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

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887 Best Family Vacation Rentals in Montescudaio (Starting from $59)

CASE&COLLINE La Serra Nuova
CASE&COLLINE La Serra Nuova
House
Montescudaio, Italy
0.8k from Montescudaio center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$115
Average price / night
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La Capinere 2 2
La Capinere 2 2
Apartment
Montescudaio, 56040, Italy
1.0k from Montescudaio center

AC, Barbecue, Fireplace, Heater, Laundry, Living Area, No Smoking, Washer

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$124
Average price / night
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Agriturismo Sant Elmira - Relax with external Jacuzzi
Agriturismo Sant Elmira - Relax with external Jacuzzi
House
Montescudaio, Italy
0.8k from Montescudaio center

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

6 Bedrooms12 Guests
9.3

Superb

18 reviews

$206
Average price / night
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LODGE TENT MARGHERITA 5 p.
LODGE TENT MARGHERITA 5 p.
Apartment
Montescudaio, 56040, Italy
1.1k from Montescudaio center

Barbecue, Laundry, Living Area, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$147
Average price / night
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Agriturismo Fattoria La Prugnola
Agriturismo Fattoria La Prugnola
House
Montescudaio, Italy
1.1k from Montescudaio center

Cheap, Accommodations, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

19 Bedrooms62 Guests
9.3

Superb

25 reviews

$59
Average price / night
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I Colombi 2 2
I Colombi 2 2
Apartment
Montescudaio, 56040, Italy
1.1k from Montescudaio center

AC, Balcony, Barbecue, Fireplace, Heater, Internet, Laundry, Living Area, No Smoking

1 Bedroom2 Guests
New to Booking
$127
Average price / night
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Suite San Martino - Cecina Riparbella casa vacanze
Suite San Martino - Cecina Riparbella casa vacanze
Apartment
Riparbella, Italy
1.2k from Montescudaio center

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

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$173
Average price / night
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Lodge tent Ginestra 4 p.
Lodge tent Ginestra 4 p.
Apartment
Montescudaio, 56040, Italy
1.1k from Montescudaio center

Balcony, Barbecue, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space, TV

2 Bedrooms3 Guests
New to Booking
$104
Average price / night
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La Casetta di Cate
La Casetta di Cate
Apartment
Riparbella, Italy
1.3k from Montescudaio center

Hot Tub, Pool, Fireplace/Heating, Security/Safety, Air Conditioner, Pet Friendly, Internet

2 Bedrooms5 Guests
8.5

Very Good

33 reviews

$76
Average price / night
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Le Tortore 6 2
Le Tortore 6 2
Apartment
Montescudaio, 56040, Italy
1.1k from Montescudaio center

AC, Balcony, Barbecue, Fireplace, Heater, Laundry, Living Area, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$197
Average price / night
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La casa di Arturo Pet friendly Apartments
La casa di Arturo Pet friendly Apartments
Apartment
Riparbella, Italy
1.5k from Montescudaio center

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

1 Bedroom4 Guests
1.0

Review score

1 reviews

$174
Average price / night
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I Lecci 4+2
I Lecci 4+2
Apartment
Montescudaio, 56040, Italy
1.1k from Montescudaio center

AC, Balcony, Barbecue, Fireplace, Heater, Laundry, Living Area, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$176
Average price / night
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Max and Lea's House
Max and Lea's House
Apartment
Riparbella, Italy
1.5k from Montescudaio center

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

1 Bedroom4 Guests
New to Booking
$151
Average price / night
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The Sunflowers - Sea View
The Sunflowers - Sea View
Apartment
Montescudaio, 56040, Italy
1.1k from Montescudaio center

AC, Balcony, Barbecue, Fireplace, Heater, Laundry, Living Area, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$162
Average price / night
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VILLA LIGUSTRO
VILLA LIGUSTRO
Villa
Riparbella, Italy
1.5k from Montescudaio center

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

6 Bedrooms16 Guests
8.2

Very Good

14 reviews

$238
Average price / night
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The Olive  4+2
The Olive 4+2
Apartment
Montescudaio, 56040, Italy
1.2k from Montescudaio center

AC, Barbecue, Fireplace, Heater, Laundry, Living Area, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$187
Average price / night
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Il Panorama
Il Panorama
Apartment
Montescudaio, Italy
1.5k from Montescudaio center

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

4 Bedrooms14 Guests
9.7

Exceptional

20 reviews

$416
Average price / night
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I Noci
I Noci
Apartment
Montescudaio, 56040, Italy
1.3k from Montescudaio center

AC, Balcony, Barbecue, Fireplace, Heater, Laundry, Living Area, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$174
Average price / night
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Agriturismo Le Serre
Agriturismo Le Serre
House
Riparbella, Italy
1.5k from Montescudaio center

Cheap, Accommodations, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms16 Guests
9.6

Exceptional

28 reviews

$91
Average price / night
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Nice apartment in villa for 4 guests with pool, terrace and pets allowed
Nice apartment in villa for 4 guests with pool, terrace and pets allowed
House
Valserena, 56040, Italy
1.4k from Montescudaio center

Barbecue, Crib, Free Parking, Heater, Kitchen, Laundry, No Smoking, Outdoor Space, Pool

1 Bedroom4 Guests
New to Booking
$151
Average price / night
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Agriturismo I Cerroni Montescudaio
Agriturismo I Cerroni Montescudaio
House
Montescudaio, Italy
1.5k from Montescudaio center

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

1 Bedroom2 Guests
8.8

Fabulous

19 reviews

$66
Average price / night
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Beautiful apartment in villa for 6 guests with pool, terrace and pets allowed
Beautiful apartment in villa for 6 guests with pool, terrace and pets allowed
House
Valserena, 56040, Italy
1.6k from Montescudaio center

Barbecue, Crib, Free Parking, Heater, Kids Pool, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms6 Guests
New to Booking
$196
Average price / night
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Cosy apartment in villa for 8 guests with pool, terrace and pets allowed
Cosy apartment in villa for 8 guests with pool, terrace and pets allowed
House
Guardistallo, 56040, Italy
1.6k from Montescudaio center

Barbecue, Crib, Fireplace, Free Parking, Heater, Laundry, No Smoking, Outdoor Space, Pool

3 Bedrooms8 Guests
New to Booking
$260
Average price / night
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Cosy apartment in villa for 11 guests with pool, terrace and pets allowed
Cosy apartment in villa for 11 guests with pool, terrace and pets allowed
House
Guardistallo, 56040, Italy
1.6k from Montescudaio center

Barbecue, Crib, Free Parking, Heater, Kitchen, Laundry, No Smoking, Outdoor Space, Pool

4 Bedrooms11 Guests
New to Booking
$288
Average price / night
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Rio del sole by Interhome
Rio del sole by Interhome
Apartment
Montescudaio, 56040, Italy
1.7k from Montescudaio center

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

1 Bedroom4 Guests
New to Booking
$104
Average price / night
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Il Borgo by Interhome
Il Borgo by Interhome
Apartment
Guardistallo, 56040, Italy
1.8k from Montescudaio center

Barbecue, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Pool

4 Bedrooms11 Guests
9.4

Superb

3 reviews

$248
Average price / night
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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 Montescudaio.

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Montescudaio Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 887 verified family-friendly vacation rentals in Montescudaio. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Montescudaio vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $59 per night, with larger homes and peak travel periods often costing more.

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