Family-Friendly Vacation Rentals in Piazza Machiavelli, Montespertoli: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Montespertoli
  6.  Piazza Machiavelli

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427 Best Family Vacation Rentals in Piazza Machiavelli (Starting from $24)

La casetta di Stefy
La casetta di Stefy
Apartment
Montespertoli, Italy
0.1k from Piazza Machiavelli center

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

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$76
Average price / night
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Cozy and bright apartment
Cozy and bright apartment
Apartment
Montespertoli, 50025, Italy
0.9k from Piazza Machiavelli center

Free Parking, Heater, Kitchen, Laundry, Microwave, TV, Washer

1 Bedroom3 Guests
New to Booking
$224
Average price / night
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Appartamento I Pini
Appartamento I Pini
Apartment
Montespertoli, Italy
0.1k from Piazza Machiavelli center

Parking, Guest Services, Fireplace/Heating, Security/Safety, Pet Friendly, Internet, Balcony/Terrace

1 Bedroom4 Guests
8.8

Fabulous

18 reviews

$24
Average price / night
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\"Tuscan Orchard\" Holiday House
\"Tuscan Orchard\" Holiday House
Villa
Montespertoli, 50025, Italy
1.5k from Piazza Machiavelli center

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

3 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$187
Average price / night
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House Ilary
House Ilary
Apartment
Montespertoli, Italy
0.2k from Piazza Machiavelli center

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

1 Bedroom4 Guests
9.5

Superb

2 reviews

$88
Average price / night
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Villa Latini Agriturismo La Capanna
Villa Latini Agriturismo La Capanna
House
Montespertoli, 50025, Italy
1.6k from Piazza Machiavelli center

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

4 Bedrooms7 Guests
New to Booking
$427
Average price / night
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Casa Toscana
Casa Toscana
House
Montespertoli, Italy
0.2k from Piazza Machiavelli center

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

1 Bedroom4 Guests
9.3

Superb

3 reviews

$94
Average price / night
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Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi
Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi
House
Montespertoli, 50025, Italy
1.7k from Piazza Machiavelli center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$810
Average price / night
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Appartamento La Chicchera
Appartamento La Chicchera
Apartment
Montespertoli, Italy
0.2k from Piazza Machiavelli center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom5 Guests
9.4

Superb

21 reviews

$69
Average price / night
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Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Villa
Montespertoli, 50025, Italy
1.9k from Piazza Machiavelli center

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

9 Bedrooms22 Guests
10.0

Exceptional

12 reviews

$2087
Average price / night
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La casa di Nina
La casa di Nina
Apartment
Montespertoli, Italy
0.3k from Piazza Machiavelli center

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

1 Bedroom3 Guests
9.5

Superb

24 reviews

$103
Average price / night
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Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
House
Montespertoli, 50025, Italy
1.9k from Piazza Machiavelli center

Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
4.0

Review score

1 reviews

$800
Average price / night
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Cirillino Apartament
Cirillino Apartament
Apartment
Montespertoli, Italy
0.3k from Piazza Machiavelli center

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

2 Bedrooms3 Guests
9.9

Exceptional

14 reviews

$125
Average price / night
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Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa
Montespertoli, 50025, Italy
1.9k from Piazza Machiavelli center

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

7 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$2075
Average price / night
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I tre olivi
I tre olivi
Apartment
Montespertoli, Italy
0.4k from Piazza Machiavelli center

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

1 Bedroom3 Guests
9.5

Superb

8 reviews

$92
Average price / night
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Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
Apartment
Poppiano, 50025, Italy
2.0k from Piazza Machiavelli center

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

2 Bedrooms5 Guests
8.0

Good

3 reviews

$452
Average price / night
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Casa Chiantishire
Casa Chiantishire
House
Piazza Machiavelli, Montespertoli, Tuscany, Italy
0.4k from Piazza Machiavelli center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Jacuzzis

4 Bedrooms8 Guests
9.9

Exceptional

20 reviews

$37
Average price / night
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Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Apartment
Montespertoli, 50025, Italy
2.0k from Piazza Machiavelli center

AC, Breakfast Available, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
10.0

Exceptional

22 reviews

$452
Average price / night
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Appartamento Old England in Chianti
Appartamento Old England in Chianti
Apartment
Montespertoli, Italy
0.7k from Piazza Machiavelli center

Balcony/Terrace, Air Conditioner, Internet, Breakfast, Parking, Child Friendly

3 Bedrooms6 Guests
9.2

Superb

25 reviews

$68
Average price / night
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Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Villa
Montespertoli, 50025, Italy
2.0k from Piazza Machiavelli center

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

9 Bedrooms22 Guests
10.0

Exceptional

38 reviews

$2087
Average price / night
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Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
House
Montespertoli, 50025, Italy
2.0k from Piazza Machiavelli center

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

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$727
Average price / night
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Fantastic rustic apartment with two bedrooms
Fantastic rustic apartment with two bedrooms
Apartment
Montespertoli, 50025, Italy
2.1k from Piazza Machiavelli center

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

2 Bedrooms6 Guests
New to Booking
$215
Average price / night
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Fantastic 2 Bedroom Rustic Apartment
Fantastic 2 Bedroom Rustic Apartment
Apartment
Toscana, 50025, Italy
2.1k from Piazza Machiavelli center

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

2 Bedrooms4 Guests
New to Booking
$211
Average price / night
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Amazing Rustic One Bedroom Apartment
Amazing Rustic One Bedroom Apartment
Apartment
Toscana, 50025, Italy
2.1k from Piazza Machiavelli center

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

1 Bedroom4 Guests
New to Booking
$236
Average price / night
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Amazing rustic one bedroom apartament
Amazing rustic one bedroom apartament
Apartment
Toscana, 50025, Italy
2.1k from Piazza Machiavelli center

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

1 Bedroom4 Guests
New to Booking
$236
Average price / night
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Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
House
Montespertoli, 50025, Italy
2.1k from Piazza Machiavelli center

Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
6.0

Review score

1 reviews

$623
Average price / night
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Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
House
Montespertoli, 50025, Italy
2.1k from Piazza Machiavelli center

Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
New to Booking
$378
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 Piazza Machiavelli.

Where to stay in Piazza Machiavelli? Best neighborhoods & areas

Piazza Machiavelli Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 427 verified family-friendly vacation rentals in Piazza Machiavelli. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Piazza Machiavelli vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $24 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Piazza Machiavelli 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 Piazza Machiavelli 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 Piazza Machiavelli 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.