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

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  San Casciano in Val di Pesa
  6.  Il Serraglio

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578 Best Family Vacation Rentals in Il Serraglio (Starting from $52)

Sassaia Nel Chianti
Sassaia Nel Chianti
Apartment
San Casciano in Val di Pesa, Italy
0.1k from Il Serraglio center

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

1 Bedroom5 Guests
7.0

Good

1 reviews

$231
Average price / night
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Chianti family villa, 5 bedrooms, infinity pool, A/C, EV charger, BBQ, 360° view
Chianti family villa, 5 bedrooms, infinity pool, A/C, EV charger, BBQ, 360° view
Villa
San casciano val di Pesa, 50026, Italy
0.1k from Il Serraglio center

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

5 Bedrooms10 Guests
9.8

Exceptional

35 reviews

$777
Average price / night
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Tenuta Il Corno Agriturismo
Tenuta Il Corno Agriturismo
House
San Casciano in Val di Pesa, Italy
0.5k from Il Serraglio center

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

11 Bedrooms34 Guests
8.9

Fabulous

113 reviews

$159
Average price / night
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Villa air conditioning, pool, electric cars, ideal location in Chianti
Villa air conditioning, pool, electric cars, ideal location in Chianti
House
San Casciano in Val di Pesa, 50026, Italy
0.2k from Il Serraglio center

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

4 Bedrooms8 Guests
New to Booking
$781
Average price / night
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Villa Salivolpe Amazing Chianti View
Villa Salivolpe Amazing Chianti View
Apartment
Le Fornacette, Italy
1.1k from Il Serraglio center

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

9 Bedrooms18 Guests
New to Booking
$642
Average price / night
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Apartment 'Sassaia' with Private Pool, Wi-Fi, and Air Conditioning
Apartment 'Sassaia' with Private Pool, Wi-Fi, and Air Conditioning
Apartment
San Casciano in Val di pesa, 50026, Italy
0.4k from Il Serraglio center

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

1 Bedroom4 Guests
New to Booking
$553
Average price / night
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Archipettoli
Archipettoli
Villa
San Casciano in Val di Pesa, Italy
1.1k from Il Serraglio center

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

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$400
Average price / night
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Archipettoli - a historical manor house with stunning panoramic views
Archipettoli - a historical manor house with stunning panoramic views
Villa
Firenze, 50026, Italy
1.1k from Il Serraglio center

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

6 Bedrooms12 Guests
10.0

Exceptional

37 reviews

$916
Average price / night
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Polvereto
Polvereto
Apartment
Le Fornacette, Italy
1.2k from Il Serraglio center

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

1 Bedroom4 Guests
New to Booking
$136
Average price / night
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Getaway Amidst Vineyards
Getaway Amidst Vineyards
House
Montespertoli, 50025, Italy
1.6k from Il Serraglio center

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

2 Bedrooms4 Guests
9.0

Fabulous

16 reviews

$135
Average price / night
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Private Room in Chianti Shared Home
Private Room in Chianti Shared Home
House
San Pancrazio, Italy
1.4k from Il Serraglio center

Accommodations, Parking, Homestays, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$56
Average price / night
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Au Coeur du Chianti
Au Coeur du Chianti
House
montespertoli, 50025, Italy
1.8k from Il Serraglio center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$192
Average price / night
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Tuscan Haven with Pool
Tuscan Haven with Pool
House
San Casciano in Val di Pesa, 50026, Italy
1.9k from Il Serraglio center

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

1 Bedroom3 Guests
8.6

Fabulous

19 reviews

$214
Average price / night
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Corzano e Paterno
Corzano e Paterno
House
San Casciano in Val di Pesa, Italy
1.6k from Il Serraglio center

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

21 Bedrooms42 Guests
9.7

Exceptional

27 reviews

$516
Average price / night
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Holiday Home with Vineyard Vibes
Holiday Home with Vineyard Vibes
House
San Casciano in Val di Pesa, 50026, Italy
1.9k from Il Serraglio center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms3 Guests
9.0

