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

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  5.  Villa Montesoli

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191 Best Family Vacation Rentals in Villa Montesoli (Starting from $114)

Historic Villa Overlooking Val D'orcia
Historic Villa Overlooking Val D'orcia
House
Buonconvento, Italy
0.2k from Villa Montesoli center

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

7 Bedrooms14 Guests
New to Booking
$1619
Average price / night
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Podere Maiano - Private Pool Villa with 9 Bdrs and Spa
Podere Maiano - Private Pool Villa with 9 Bdrs and Spa
Villa
Buonconvento, Siena, 53022, Italy
0.3k from Villa Montesoli center

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

9 Bedrooms18 Guests
9.8

Exceptional

7 reviews

$2237
Average price / night
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Podere Maiano - Private pool villa with spa
Podere Maiano - Private pool villa with spa
Villa
Buonconvento, Italy
0.4k from Villa Montesoli center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1843
Average price / night
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Luxury Ecofriendly Country Villa  - Val d'orcia
Luxury Ecofriendly Country Villa - Val d'orcia
House
Buonconvento Siena, 53022, Italy
0.4k from Villa Montesoli center

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

9 Bedrooms18 Guests
10.0

Exceptional

1 reviews

$1583
Average price / night
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Il Colle Di Donna Ilaria 16, Emma Villas
Il Colle Di Donna Ilaria 16, Emma Villas
House
Buonconvento, Italy
0.8k from Villa Montesoli center

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

8 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$1506
Average price / night
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Borgo Castelrotto - pool villa 9 bedrooms - Exclusive private wine Estate
Borgo Castelrotto - pool villa 9 bedrooms - Exclusive private wine Estate
House
Buonconvento, 53022, Italy
0.4k from Villa Montesoli center

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

9 Bedrooms20 Guests
10.0

Exceptional

7 reviews

$1846
Average price / night
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Il Fienile di Montesoli
Il Fienile di Montesoli
Villa
Villa Montesoli, Italy
1.0k from Villa Montesoli center

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

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1218
Average price / night
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Villa Anna - Nine Bedroom Villa, Sleeps 18
Villa Anna - Nine Bedroom Villa, Sleeps 18
Villa
Murlo, 53022, Italy
0.4k from Villa Montesoli center

AC, Fireplace, Free Parking, Heater, Hot Tub, Kitchen, Laundry, No Smoking, Outdoor Space

9 Bedrooms18 Guests
New to Booking
$2955
Average price / night
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Sant'Ilaria - private 2 bdrs pool villa
Sant'Ilaria - private 2 bdrs pool villa
Villa
Villa Montesoli, Italy
1.0k from Villa Montesoli center

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

2 Bedrooms4 Guests
New to Booking
$361
Average price / night
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Pool Villa with 4 Bdrs and external Sauna
Pool Villa with 4 Bdrs and external Sauna
Villa
Buonconvento, 53022, Italy
0.7k from Villa Montesoli center

AC, Balcony, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry

4 Bedrooms8 Guests
New to Booking
$1038
Average price / night
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Villa di Montesoli
Villa di Montesoli
Villa
Villa Montesoli, Italy
1.1k from Villa Montesoli center

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

1 Bedroom18 Guests
New to Booking
$2333
Average price / night
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Sant'Ilaria - Private Pool Villa with 2 Bdrs
Sant'Ilaria - Private Pool Villa with 2 Bdrs
Villa
Siena, 53022, Italy
1.0k from Villa Montesoli center

AC, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$422
Average price / night
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Cortile Del Pozzo
Cortile Del Pozzo
House
Buonconvento, Italy
1.5k from Villa Montesoli center

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

4 Bedrooms8 Guests
8.0

Good

3 reviews

$362
Average price / night
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Villa di Montesoli - Buonconvento
Villa di Montesoli - Buonconvento
Villa
Buonconvento, 53022, Italy
1.1k from Villa Montesoli center

AC, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

9 Bedrooms18 Guests
New to Booking
$2961
Average price / night
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Il Colle Verde
Il Colle Verde
House
Villa Montesoli, Italy
1.8k from Villa Montesoli center

