Family-Friendly Vacation Rentals in San Casciano in Val di Pesa, Tuscany: Compare 10+ Sites & Save

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546 Best Family Vacation Rentals in San Casciano in Val di Pesa (Starting from $52)

Pozzo Dei Desideri by PosarelliVillas
Pozzo Dei Desideri by PosarelliVillas
House
San Casciano in Val di Pesa, Tuscany, Italy
1.0k from San Casciano in Val di Pesa center

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

4 Bedrooms10 Guests
8.7

Fabulous

15 reviews

$99
Average price / night
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Villa in Paolini with 6 bedrooms sleeps 15
Villa in Paolini with 6 bedrooms sleeps 15
Villa
Paolini, 50026, Italy
0.6k from San Casciano in Val di Pesa center

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

8 Bedrooms15 Guests
New to Booking
$3008
Average price / night
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Castello di Bibbione
Castello di Bibbione
House
San Casciano in Val di Pesa, Italy
1.3k from San Casciano in Val di Pesa center

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

12 Bedrooms28 Guests
9.2

Superb

445 reviews

$82
Average price / night
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Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location
Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location
Villa
San Casciano Val di Pesa, 50026, Italy
0.6k from San Casciano in Val di Pesa center

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

3 Bedrooms8 Guests
9.6

Exceptional

18 reviews

$989
Average price / night
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Le Massucce
Le Massucce
House
San Casciano in Val di Pesa, Italy
1.5k from San Casciano in Val di Pesa center

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

5 Bedrooms13 Guests
8.6

Fabulous

32 reviews

$52
Average price / night
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[VILLA ACQUAPIETRA FLORENCE⭐⭐⭐⭐⭐] Pool | Vineyards | Olive trees
[VILLA ACQUAPIETRA FLORENCE⭐⭐⭐⭐⭐] Pool | Vineyards | Olive trees
Villa
San Casciano Val di Pesa, 50026, Italy
0.8k from San Casciano in Val di Pesa center

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

7 Bedrooms16 Guests
8.0

Good

3 reviews

$1195
Average price / night
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Salvadonica
Salvadonica
House
San Casciano in Val di Pesa, Italy
1.7k from San Casciano in Val di Pesa center

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

30 Bedrooms23 Guests
9.3

Superb

1202 reviews

$341
Average price / night
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Apartment House with garden Tuscany Chianti ,  Florence 15km.
Apartment House with garden Tuscany Chianti , Florence 15km.
House
Toscana, 50026, Italy
0.9k from San Casciano in Val di Pesa center

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

2 Bedrooms5 Guests
9.8

Exceptional

74 reviews

$174
Average price / night
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La Porta Rossa
La Porta Rossa
House
San Casciano in Val di Pesa, Italy
1.8k from San Casciano in Val di Pesa center

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

1 Bedroom3 Guests
9.3

Superb

23 reviews

$83
Average price / night
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country house with garden ,pool,children's play area ,Tuscany,15 from Florence
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
House
Toscana, 50026, Italy
0.9k from San Casciano in Val di Pesa center

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

2 Bedrooms5 Guests
9.8

Exceptional

82 reviews

$149
Average price / night
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Porta del Chianti Tuscany Apartment
Porta del Chianti Tuscany Apartment
Apartment
San Casciano in Val di Pesa, Italy
1.8k from San Casciano in Val di Pesa center

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

1 Bedroom4 Guests
9.4

Superb

52 reviews

$119
Average price / night
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Beautiful independent villa with private swimming pool
Beautiful independent villa with private swimming pool
Villa
San Casciano in Val di Pesa, 50026, Italy
1.4k from San Casciano in Val di Pesa center

Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms12 Guests
New to Booking
$1054
Average price / night
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Relais Poggio Borgoni
Relais Poggio Borgoni
House
San Casciano in Val di Pesa, Italy
1.8k from San Casciano in Val di Pesa center

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

10 Bedrooms12 Guests
9.3

Superb

569 reviews

$281
Average price / night
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the chianti tower
the chianti tower
House
San Casciano In Val di Pesa, 50026, Italy
1.6k from San Casciano in Val di Pesa center

