Family-Friendly Vacation Rentals in Terre di Vini, Casole d'Elsa: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Casole d'Elsa
  6.  Terre di Vini

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330 Best Family Vacation Rentals in Terre di Vini (Starting from $36)

VILLA PIEVE Winery Apt
VILLA PIEVE Winery Apt
Apartment
Pievescola, Italy
0.0k from Terre di Vini center

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

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$230
Average price / night
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Charming cottage with private pool in Siena area
Charming cottage with private pool in Siena area
House
Pievescola, 53031, Italy
0.0k from Terre di Vini center

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

2 Bedrooms4 Guests
10.0

Exceptional

9 reviews

$312
Average price / night
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Casa la Pineta
Casa la Pineta
House
Pievescola, Italy
0.4k from Terre di Vini center

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

3 Bedrooms8 Guests
9.0

Fabulous

24 reviews

$92
Average price / night
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Small house with panoramic swimming pool, terrace and wi fi
Small house with panoramic swimming pool, terrace and wi fi
House
Casole d'Elsa, 53031, Italy
1.4k from Terre di Vini center

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

10.0

Exceptional

5 reviews

$140
Average price / night
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Bazzani Apartments
Bazzani Apartments
Apartment
Pievescola, Italy
1.8k from Terre di Vini center

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

4 Bedrooms12 Guests
1.0

Review score

1 reviews

$623
Average price / night
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9- Villa La Quercia
9- Villa La Quercia
Villa
Casole d'Elsa, 53031, Italy
2.5k from Terre di Vini center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$397
Average price / night
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Borgo Il Villino
Borgo Il Villino
House
Casole dʼElsa, Italy
1.8k from Terre di Vini center

Accommodations, Pools, Parking, Country houses, Cottages, Lodgings, Vacation rentals, Places to stay, Family

18 Bedrooms19 Guests
8.0

Good

25 reviews

$159
Average price / night
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superior ground floor apartment with pool view
superior ground floor apartment with pool view
House
Casole d'Elsa, 53031, Italy
2.6k from Terre di Vini center

Barbecue, Free Parking, Heater, Kitchen, Outdoor Space, Patio, Pool, TV

1 Bedroom2 Guests
6.0

Review score

2 reviews

$115
Average price / night
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Tuscan Countryside Stay
Tuscan Countryside Stay
Apartment
Casole dʼElsa, Italy
1.8k from Terre di Vini center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$36
Average price / night
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True Tuscany Siena! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
True Tuscany Siena! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Villa
Sovicille Simignano, 53018, Italy
3.2k from Terre di Vini center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

8 Bedrooms20 Guests
9.8

Exceptional

9 reviews

$1265
Average price / night
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Apartment in Tuscany with Pool and Scenic Views
Apartment in Tuscany with Pool and Scenic Views
Apartment
Casole dʼElsa, Italy
1.8k from Terre di Vini center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$49
Average price / night
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Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,children friendly,6pers
Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,children friendly,6pers
Apartment
Casole d'Elsa, 53031, Italy
3.2k from Terre di Vini center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$278
Average price / night
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Scenic Apartment in Casole d'Elsa with Pool
Scenic Apartment in Casole d'Elsa with Pool
Apartment
Casole dʼElsa, Italy
1.8k from Terre di Vini center

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

8 Bedrooms24 Guests
6.8

Good

5 reviews

$725
Average price / night
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Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,playground,sleep 6
Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,playground,sleep 6
Apartment
Casole d'Elsa, 53031, Italy
3.2k from Terre di Vini center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$257
Average price / night
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Ibiscus
Ibiscus
Apartment
Pievescola, Italy
1.8k from Terre di Vini center

Apartments, Luxury, Accommodations, Pools, Parking, 5-star, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
7.0

Good

2 reviews

$38
Average price / night
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Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,family friendly,sleep 6
Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,family friendly,sleep 6
Apartment
Casole d'Elsa, 53031, Italy
3.2k from Terre di Vini center

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

2 Bedrooms6 Guests
New to Booking
$287
Average price / night
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Tulipano
Tulipano
Apartment
Pievescola, Italy
1.8k from Terre di Vini center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, 5-star, Lodgings, Vacation rentals

1 Bedroom4 Guests
6.7

Good

3 reviews

$37
Average price / night
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Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,children friendly,5pers
Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,children friendly,5pers
Apartment
Casole d'Elsa, 53031, Italy
3.2k from Terre di Vini center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
New to Booking
$287
Average price / night
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Fresia
Fresia
Apartment
Pievescola, Italy
1.8k from Terre di Vini center

Apartments, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$114
Average price / night
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Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,family friendly,sleep 7
Lodging in Casole Elsa,Siena,pool,Wi-Fi,terrace,barbecue,family friendly,sleep 7
Apartment
Casole d'Elsa, 53031, Italy
3.2k from Terre di Vini center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$379
Average price / night
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Anthurium
Anthurium
Apartment
Pievescola, Italy
1.9k from Terre di Vini center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, 5-star, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$59
Average price / night
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Il Fienile di Simignano
Il Fienile di Simignano
Villa
Sovicille, 53018, Italy
3.5k from Terre di Vini center

Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
New to Booking
$437
Average price / night
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Casa al Gianni - La Capanna
Casa al Gianni - La Capanna
Apartment
Sovicille, 53018, Italy
3.5k from Terre di Vini center

Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
New to Booking
$138
Average price / night
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Casa al Gianni - Il Leccio
Casa al Gianni - Il Leccio
Apartment
Sovicille, 53018, Italy
3.5k from Terre di Vini center

Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
New to Booking
$184
Average price / night
Check Availability
Casa al Gianni - La Quercia
Casa al Gianni - La Quercia
Apartment
Sovicille, 53018, Italy
3.5k from Terre di Vini center

Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
Check Availability
Casa al Gianni - Il Fico
Casa al Gianni - Il Fico
Apartment
Sovicille, 53018, Italy
3.5k from Terre di Vini center

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

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$184
Average price / night
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Casa al Gianni - Olmo
Casa al Gianni - Olmo
Apartment
Sovicille, 53018, Italy
3.5k from Terre di Vini center

Barbecue, Breakfast Available, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$184
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 Terre di Vini.

Where to stay in Terre di Vini? Best neighborhoods & areas

Terre di Vini Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 330 verified family-friendly vacation rentals in Terre di Vini. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Terre di Vini vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $36 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Terre di Vini 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 Terre di Vini 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 Terre di Vini often include amenities such as Child Friendly, Balcony/Terrace, 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.