 53024, IT
Pasqui Villas Il Tribbio, San Giovanni d'Asso-Montalcino, 53024, IT
Villa
San Giovanni d'Asso-Montalcino, 53024, Italy
0.5k from Bosco della Ragnaia center

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

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$924
Average price / night
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VAL D'ORCIA DELUXE 2, RAFFINATA CASA immersa nel verde con WiFi, giardino e parcheggio
VAL D'ORCIA DELUXE 2, RAFFINATA CASA immersa nel verde con WiFi, giardino e parcheggio
Apartment
Montalcino, Italy
0.5k from Bosco della Ragnaia center

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

1 Bedroom9 Guests
8.9

Fabulous

34 reviews

$137
Average price / night
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 Pasqui Villas Historic Villa La Consuma San Giovanni D'Asso-Italy
Pasqui Villas Historic Villa La Consuma San Giovanni D'Asso-Italy
Villa
SAN GIOVANNI D'ASSO, 53024, Italy
0.5k from Bosco della Ragnaia center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Hot Tub, Housekeeping, Internet

8 Bedrooms16 Guests
New to Booking
$853
Average price / night
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Pasqui Villas La Consuma villa storica in paese con vista pscina WiFi
Pasqui Villas La Consuma villa storica in paese con vista pscina WiFi
Villa
San Giovanni dʼAsso, Italy
0.5k from Bosco della Ragnaia center

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

8 Bedrooms14 Guests
New to Booking
$976
Average price / night
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INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY
INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY
Villa
San Giovanni d'Asso, 53020, Italy
0.7k from Bosco della Ragnaia center

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

5 Bedrooms10 Guests
9.8

Exceptional

37 reviews

$596
Average price / night
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VAL D'ORCIA DELUXE 3 incantevole casa con vista sulle colline, WiFi e parcheggio
VAL D'ORCIA DELUXE 3 incantevole casa con vista sulle colline, WiFi e parcheggio
House
San Giovanni dʼAsso, Italy
0.6k from Bosco della Ragnaia center

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

4 Bedrooms7 Guests
9.7

Exceptional

22 reviews

$181
Average price / night
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Wonderful private villa with A/C, private pool, WIFI, TV, patio, panoramic view, close to Montalcino
Wonderful private villa with A/C, private pool, WIFI, TV, patio, panoramic view, close to Montalcino
House
San Giovanni D'asso, 53024, Italy
1.0k from Bosco della Ragnaia center

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

3 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$635
Average price / night
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Cottage Casa Luisa
Cottage Casa Luisa
Apartment
Montalcino, Italy
0.6k from Bosco della Ragnaia center

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

4 Bedrooms9 Guests
9.5

Superb

4 reviews

$120
Average price / night
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Stunning private villa with A/C, WIFI, private pool, TV, patio, panoramic view, close to Montalcino
Stunning private villa with A/C, WIFI, private pool, TV, patio, panoramic view, close to Montalcino
Villa
San Giovanni D'asso, 53020, Italy
1.0k from Bosco della Ragnaia center

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

6 Bedrooms12 Guests
New to Booking
$3332
Average price / night
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Pasqui Villas La Capanna accogliente casa in paese con vista piscina WiFi
Pasqui Villas La Capanna accogliente casa in paese con vista piscina WiFi
Villa
San Giovanni dʼAsso, Italy
0.6k from Bosco della Ragnaia center

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

3 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$339
Average price / night
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Historic Villa Ferrano has modern amenities, ideal for medium-sized events.
Historic Villa Ferrano has modern amenities, ideal for medium-sized events.
Villa
Toscana, 53020, Italy
1.2k from Bosco della Ragnaia center

AC, Barbecue, Breakfast Included, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

23 Bedrooms38 Guests
10.0

Exceptional

1 reviews

$7198
Average price / night
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Alborata 10, Emma Villas
Alborata 10, Emma Villas
Villa
Montalcino, Italy
0.6k from Bosco della Ragnaia center

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

5 Bedrooms10 Guests
5.0

Review score

1 reviews

$637
Average price / night
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Recently restored Villa in Tuscany, sleeps 12, sw.pool,  gym, big garden.
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Villa
San Giovanni d' Asso, 53024, Italy
1.3k from Bosco della Ragnaia center

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

6 Bedrooms12 Guests
10.0

Exceptional

13 reviews

$2539
Average price / night
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Montalcino Villa - Breathtaking Views of the Val d'Orcia
Montalcino Villa - Breathtaking Views of the Val d'Orcia
Apartment
Montalcino, 53020, Italy
2.1k from Bosco della Ragnaia center

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

3 Bedrooms6 Guests
9.8

Exceptional

48 reviews

$417
Average price / night
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Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
House
San Giovanni d' Asso, 53020, Italy
2.1k from Bosco della Ragnaia center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$333
Average price / night
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 Tuscan dream home in the Val d'Orcia valley
Tuscan dream home in the Val d'Orcia valley
House
Montisi, 53020, Italy
2.1k from Bosco della Ragnaia center

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

2 Bedrooms5 Guests
9.2

Superb

29 reviews

$281
Average price / night
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Country House in Crete Senesi between Siena and Val d'Orcia Area
Country House in Crete Senesi between Siena and Val d'Orcia Area
House
Asciano, 53041, Italy
3.0k from Bosco della Ragnaia center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Outdoor Space, Patio

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$506
Average price / night
Check Availability
  Montalcino,private villa with pool in Tuscany,stunning wiews!
Montalcino,private villa with pool in Tuscany,stunning wiews!
Villa
Montisi, 53024, Italy
3.3k from Bosco della Ragnaia center

Barbecue, Crib, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

7 Bedrooms15 Guests
9.8

Exceptional

17 reviews

$854
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 Bosco della Ragnaia.

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Frequently Asked Questions

You can explore 263 verified family-friendly vacation rentals in Bosco della Ragnaia. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Bosco della Ragnaia vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $79 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Bosco della Ragnaia 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 Bosco della Ragnaia 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 Bosco della Ragnaia 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.