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

2 Bedrooms3 Guests
10.0

Exceptional

2 reviews

$165
Average price / night
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Appartamento Mandiri
Appartamento Mandiri
Apartment
San Casciano in Val di Pesa, Italy
1.9k from San Casciano in Val di Pesa center

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

2 Bedrooms5 Guests
9.3

Superb

37 reviews

$88
Average price / night
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Wonderful private villa for 9 guests with WIFI, hot tub, TV, patio and panoramic view
Wonderful private villa for 9 guests with WIFI, hot tub, TV, patio and panoramic view
House
San Casciano In Val Di Pesa, 50026, Italy
1.7k from San Casciano in Val di Pesa center

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

5 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$438
Average price / night
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Appartamento Ilesis
Appartamento Ilesis
Apartment
San Casciano in Val di Pesa, Italy
1.9k from San Casciano in Val di Pesa center

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

2 Bedrooms4 Guests
9.0

Fabulous

12 reviews

$118
Average price / night
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Villa Badessa in Tuscany by Fantasia Villas
Villa Badessa in Tuscany by Fantasia Villas
Villa
Toscana, 50020, Italy
1.9k from San Casciano in Val di Pesa center

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

6 Bedrooms15 Guests
New to Booking
$1969
Average price / night
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Flò Country Suite
Flò Country Suite
Apartment
San Casciano in Val di Pesa, Italy
1.9k from San Casciano in Val di Pesa center

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

3 Bedrooms5 Guests
9.5

Superb

2 reviews

$563
Average price / night
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VILLA VAL DI PESA_Villa Acquapietra - VILLA VAL DI PESA
VILLA VAL DI PESA_Villa Acquapietra - VILLA VAL DI PESA
Villa
San Casciano in Val di Pesa, 50026, Italy
2.0k from San Casciano in Val di Pesa center

AC, Barbecue, Dryer, Fireplace, Free Parking, Internet, Microwave, Pool, Washer

7 Bedrooms17 Guests
New to Booking
$2255
Average price / night
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la Torretta di Villa Borri Chianti Classico
la Torretta di Villa Borri Chianti Classico
Apartment
San Casciano in Val di Pesa, Italy
1.9k from San Casciano in Val di Pesa center

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

2 Bedrooms4 Guests
7.5

Good

9 reviews

$81
Average price / night
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Villa il Giglio in Chianti 20 Min from Florence
Villa il Giglio in Chianti 20 Min from Florence
House
San Casciano in Val di Pesa, 50026, Italy
2.0k from San Casciano in Val di Pesa center

Barbecue, Crib, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$372
Average price / night
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Our charming Tuscan Cottage
Our charming Tuscan Cottage
Cottage
Toscana, 50026, Italy
2.1k from San Casciano in Val di Pesa center

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

2 Bedrooms4 Guests
New to Booking
$375
Average price / night
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The colors of Chianti
The colors of Chianti
House
Mercatale In Val di Pesa, 50020, Italy
2.2k from San Casciano in Val di Pesa center

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

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$194
Average price / night
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Il Convento by Interhome
Il Convento by Interhome
Apartment
Montefiridolfi, 50026, Italy
2.3k from San Casciano in Val di Pesa center

Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$143
Average price / night
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A Charming Country House in the Tuscan Chianti with pool and gardens
A Charming Country House in the Tuscan Chianti with pool and gardens
Villa
Toscana, 50026, Italy
2.4k from San Casciano in Val di Pesa center

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

4 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$742
Average price / night
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Lovely apartment for 6 people with WIFI, pets allowed and panoramic view
Lovely apartment for 6 people with WIFI, pets allowed and panoramic view
Apartment
San Casciano In Val Di Pesa, 50026, Italy
2.5k from San Casciano in Val di Pesa center

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

3 Bedrooms6 Guests
New to Booking
$166
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 San Casciano in Val di Pesa.

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San Casciano in Val di Pesa Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 546 verified family-friendly vacation rentals in San Casciano in Val di Pesa. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in San Casciano in Val di Pesa vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $52 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in San Casciano in Val di Pesa 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 San Casciano in Val di Pesa 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 San Casciano in Val di Pesa 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.