Vacation Rentals in Montespertoli, Tuscany: Compare 10+ Sites & Save

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  5.  Montespertoli

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640 Best Vacation Rentals in Montespertoli (Starting from $24)

Appartamento Old England in Chianti
Appartamento Old England in Chianti
Apartment
Montespertoli, Italy
0.4k from Montespertoli 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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Cozy and bright apartment
Cozy and bright apartment
Apartment
Montespertoli, 50025, Italy
0.3k from Montespertoli center

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

1 Bedroom3 Guests
New to Booking
$224
Average price / night
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Chianti Wine Site Apt Private Balcony - Happy Rentals
Chianti Wine Site Apt Private Balcony - Happy Rentals
Apartment
Montespertoli, Italy
0.5k from Montespertoli center

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

1 Bedroom3 Guests
9.0

Fabulous

1 reviews

$107
Average price / night
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GinCat Apartment: Fireplace, BBQ and Terrace in the Heart of Chianti
GinCat Apartment: Fireplace, BBQ and Terrace in the Heart of Chianti
Apartment
Montespertoli, 50025, Italy
0.4k from Montespertoli center

AC, Barbecue, Fireplace, Heater, Internet, Kitchen, Microwave, Patio, TV

3 Bedrooms6 Guests
New to Booking
$152
Average price / night
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La casa di Nina
La casa di Nina
Apartment
Montespertoli, Italy
0.6k from Montespertoli 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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Chianti Wine Site Apt Private Balcony, Montespertoli, Italy
Chianti Wine Site Apt Private Balcony, Montespertoli, Italy
Apartment
Montespertoli, 50025, Italy
0.5k from Montespertoli center

Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$105
Average price / night
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Cirillino Apartament
Cirillino Apartament
Apartment
Montespertoli, Italy
0.6k from Montespertoli 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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Newly renovated apartment in the heart of Chianti and Tuscany
Newly renovated apartment in the heart of Chianti and Tuscany
Apartment
Montespertoli, 50025, Italy
0.8k from Montespertoli center

AC, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$114
Average price / night
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I tre olivi
I tre olivi
Apartment
Montespertoli, Italy
0.6k from Montespertoli 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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Tuscan House Relax in the heart of the Tuscan countryside
Tuscan House Relax in the heart of the Tuscan countryside
House
Montespertoli, 50025, Italy
0.9k from Montespertoli center

Balcony, Free Parking, Heater, Internet, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$127
Average price / night
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Casa Toscana
Casa Toscana
House
Montespertoli, Italy
0.7k from Montespertoli 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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Locanda del podestà: 17th century mansion in Chianti
Locanda del podestà: 17th century mansion in Chianti
Villa
Montespertoli, 50025, Italy
0.9k from Montespertoli center

Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Outdoor Space

5 Bedrooms12 Guests
9.8

Exceptional

60 reviews

$262
Average price / night
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Appartamento I Pini
Appartamento I Pini
Apartment
Montespertoli, Italy
0.8k from Montespertoli 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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Le Rose Apartment in Tuscany
Le Rose Apartment in Tuscany
Apartment
Montespertoli, 50025, Italy
1.1k from Montespertoli center

AC, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms9 Guests
New to Booking
$328
Average price / night
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La casetta di Stefy
La casetta di Stefy
Apartment
Montespertoli, Italy
0.9k from Montespertoli 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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In the heart of chianti in the center of the village of montespertoli, nice apartment
In the heart of chianti in the center of the village of montespertoli, nice apartment
Apartment
Montespertoli, 50025, Italy
1.1k from Montespertoli center

AC, Heater, Internet, Laundry, Microwave, No Smoking, Washer

1 Bedroom2 Guests
New to Booking
$92
Average price / night
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House Ilary
House Ilary
Apartment
Montespertoli, Italy
0.9k from Montespertoli 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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Apartment with Swimming Pool and Tennis
Apartment with Swimming Pool and Tennis
Apartment
Montespertoli, 50025, Italy
1.1k from Montespertoli center

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

1 Bedroom5 Guests
10.0

Exceptional

1 reviews

$165
Average price / night
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La Medialuna
La Medialuna
Apartment
Montespertoli, Italy
0.9k from Montespertoli center

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

1 Bedroom2 Guests
9.4

Superb

11 reviews

$58
Average price / night
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Casa vacanza Annamai
Casa vacanza Annamai
House
Montespertoli, 50025, Italy
1.2k from Montespertoli center

AC, Free Parking, Heater, Kitchen, Laundry, No Smoking, Patio, Pool, TV

1 Bedroom3 Guests
8.0

Good

2 reviews

$82
Average price / night
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I Limoni Apartment in Tuscany
I Limoni Apartment in Tuscany
Apartment
Toscana, 50025, Italy
1.5k from Montespertoli center

AC, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms10 Guests
New to Booking
$318
Average price / night
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Villa Ginestruzze – Villa with Private Pool and Exclusive Suites in Tuscany
Villa Ginestruzze – Villa with Private Pool and Exclusive Suites in Tuscany
Villa
Montespertoli, 50025, Italy
1.6k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
New to Booking
$548
Average price / night
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Limonaia – Elegant Tuscan Apartment with Spacious Rooms, Pool, and Relaxation
Limonaia – Elegant Tuscan Apartment with Spacious Rooms, Pool, and Relaxation
Apartment
Montespertoli, 50025, Italy
1.8k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$255
Average price / night
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Panorama – Apartment with Terrace and Views of the Tuscan Countryside
Panorama – Apartment with Terrace and Views of the Tuscan Countryside
Apartment
Montespertoli, 50025, Italy
1.8k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

2 Bedrooms5 Guests
New to Booking
$238
Average price / night
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Casina – Tuscan Apartment with Pool among Vineyards and Olive Groves
Casina – Tuscan Apartment with Pool among Vineyards and Olive Groves
Apartment
Montespertoli, 50025, Italy
1.9k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom3 Guests
New to Booking
$149
Average price / night
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Cipressina – Spacious Tuscan Apartment with Pool for Families and Groups
Cipressina – Spacious Tuscan Apartment with Pool for Families and Groups
Apartment
Montespertoli, 50025, Italy
1.9k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

4 Bedrooms8 Guests
New to Booking
$376
Average price / night
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\"Tuscan Orchard\" Holiday House
\"Tuscan Orchard\" Holiday House
Villa
Montespertoli, 50025, Italy
1.9k from Montespertoli center

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

3 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$187
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 Vacation Rentals in Montespertoli.

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Frequently Asked Questions

You can explore 640 verified vacation rentals in Montespertoli. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Montespertoli vary depending on the season, property size, and location. Rates typically start from around $24 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Montespertoli include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Montespertoli welcome pets. Currently, 50 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Montespertoli often include amenities such as Fireplace/Heating, Pet Friendly, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.