Family-Friendly Vacation Rentals in Simignano, Tuscany: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Simignano

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262 Best Family Vacation Rentals in Simignano (Starting from $100)

Agriturismo La Villa
Agriturismo La Villa
House
Pievescola, Italy
0.5k from Simignano center

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

7 Bedrooms16 Guests
9.2

Superb

11 reviews

$596
Average price / night
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Il Fienile di Simignano
Il Fienile di Simignano
Villa
Sovicille, 53018, Italy
0.1k from Simignano 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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Podere Casetta Entire Property in Exclusive Use Siena
Podere Casetta Entire Property in Exclusive Use Siena
House
Simignano, Tuscany, Italy
0.5k from Simignano center

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

8 Bedrooms22 Guests
9.5

Superb

2 reviews

$581
Average price / night
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Casa al Gianni - La Capanna
Casa al Gianni - La Capanna
Apartment
Sovicille, 53018, Italy
0.1k from Simignano 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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Brotes Appartamento Ciliegio
Brotes Appartamento Ciliegio
Apartment
Sovicille, Italy
2.2k from Simignano center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

1 Bedroom5 Guests
9.3

Superb

11 reviews

$241
Average price / night
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Casa al Gianni - Il Leccio
Casa al Gianni - Il Leccio
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

2 Bedrooms5 Guests
New to Booking
$184
Average price / night
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Brotes Appartamento Mandorlo
Brotes Appartamento Mandorlo
Apartment
Sovicille, Italy
2.2k from Simignano center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

1 Bedroom5 Guests
10.0

Exceptional

5 reviews

$247
Average price / night
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Casa al Gianni - La Quercia
Casa al Gianni - La Quercia
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
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Brotes Appartamento Castagno
Brotes Appartamento Castagno
Apartment
Sovicille, Italy
2.2k from Simignano center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

2 Bedrooms7 Guests
9.2

Superb

7 reviews

$697
Average price / night
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Casa al Gianni - Il Fico
Casa al Gianni - Il Fico
Apartment
Sovicille, 53018, Italy
0.1k from Simignano 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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Le Mascie
Le Mascie
Apartment
Sovicille, Italy
2.3k from Simignano center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Pet-friendly, Lodgings, Vacation rentals, Places to stay

17 Bedrooms34 Guests
9.2

Superb

69 reviews

$100
Average price / night
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Casa al Gianni - Olmo
Casa al Gianni - Olmo
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
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Villa Le Caggia
Villa Le Caggia
Villa
Sovicille, Italy
2.5k from Simignano center

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

7 Bedrooms17 Guests
10.0

Exceptional

9 reviews

$610
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
0.5k from Simignano 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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Agriturismo Poggio ai Legni
Agriturismo Poggio ai Legni
House
Sovicille, Italy
2.8k from Simignano center

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

9 Bedrooms28 Guests
9.4

Superb

144 reviews

$124
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
2.3k from Simignano 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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Borgo Il Poggiaccio Residenza d'Epoca
Borgo Il Poggiaccio Residenza d'Epoca
House
Sovicille, Italy
2.9k from Simignano center

Cheap, Accommodations, Pools, Parking, Country houses, Romantic, Cottages, Pet-friendly, Lodgings

18 Bedrooms33 Guests
9.1

Superb

408 reviews

$196
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
2.3k from Simignano 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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Roccia Cerbaia
Roccia Cerbaia
House
Simignano, Tuscany, Italy
3.0k from Simignano center

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

17 Bedrooms35 Guests
5.9

Review score

8 reviews

$1143
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
2.3k from Simignano 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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Cozy Apartment In Ancaiano
Cozy Apartment In Ancaiano
Apartment
Ancaiano, Italy
3.1k from Simignano center

Apartments, Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$174
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
2.3k from Simignano center

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

2 Bedrooms5 Guests
New to Booking
$287
Average price / night
Check Availability
Beautiful Apartment In Ancaiano
Beautiful Apartment In Ancaiano
Apartment
Ancaiano, Italy
3.1k from Simignano center

Apartments, Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$175
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
2.3k from Simignano 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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ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
Villa
Siena, Toscana, 53018, Italy
2.5k from Simignano center

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

7 Bedrooms15 Guests
10.0

Exceptional

120 reviews

$1439
Average price / night
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Charming House in Tuscany with Pool & Views
Charming House in Tuscany with Pool & Views
Apartment
Sovicille, 53018, Italy
2.7k from Simignano center

Crib, Heater, Internet, Kitchen, Living Area, No Smoking, Pool, Toys, TV

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$164
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 Simignano.

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Simignano Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 262 verified family-friendly vacation rentals in Simignano. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Simignano vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $100 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Simignano 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 Simignano 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 Simignano often include amenities such as Child Friendly, Fireplace/Heating, and Pet Friendly. 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.