Family-Friendly Vacation Rentals in Castello di Radda Winery, Radda in Chianti: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Radda in Chianti
  6.  Castello di Radda Winery

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627 Best Family Vacation Rentals in Castello di Radda Winery (Starting from $116)

Tenuta Cortedomina
Tenuta Cortedomina
House
Radda in Chianti, Italy
0.5k from Castello di Radda Winery center

Guest Services, Tv, Oceanfront, Business Services, Ocean View, View, Accessibility

7 Bedrooms17 Guests
9.6

Exceptional

352 reviews

$320
Average price / night
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Escape to Vineyards, Elba
Escape to Vineyards, Elba
Apartment
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space, Patio, Pool

2 Bedrooms4 Guests
9.4

Superb

22 reviews

$241
Average price / night
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Sotto - La colonica nel Chianti
Sotto - La colonica nel Chianti
House
Castello di Radda Winery, Radda in Chianti, Tuscany, Italy
0.5k from Castello di Radda Winery center

Kitchen, Pool, Internet, Parking, Child Friendly

6 Bedrooms13 Guests
8.0

Good

1 reviews

$1990
Average price / night
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Pretty farmhouse with terrace
Pretty farmhouse with terrace
Apartment
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space, Patio

2 Bedrooms6 Guests
9.2

Superb

26 reviews

$253
Average price / night
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Sopra - La colonica nel Chianti
Sopra - La colonica nel Chianti
House
Castello di Radda Winery, Radda in Chianti, Tuscany, Italy
0.5k from Castello di Radda Winery center

Internet, Pool, Kitchen, Parking, Child Friendly

5 Bedrooms11 Guests
New to Booking
$2086
Average price / night
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Apartment in Radda with Garden
Apartment in Radda with Garden
Apartment
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

AC, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.4

Superb

21 reviews

$233
Average price / night
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Intera- La Colonica nel Chianti
Intera- La Colonica nel Chianti
House
Castello di Radda Winery, Radda in Chianti, Tuscany, Italy
0.5k from Castello di Radda Winery center

Internet, Pool, Kitchen, Parking, Child Friendly

11 Bedrooms22 Guests
New to Booking
$3993
Average price / night
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La Terrazza by Interhome
La Terrazza by Interhome
House
Radda in Chianti, 53017, Italy
1.0k from Castello di Radda Winery center

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

3 Bedrooms6 Guests
8.0

Good

5 reviews

$196
Average price / night
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Chianti Hillside Farmhouse
Chianti Hillside Farmhouse
House
Radda in Chianti, Italy
0.7k from Castello di Radda Winery center

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

6 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$2150
Average price / night
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Le Bonatte by Interhome
Le Bonatte by Interhome
House
Radda in Chianti, 53017, Italy
1.0k from Castello di Radda Winery center

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

7 Bedrooms14 Guests
New to Booking
$429
Average price / night
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La Capannina del Chianti
La Capannina del Chianti
Apartment
Toscana, 53017, Italy
1.1k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
New to Booking
$168
Average price / night
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Timeless stillness, steps from the piazza
Timeless stillness, steps from the piazza
Villa
Radda in Chianti, 53017, Italy
1.2k from Castello di Radda Winery center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms10 Guests
New to Booking
$2695
Average price / night
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A paradise of cypress and olive trees
A paradise of cypress and olive trees
House
Radda in Chianti, 53107, Italy
1.2k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

39 reviews

$270
Average price / night
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Agriturismo Borgo Il Bonagino
Agriturismo Borgo Il Bonagino
House
Radda in Chianti, Italy
0.7k from Castello di Radda Winery center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Lodgings, Vacation rentals, Places to stay

8 Bedrooms16 Guests
9.3

Superb

61 reviews

$231
Average price / night
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Villa Eterna, Tuscan Haven in the Heart of Chianti
Villa Eterna, Tuscan Haven in the Heart of Chianti
Villa
Radda in Chianti, 53017, Italy
1.3k from Castello di Radda Winery center

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

5 Bedrooms10 Guests
New to Booking
$2940
Average price / night
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Limoni
Limoni
House
Radda in Chianti, Italy
0.7k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$136
Average price / night
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Wonderful  villa for 6 people with WIFI, TV, terrace, pets allowed and panoramic view
Wonderful villa for 6 people with WIFI, TV, terrace, pets allowed and panoramic view
Villa
Radda In Chianti, 53017, Italy
1.3k from Castello di Radda Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$229
Average price / night
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Girasole
Girasole
House
Radda in Chianti, Italy
0.7k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
New to Booking
$116
Average price / night
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Il Torrino In Radda in Chianti, Tuscany
Il Torrino In Radda in Chianti, Tuscany
Villa
Radda in Chianti, 53017, Italy
1.6k from Castello di Radda Winery center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$927
Average price / night
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Uva
Uva
House
Radda in Chianti, Italy
0.7k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
New to Booking
$127
Average price / night
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Cottage \"Podere in Volpaia\" with Garden & Wi-Fi
Cottage \"Podere in Volpaia\" with Garden & Wi-Fi
Cottage
Radda in Chianti, 53017, Italy
1.6k from Castello di Radda Winery center

AC, Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$277
Average price / night
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Villa del Poggio by Interhome
Villa del Poggio by Interhome
House
Radda in Chianti, 53017, Italy
1.8k from Castello di Radda Winery center

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

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$276
Average price / night
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L'Angolino In Radda in Chianti, Tuscany
L'Angolino In Radda in Chianti, Tuscany
Villa
Radda in Chianti, 53017, Italy
1.8k from Castello di Radda Winery center

AC, Fireplace, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$317
Average price / night
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 In the heart of Chianti: view over the valley, relaxation & art, wine & sun
In the heart of Chianti: view over the valley, relaxation & art, wine & sun
House
Radda in Chianti (SI), 53017, Italy
1.9k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

66 reviews

$153
Average price / night
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Villa in Volpaia with 6 bedrooms sleeps 12
Villa in Volpaia with 6 bedrooms sleeps 12
Villa
Volpaia, 53017, Italy
1.9k from Castello di Radda Winery center

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

6 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$1150
Average price / night
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Villa in Volpaia with 4 bedrooms sleeps 8
Villa in Volpaia with 4 bedrooms sleeps 8
Villa
Volpaia, 53017, Italy
1.9k from Castello di Radda Winery center

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

4 Bedrooms8 Guests
New to Booking
$932
Average price / night
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Private Villa with WIFI, private pool, TV, terrace, panoramic view, close to Greve In Chianti
Private Villa with WIFI, private pool, TV, terrace, panoramic view, close to Greve In Chianti
Villa
Volpaia, 53017, Italy
2.0k from Castello di Radda Winery center

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

6 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$1482
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 Castello di Radda Winery.

Where to stay in Castello di Radda Winery? Best neighborhoods & areas

Castello di Radda Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 627 verified family-friendly vacation rentals in Castello di Radda Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Castello di Radda Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $116 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Castello di Radda Winery 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 Castello di Radda Winery 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 Castello di Radda Winery often include amenities such as Child Friendly, Internet, and Kitchen. 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.