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

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160 Best Villa Rentals in Montespertoli (Starting from $93)

Villa Caterina 2 by Falcony apartments
Villa Caterina 2 by Falcony apartments
Villa
Montespertoli, Italy
2.1k from Montespertoli center

Ocean View, Oceanfront, Pool, Guest Services, Air Conditioner, Security/Safety, Pet Friendly

1 Bedroom6 Guests
New to Booking
$231
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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Villa Milani - Tenuta la Gigliola
Villa Milani - Tenuta la Gigliola
Villa
Montespertoli, Italy
2.2k from Montespertoli center

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

7 Bedrooms17 Guests
9.5

Superb

4 reviews

$870
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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Agriturismo Casale Ugolini
Agriturismo Casale Ugolini
Villa
Montespertoli, Italy
2.7k from Montespertoli center

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

5 Bedrooms12 Guests
9.5

Superb

11 reviews

$760
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
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Villa Lola by VacaVilla
Villa Lola by VacaVilla
Villa
Nebbiano, Italy
2.8k from Montespertoli center

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

6 Bedrooms12 Guests
New to Booking
$572
Average price / night
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Elegant 7 bedrooms villa in Tuscany
Elegant 7 bedrooms villa in Tuscany
Villa
Toscana, 50025, Italy
2.2k from Montespertoli center

Arcade, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, Pool

7 Bedrooms16 Guests
New to Booking
$1018
Average price / night
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Montegufoni by PosarelliVillas
Montegufoni by PosarelliVillas
Villa
Montagnana Val di Pesa, Italy
3.1k from Montespertoli center

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

17 Bedrooms52 Guests
7.2

Good

16 reviews

$150
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
2.3k from Montespertoli 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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Villa Rinaldi
Villa Rinaldi
Villa
Montespertoli, Italy
4.7k from Montespertoli center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms8 Guests
9.3

Superb

3 reviews

$502
Average price / night
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ANCIENT AIR-CND PRIVATE VILLA POOL & JACUZZI ON  FLORENCE HILLS FAMILY FRIENDLY
ANCIENT AIR-CND PRIVATE VILLA POOL & JACUZZI ON FLORENCE HILLS FAMILY FRIENDLY
Villa
Montespertoli, 50025, Italy
2.5k from Montespertoli center

Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
9.6

Exceptional

13 reviews

$500
Average price / night
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Villa Albertina
Villa Albertina
Villa
Montespertoli, Italy
5.0k from Montespertoli center

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

5 Bedrooms14 Guests
New to Booking
$1030
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
2.6k from Montespertoli 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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Casa del Sole
Casa del Sole
Villa
Montespertoli, Italy
5.9k from Montespertoli center

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

3 Bedrooms7 Guests
8.6

Fabulous

13 reviews

$93
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
2.7k from Montespertoli 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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San Martino
San Martino
Villa
Certaldo, Italy
5.9k from Montespertoli center

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

4 Bedrooms6 Guests
New to Booking
$475
Average price / night
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Villa Lola In Montespertoli, Tuscany
Villa Lola In Montespertoli, Tuscany
Villa
Montespertoli, 50025, Italy
2.8k from Montespertoli center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

6 Bedrooms12 Guests
9.0

Fabulous

2 reviews

$696
Average price / night
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VILLA TOSCANA - PISCINA PRIVATA E JACUZZI -CERTALDO
VILLA TOSCANA - PISCINA PRIVATA E JACUZZI -CERTALDO
Villa
Tresanti, Italy
6.0k from Montespertoli center

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

5 Bedrooms10 Guests
New to Booking
$617
Average price / night
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Villa La Torre 16, Montespertoli, Florence and Chianti
Villa La Torre 16, Montespertoli, Florence and Chianti
Villa
Montespertoli, 50025, Italy
2.8k from Montespertoli center

Barbecue, Dryer, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

8 Bedrooms16 Guests
New to Booking
$980
Average price / night
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VILLA FIORENZA - Five Bedroom Villa, Sleeps 10
VILLA FIORENZA - Five Bedroom Villa, Sleeps 10
Villa
Montespertoli, 50025, Italy
3.0k from Montespertoli center

AC, Free Parking, Laundry, No Smoking, Pool, Washer

5 Bedrooms10 Guests
New to Booking
$2795
Average price / night
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Holidays in the heart of Toscany
Holidays in the heart of Toscany
Villa
Montespertoli, 50025, Italy
3.1k from Montespertoli center

Barbecue, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$289
Average price / night
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Villa between Florence  Siena and Pisa. 1 km to village.  A/C in all rooms-Wi Fi
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Villa
Montespertoli, 50025, Italy
3.3k from Montespertoli center

AC, Barbecue, Breakfast Available, Crib, Free Parking, Heater, Internet, Kitchen, Laundry

10 Bedrooms21 Guests
9.4

Superb

66 reviews

$829
Average price / night
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Bright villa between Florence (20 km), Siena (50) -1 km from the village Air conditioning
Bright villa between Florence (20 km), Siena (50) -1 km from the village Air conditioning
Villa
Montespertoli, 50025, Italy
3.3k from Montespertoli center

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

10 Bedrooms21 Guests
10.0

Exceptional

1 reviews

$829
Average price / night
Check Availability
Villa in Chianti with private pool, walking to a restaurant Electric car charger
Villa in Chianti with private pool, walking to a restaurant Electric car charger
Villa
Ortimino, 50025, Italy
4.0k from Montespertoli center

AC, Balcony, Barbecue, Crib, Fireplace, Free Parking, Heater, Hot Tub, Internet

7 Bedrooms14 Guests
10.0

Exceptional

18 reviews

$737
Average price / night
Check Availability
13th Century Medieval Villa apt. 2p 1 bedroom, 45mt2 top Chianti hills Florence
13th Century Medieval Villa apt. 2p 1 bedroom, 45mt2 top Chianti hills Florence
Villa
Montespertoli, 50025, Italy
4.1k from Montespertoli center

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

1 Bedroom2 Guests
New to Booking
$204
Average price / night
Check Availability
Luxury villa Bargino
Luxury villa Bargino
Villa
Montespertoli/ firenze, 50025, Italy
4.3k from Montespertoli center

AC, Balcony, Breakfast Available, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1468
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 Villa Rentals in Montespertoli.

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Frequently Asked Questions

You can currently explore 160 verified villa rentals in Montespertoli. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Montespertoli vary depending on the season, location, and amenities. Rates typically start from around $93 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Montespertoli are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Montespertoli.

Yes, Montespertoli offers a wide range of villas ideal for group stays. Many properties include 9 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Montespertoli villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Montespertoli often include highly sought-after amenities such as Fireplace/Heating, Pool, and Internet. These features enhance comfort and convenience, making them especially popular among travelers visiting Montespertoli.

To discover top-rated villas in Montespertoli, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.