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

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334 Best Vacation Rentals in Villa Montesoli (Starting from $80)

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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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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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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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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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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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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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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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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Villa sleeps 10 with private garden and pool.
Villa sleeps 10 with private garden and pool.
Villa
Buonconvento, 53022, Italy
1.8k from Villa Montesoli center

AC, Barbecue, Fireplace, Free Parking, Internet, Kitchen, Laundry, Microwave, Outdoor Space

5 Bedrooms10 Guests
8.0

Good

1 reviews

$916
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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Agriturismo Etrusco
Agriturismo Etrusco
House
Murlo, Italy
2.0k from Villa Montesoli center

Guest Services, Transportation/Shuttle, View, Security/Safety, Breakfast, Parking, Pool

3 Bedrooms6 Guests
9.6

Exceptional

44 reviews

$80
Average price / night
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Val D'Orcia, near Siena and Montalcino: villa, panorama and pool
Val D'Orcia, near Siena and Montalcino: villa, panorama and pool
Villa
Buonconvento, 53022, Italy
1.9k from Villa Montesoli center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$740
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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Cortile del Pozzo family home sleeps 8 with private garden by Italian Apartments
Cortile del Pozzo family home sleeps 8 with private garden by Italian Apartments
House
Buonconvento ,Siena, 53022, Italy
2.0k from Villa Montesoli center

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

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$734
Average price / night
Check Availability
BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Villa
Montalcino, 53022, Italy
2.0k from Villa Montesoli center

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

9 Bedrooms20 Guests
New to Booking
$2104
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
Check Availability
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

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 Villa Montesoli.

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Frequently Asked Questions

You can explore 334 verified vacation rentals in Villa Montesoli. 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 Villa Montesoli vary depending on the season, property size, and location. Rates typically start from around $80 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 Villa Montesoli 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 Villa Montesoli welcome pets. Currently, 57 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 Villa Montesoli often include amenities such as Pool, Child Friendly, and Fireplace/Heating. 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.