Fabulous

20 reviews

$212
Average price / night
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Casa Rossa
Casa Rossa
Apartment
Polvereto, Italy
1.6k from Il Serraglio center

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

2 Bedrooms4 Guests
8.2

Very Good

36 reviews

$105
Average price / night
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Holiday Home in Tuscany with Vineyards
Holiday Home in Tuscany with Vineyards
House
San Casciano in Val di Pesa, 50026, Italy
1.9k from Il Serraglio center

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

2 Bedrooms3 Guests
9.2

Superb

22 reviews

$205
Average price / night
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Bio-Agriturismo La Ginestra
Bio-Agriturismo La Ginestra
House
San Casciano in Val di Pesa, Italy
1.8k from Il Serraglio center

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

8 Bedrooms24 Guests
9.1

Superb

247 reviews

$52
Average price / night
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Cottage in Tuscany with Pool & BBQ
Cottage in Tuscany with Pool & BBQ
House
San Casciano in Val di Pesa, 50026, Italy
1.9k from Il Serraglio center

Barbecue, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Pool, Toys

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$175
Average price / night
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Agriturismo Sant'Ellero
Agriturismo Sant'Ellero
House
San Casciano in Val di Pesa, Italy
1.8k from Il Serraglio center

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

2 Bedrooms5 Guests
8.9

Fabulous

45 reviews

$147
Average price / night
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Tuscan Vineyard Farm Stay
Tuscan Vineyard Farm Stay
House
San Casciano in Val di Pesa, 50026, Italy
1.9k from Il Serraglio center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms5 Guests
9.2

Superb

31 reviews

$277
Average price / night
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Wine Tastings, Hills and Tuscan home
Wine Tastings, Hills and Tuscan home
House
San Casciano in Val di Pesa, 50026, Italy
1.9k from Il Serraglio center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

6 Bedrooms9 Guests
10.0

Exceptional

6 reviews

$530
Average price / night
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La Stalla di Feo apartment with garden in the heart of Chianti for 4 people
La Stalla di Feo apartment with garden in the heart of Chianti for 4 people
House
Montespertoli, 50025, Italy
2.1k from Il Serraglio center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Living Area, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

12 reviews

$201
Average price / night
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Holiday Home 'Sweet Vallet' with Shared Pool, Private Terrace and Wi-Fi
Holiday Home 'Sweet Vallet' with Shared Pool, Private Terrace and Wi-Fi
House
San Casciano Val di Pesa, 50026, Italy
2.3k from Il Serraglio center

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

1 Bedroom4 Guests
New to Booking
$202
Average price / night
Check Availability
House with character in typical medieval borgo on the Chianti Classico hills
House with character in typical medieval borgo on the Chianti Classico hills
House
Montespertoli, 50025, Italy
2.4k from Il Serraglio center

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

4 Bedrooms8 Guests
9.6

Exceptional

51 reviews

$209
Average price / night
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House with garden in the hills of Chianti
House with garden in the hills of Chianti
House
Montespertoli, 50025, Italy
2.6k from Il Serraglio center

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

3 Bedrooms6 Guests
10.0

Exceptional

97 reviews

$258
Average price / night
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Apartment 'LEGNAIA' at IL BACIO Farmhouse
Apartment 'LEGNAIA' at IL BACIO Farmhouse
Apartment
Tavarnelle Val di Pesa, 50028, Italy
2.7k from Il Serraglio center

Barbecue, Crib, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Space

2 Bedrooms4 Guests
8.6

Fabulous

12 reviews

$169
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 Il Serraglio.

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Frequently Asked Questions

You can explore 578 verified family-friendly vacation rentals in Il Serraglio. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Il Serraglio 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 Il Serraglio 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 Il Serraglio 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 Il Serraglio often include amenities such as Child Friendly, Fireplace/Heating, and Balcony/Terrace. 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.