Vacation Rentals in San Leonardo al Lago, Monteriggioni: Compare 10+ Sites & Save

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  3.  Italy
  4.  Tuscany
  5.  Monteriggioni
  6.  San Leonardo al Lago

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1372 Best Vacation Rentals in San Leonardo al Lago (Starting from $50)

Agriturismo Tre Madonne
Agriturismo Tre Madonne
House
San Leonardo al Lago, Monteriggioni, Tuscany, Italy
0.7k from San Leonardo al Lago center

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

6 Bedrooms14 Guests
8.9

Fabulous

45 reviews

$83
Average price / night
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Nice apartment in villa for 2 people with pool, WIFI, terrace, pets allowed and panoramic view
Nice apartment in villa for 2 people with pool, WIFI, terrace, pets allowed and panoramic view
House
Arnano, 53100, Italy
0.8k from San Leonardo al Lago center

Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

1 Bedroom2 Guests
New to Booking
$211
Average price / night
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Borgo dei Fondi
Borgo dei Fondi
House
Siena, Italy
1.2k from San Leonardo al Lago center

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

5 Bedrooms13 Guests
9.6

Exceptional

114 reviews

$111
Average price / night
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Podere La Miniera Relax-Food, room with garden view
Podere La Miniera Relax-Food, room with garden view
Apartment
Siena, 53100, Italy
1.1k from San Leonardo al Lago center

Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$112
Average price / night
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Holiday Home Triangolo by Interhome
Holiday Home Triangolo by Interhome
House
Siena, Italy
1.2k from San Leonardo al Lago center

Pet Friendly, Guest Services, Security/Safety, Internet, Laundry, View, Parking

1 Bedroom2 Guests
9.3

Superb

3 reviews

$67
Average price / night
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Holiday Home Il Nespolo by Interhome
Holiday Home Il Nespolo by Interhome
House
Siena, Italy
1.2k from San Leonardo al Lago center

Pet Friendly, Guest Services, Security/Safety, Internet, Laundry, View, Parking

1 Bedroom2 Guests
8.0

Good

2 reviews

$81
Average price / night
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Il Nespolo by Interhome
Il Nespolo by Interhome
House
Siena, 53100, Italy
1.2k from San Leonardo al Lago center

Fireplace, Free Parking, Heater, Kitchen, Laundry, No Smoking, Outdoor Space, Pool, Washer

1 Bedroom2 Guests
9.6

Exceptional

10 reviews

$181
Average price / night
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Holiday Home Il Boschetto by Interhome
Holiday Home Il Boschetto by Interhome
House
Valli, Italy
1.2k from San Leonardo al Lago center

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

2 Bedrooms5 Guests
9.5

Superb

2 reviews

$290
Average price / night
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Triangolo by Interhome
Triangolo by Interhome
House
Siena, 53100, Italy
1.2k from San Leonardo al Lago center

Free Parking, Heater, Kitchen, Laundry, No Smoking, Outdoor Space, Pool, Washer

1 Bedroom2 Guests
New to Booking
$123
Average price / night
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la Senesina
la Senesina
House
Monteriggioni, Italy
1.3k from San Leonardo al Lago center

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

2 Bedrooms5 Guests
9.5

Superb

52 reviews

$50
Average price / night
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La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Apartment
Siena, 53035, Italy
1.2k from San Leonardo al Lago center

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

2 Bedrooms5 Guests
10.0

Exceptional

66 reviews

$175
Average price / night
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Agriturismo Casalino18
Agriturismo Casalino18
House
Tognazza, Italy
1.4k from San Leonardo al Lago center

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

11 Bedrooms24 Guests
9.4

Superb

270 reviews

$247
Average price / night
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\"Borgo dei Fondi\" Splendid Farmhouse free wifi-free parking
\"Borgo dei Fondi\" Splendid Farmhouse free wifi-free parking
Villa
siena, 53100, Italy
1.2k from San Leonardo al Lago center

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

5 Bedrooms13 Guests
10.0

Exceptional

11 reviews

$601
Average price / night
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La Locaia
La Locaia
Apartment
Siena, Italy
1.8k from San Leonardo al Lago center

