Family-Friendly Vacation Rentals in Cantalici Winery, Gaiole in Chianti: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Gaiole in Chianti
  6.  Cantalici Winery

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491 Best Family Vacation Rentals in Cantalici Winery (Starting from $82)

Chianti C'est La Vie
Chianti C'est La Vie
Apartment
Gaiole in Chianti, Italy
0.4k from Cantalici Winery center

Balcony/Terrace, Internet, Pool, Pet Friendly, Parking, Child Friendly

2 Bedrooms4 Guests
New to Booking
$246
Average price / night
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Family friendly Chianti Villa with private pool.
Family friendly Chianti Villa with private pool.
House
San Martino al Vento, 53013, Italy
0.9k from Cantalici Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms10 Guests
New to Booking
$1142
Average price / night
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Rocca Di Castagnoli
Rocca Di Castagnoli
House
Gaiole in Chianti, Italy
0.5k from Cantalici Winery center

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

18 Bedrooms35 Guests
8.4

Very Good

166 reviews

$114
Average price / night
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Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Cottage
Gaiole in Chianti, Prov. Siena, Toscana, 53031, Italy
1.0k from Cantalici Winery center

Barbecue, Crib, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
8.4

Very Good

10 reviews

$144
Average price / night
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L'Agrifoglio
L'Agrifoglio
Villa
Gaiole in Chianti, Italy
1.4k from Cantalici Winery center

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

3 Bedrooms4 Guests
9.0

Fabulous

1 reviews

$285
Average price / night
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Villa Vigneto Estate
Villa Vigneto Estate
Villa
Gaiole in Chianti, 53013, Italy
1.1k from Cantalici Winery center

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

27 Bedrooms60 Guests
New to Booking
$13283
Average price / night
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Trifoglio
Trifoglio
Villa
Gaiole in Chianti, Italy
1.4k from Cantalici Winery center

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

1 Bedroom2 Guests
New to Booking
$233
Average price / night
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Montechioccioli by Interhome
Montechioccioli by Interhome
House
Gaiole in Chianti, 53013, Italy
1.6k from Cantalici Winery center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$122
Average price / night
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Casanova di Bricciano
Casanova di Bricciano
Villa
Gaiole in Chianti, Italy
1.5k from Cantalici Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$600
Average price / night
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Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, pets allowed and panoramic view
Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, pets allowed and panoramic view
House
Rietine, 53013, Italy
1.7k from Cantalici Winery center

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

2 Bedrooms6 Guests
New to Booking
$126
Average price / night
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Holiday Home Montechioccioli-3 by Interhome
Holiday Home Montechioccioli-3 by Interhome
House
Gaiole in Chianti, Italy
1.6k from Cantalici Winery center

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

2 Bedrooms6 Guests
New to Booking
$82
Average price / night
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Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
Villa
Gaiole In Chianti, 53013, Italy
1.9k from Cantalici Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$345
Average price / night
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Holiday Home Montechioccioli-1 by Interhome
Holiday Home Montechioccioli-1 by Interhome
House
Gaiole in Chianti, Italy
1.6k from Cantalici Winery center

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

2 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$82
Average price / night
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Hut with a view in the heart of the Chianti area with swimming pool and Jacuzzzi
Hut with a view in the heart of the Chianti area with swimming pool and Jacuzzzi
House
Gaiole In Chianti, 53013, Italy
2.1k from Cantalici Winery center

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

2 Bedrooms4 Guests
New to Booking
$227
Average price / night
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Holiday Home Montechioccioli-2 by Interhome
Holiday Home Montechioccioli-2 by Interhome
House
Gaiole in Chianti, Italy
1.6k from Cantalici Winery center

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

2 Bedrooms6 Guests
9.0

Fabulous

5 reviews

$82
Average price / night
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La Fornace di Tremoleto - Villa with exclusive pool in Chianti
La Fornace di Tremoleto - Villa with exclusive pool in Chianti
Villa
Gaiole In Chianti, 53013, Italy
2.4k from Cantalici Winery center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$410
Average price / night
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Villa il Balocco
Villa il Balocco
Villa
Gaiole in Chianti, Italy
1.6k from Cantalici Winery center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$634
Average price / night
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Villa Gaiole - Seven Bedroom Villa, Sleeps 14
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
Villa
Radda in Chianti, 53013, Italy
2.7k from Cantalici Winery center

AC, Arcade, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

7 Bedrooms14 Guests
New to Booking
$4934
Average price / night
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Casina di Mello
Casina di Mello
Villa
Gaiole in Chianti, Italy
1.7k from Cantalici Winery center

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

5 Bedrooms10 Guests
New to Booking
$1273
Average price / night
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Portion Farmhouse nestled in the heart of Chianti with private pool,
Portion Farmhouse nestled in the heart of Chianti with private pool,
House
Gaiole in Chianti, 53013, Italy
2.9k from Cantalici Winery center

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

4 Bedrooms9 Guests
9.8

Exceptional

54 reviews

$283
Average price / night
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Luxury Tuscany Hillside Villa With Heated Pool Close to Chianti Towns and Siena
Luxury Tuscany Hillside Villa With Heated Pool Close to Chianti Towns and Siena
Villa
Gaiole In Chianti, 53013, Italy
2.9k from Cantalici Winery center

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

7 Bedrooms14 Guests
New to Booking
$4434
Average price / night
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Villa With Private Pool In The Heart Of The Chianti Region
Villa With Private Pool In The Heart Of The Chianti Region
Villa
Gaiole in Chianti, 53013, Italy
3.3k from Cantalici Winery center

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

6 Bedrooms12 Guests
10.0

Exceptional

16 reviews

$1190
Average price / night
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Holiday Home 'L'arco Della Fonte' with Private Terrace, Wi-Fi and Air Conditioning
Holiday Home 'L'arco Della Fonte' with Private Terrace, Wi-Fi and Air Conditioning
House
Gaiole in Chianti, 53013, Italy
3.5k from Cantalici Winery center

AC, Barbecue, Extra Bed, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
8.0

Good

3 reviews

$121
Average price / night
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Villa Vertine | 16th Century Villa w/ Tuscany & Vineyard Views, Heated Pool
Villa Vertine | 16th Century Villa w/ Tuscany & Vineyard Views, Heated Pool
House
Vertine, 53013, Italy
3.5k from Cantalici Winery center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Extra Bed, Fireplace, Free Parking

5 Bedrooms10 Guests
New to Booking
$4466
Average price / night
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Sestuccia is a beautiful Tuscan villa just a short distance from Gaiole in Chianti
Sestuccia is a beautiful Tuscan villa just a short distance from Gaiole in Chianti
Villa
gaiole in chianti, 53013, Italy
3.5k from Cantalici Winery center

AC, Balcony, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$852
Average price / night
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Sestuccina
Sestuccina
Villa
Gaiole In Chianti, 53013, Italy
3.5k from Cantalici Winery center

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

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$293
Average price / night
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Il Colombaio In Gaiole in Chianti, Tuscany
Il Colombaio In Gaiole in Chianti, Tuscany
Villa
Gaiole in Chianti, 53013, Italy
3.5k from Cantalici Winery center

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

4 Bedrooms8 Guests
9.4

Superb

18 reviews

$368
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 Cantalici Winery.

Where to stay in Cantalici Winery? Best neighborhoods & areas

Cantalici Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 491 verified family-friendly vacation rentals in Cantalici Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cantalici Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $82 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cantalici 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 Cantalici 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 Cantalici Winery often include amenities such as Child Friendly, Internet, and Pool. 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.