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

3 Bedrooms17 Guests
New to Booking
$435
Average price / night
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Stunning estate + winery operating as two luxury villas + infinity pool
Stunning estate + winery operating as two luxury villas + infinity pool
House
Bibbiano, 53022, Italy
1.5k from Villa Montesoli center

AC, Breakfast Included, Extra Bed, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Living Area

16 Bedrooms38 Guests
New to Booking
$12669
Average price / night
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Bibbianello
Bibbianello
Villa
Buonconvento, Italy
1.8k from Villa Montesoli center

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

5 Bedrooms10 Guests
9.2

Superb

5 reviews

$335
Average price / night
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Villa Aiale, 7 En-Suite Bdrs, AC Throughout, Private Pool – Wine Estate
Villa Aiale, 7 En-Suite Bdrs, AC Throughout, Private Pool – Wine Estate
Villa
Buonconvento, 53022, Italy
1.9k from Villa Montesoli center

AC, Barbecue, Crib, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

7 Bedrooms14 Guests
10.0

Exceptional

5 reviews

$1665
Average price / night
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Villa Fragranza - Homelike Villas
Villa Fragranza - Homelike Villas
Villa
Buonconvento, Italy
1.8k from Villa Montesoli center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$434
Average price / night
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Apartment 'Sulle Colline Di Siena' with Shared Pool, Wi-Fi and Air Conditioning
Apartment 'Sulle Colline Di Siena' with Shared Pool, Wi-Fi and Air Conditioning
Apartment
Murlo, 53016, Italy
2.2k from Villa Montesoli center

AC, Barbecue, Free Parking, Internet, Kitchen, No Smoking, Outdoor Space, Pool

1 Bedroom3 Guests
New to Booking
$160
Average price / night
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Agriturismo La Ripolina
Agriturismo La Ripolina
House
Buonconvento, Italy
1.9k from Villa Montesoli center

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

12 Bedrooms30 Guests
8.6

Fabulous

173 reviews

$223
Average price / night
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VILLA CERRETO - Seven Bedroom Villa, Sleeps 14
VILLA CERRETO - Seven Bedroom Villa, Sleeps 14
Villa
Montalcino, 53022, Italy
2.3k from Villa Montesoli center

AC, Free Parking, Heater, Kitchen, Living Area, No Smoking, Outdoor Space, Pool, Washer

8 Bedrooms14 Guests
New to Booking
$2310
Average price / night
Check Availability
Etruscan house in magic location, with 3 double bedrooms, real Tuscan experience
Etruscan house in magic location, with 3 double bedrooms, real Tuscan experience
House
Murlo, 53016, Italy
2.4k from Villa Montesoli center

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

3 Bedrooms6 Guests
New to Booking
$591
Average price / night
Check Availability
Apartment 'Elegante Vicino Siena' with Shared Pool, Wi-Fi and Air Conditioning
Apartment 'Elegante Vicino Siena' with Shared Pool, Wi-Fi and Air Conditioning
Apartment
Murlo, 53016, Italy
2.6k from Villa Montesoli center

AC, Barbecue, Free Parking, Internet, Kitchen, No Smoking, Outdoor Space, Pool

3 Bedrooms7 Guests
New to Booking
$359
Average price / night
Check Availability
House with garden in the middle of etruscan hills
House with garden in the middle of etruscan hills
Apartment
Vescovado SI, 53016, Italy
5.2k from Villa Montesoli center

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

2 Bedrooms4 Guests
10.0

Exceptional

10 reviews

$114
Average price / night
Check Availability
Vacation home among the scent and charm of the Tuscan countryside
Vacation home among the scent and charm of the Tuscan countryside
Apartment
Vescovado di Murlo, 53016, Italy
5.2k from Villa Montesoli center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$126
Average price / night
Check Availability
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Farmhouse in the greenery of the Tuscany countryside with private pool and view
House
Murlo, 53016, Italy
5.2k from Villa Montesoli center

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

4 Bedrooms10 Guests
9.6

Exceptional

53 reviews

$327
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 Villa Montesoli.

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Villa Montesoli Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 191 verified family-friendly vacation rentals in Villa Montesoli. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Villa Montesoli vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $114 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Villa Montesoli 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 Villa Montesoli 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 Villa Montesoli often include amenities such as Child Friendly, Pool, 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.