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

2 Bedrooms4 Guests
9.7

Exceptional

21 reviews

$136
Average price / night
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Borgo dei Fondi – Tuscan Oasis with Pool, Just Minutes from Siena
Borgo dei Fondi – Tuscan Oasis with Pool, Just Minutes from Siena
House
Siena, 53100, Italy
1.2k from San Leonardo al Lago center

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

2 Bedrooms5 Guests
9.8

Exceptional

43 reviews

$203
Average price / night
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San Fedele Alloggi
San Fedele Alloggi
Apartment
Siena, Italy
2.0k from San Leonardo al Lago center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Accessible hotels

4 Bedrooms11 Guests
9.7

Exceptional

72 reviews

$467
Average price / night
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La Palazzina
La Palazzina
Villa
Siena, Italy
2.1k from San Leonardo al Lago center

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

3 Bedrooms8 Guests
9.6

Exceptional

15 reviews

$141
Average price / night
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Borgo dei Fondi / Il Forno – Ground Floor/  Modern Comfort and Tuscan Charm
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
House
siena, 53100, Italy
1.2k from San Leonardo al Lago center

AC, Barbecue, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

20 reviews

$201
Average price / night
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L'Ovile 8, Emma Villas
L'Ovile 8, Emma Villas
Villa
Sovicille, Italy
2.1k from San Leonardo al Lago center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$995
Average price / night
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Farmhouse with pool - Il Forno free wifi-free parking
Farmhouse with pool - Il Forno free wifi-free parking
House
siena, 53100, Italy
1.2k from San Leonardo al Lago center

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

4 Bedrooms8 Guests
New to Booking
$393
Average price / night
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AgritourismoAzienda Villa Cennina
AgritourismoAzienda Villa Cennina
House
Ancaiano, Italy
2.2k from San Leonardo al Lago center

Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms3 Guests
10.0

Exceptional

1 reviews

$260
Average price / night
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Cozy cottage with pool 10 km from Siena, pets allowed
Cozy cottage with pool 10 km from Siena, pets allowed
House
Siena, 53100, Italy
1.4k from San Leonardo al Lago center

AC, Barbecue, Fireplace, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$449
Average price / night
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GuestHost - Casa di Guido - Country Chic with View
GuestHost - Casa di Guido - Country Chic with View
Apartment
Fungaia, Italy
2.3k from San Leonardo al Lago center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$148
Average price / night
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Podere La Miniera Relax & Food with Shared Garden and Wi-Fi
Podere La Miniera Relax & Food with Shared Garden and Wi-Fi
Apartment
Siena, 53100, Italy
1.4k from San Leonardo al Lago center

Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$114
Average price / night
Check Availability
Beautiful apartment in villa with A/C, pool, WIFI, terrace, pets allowed and panoramic view
Beautiful apartment in villa with A/C, pool, WIFI, terrace, pets allowed and panoramic view
House
Sovicille, 53100, Italy
1.4k from San Leonardo al Lago center

AC, Barbecue, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$407
Average price / night
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Podere La Miniera: a room surrounded by greenery near Siena
Podere La Miniera: a room surrounded by greenery near Siena
Apartment
Siena, 53100, Italy
1.9k from San Leonardo al Lago center

Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$112
Average price / night
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Beautiful apartment for 4 people with WIFI, pool, TV and veranda, close to Siena
Beautiful apartment for 4 people with WIFI, pool, TV and veranda, close to Siena
Apartment
Monteriggioni, 53035, Italy
2.0k from San Leonardo al Lago center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$184
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 San Leonardo al Lago.

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Frequently Asked Questions

You can explore 1372 verified vacation rentals in San Leonardo al Lago. 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 San Leonardo al Lago vary depending on the season, property size, and location. Rates typically start from around $50 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 San Leonardo al Lago 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 San Leonardo al Lago welcome pets. Currently, 56 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 San Leonardo al Lago often include amenities such as Fireplace/Heating, Child 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.