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

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  3.  Italy
  4.  Tuscany
  5.  Simignano

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67 Best Villa Rentals in Simignano (Starting from $132)

Villa Le Caggia
Villa Le Caggia
Villa
Sovicille, Italy
2.5k from Simignano center

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

7 Bedrooms17 Guests
10.0

Exceptional

9 reviews

$610
Average price / night
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Il Fienile di Simignano
Il Fienile di Simignano
Villa
Sovicille, 53018, Italy
0.1k from Simignano center

Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
New to Booking
$437
Average price / night
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The Casina
The Casina
Villa
Cetinale, Italy
3.0k from Simignano center

Pool, Parking, Air Conditioner, Balcony/Terrace, Internet

2 Bedrooms4 Guests
New to Booking
$1178
Average price / night
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True Tuscany Siena! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
True Tuscany Siena! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Villa
Sovicille Simignano, 53018, Italy
0.5k from Simignano center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

8 Bedrooms20 Guests
9.8

Exceptional

9 reviews

$1265
Average price / night
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Villa Rosa
Villa Rosa
Villa
Ancaiano, Italy
3.6k from Simignano center

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

2 Bedrooms4 Guests
New to Booking
$286
Average price / night
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ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
Villa
Siena, Toscana, 53018, Italy
2.5k from Simignano center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

7 Bedrooms15 Guests
10.0

Exceptional

120 reviews

$1439
Average price / night
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Treccianino 12
Treccianino 12
Villa
Sovicille, Italy
3.8k from Simignano center

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

6 Bedrooms12 Guests
New to Booking
$869
Average price / night
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La Dimora di Teresa
La Dimora di Teresa
Villa
Ancaiano, Italy
4.1k from Simignano center

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

4 Bedrooms10 Guests
9.5

Superb

6 reviews

$459
Average price / night
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Villino Marmoraia
Villino Marmoraia
Villa
Simignano, Tuscany, Italy
4.6k from Simignano center

Internet, Fireplace/Heating, Guest Services, Parking, Ocean View, Pool, Security/Safety

2 Bedrooms4 Guests
New to Booking
$198
Average price / night
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Siena, Florence, Chianti, Val d'orcia from Enchanting and exclusive Tuscan Villa
Siena, Florence, Chianti, Val d'orcia from Enchanting and exclusive Tuscan Villa
Villa
Toscana, 53018, Italy
2.5k from Simignano center

Dryer, Hot Tub, Internet, Laundry, No Smoking, Pool

7 Bedrooms16 Guests
New to Booking
$1439
Average price / night
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Villa Antico Podere Rota
Villa Antico Podere Rota
Villa
Sovicille, Italy
4.8k from Simignano center

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

6 Bedrooms10 Guests
8.9

Fabulous

12 reviews

$132
Average price / night
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Tuscan Villa with a Pool and Bucolic Grounds near Siena
Tuscan Villa with a Pool and Bucolic Grounds near Siena
Villa
Toscana, 53018, Italy
2.5k from Simignano center

Barbecue, Dryer, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

7 Bedrooms16 Guests
New to Booking
$1382
Average price / night
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L'Ovile 8, Emma Villas
L'Ovile 8, Emma Villas
Villa
Sovicille, Italy
5.2k from Simignano 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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Villa Ebe: An elegant and welcoming two-story villa in the characteristic style of the Tuscan countryside, with Free WI-FI.
Villa Ebe: An elegant and welcoming two-story villa in the characteristic style of the Tuscan countryside, with Free WI-FI.
Villa
Sovicille, 53018, Italy
2.5k from Simignano center

AC, Balcony, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Outdoor Space

7 Bedrooms14 Guests
New to Booking
$3219
Average price / night
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Podere Lorena
Podere Lorena
Villa
Monteriggioni, Italy
5.2k from Simignano center

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

6 Bedrooms12 Guests
9.0

Fabulous

2 reviews

$466
Average price / night
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Casa Viale dei Cipressi
Casa Viale dei Cipressi
Villa
Sovicille, Italy
5.3k from Simignano center

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

3 Bedrooms7 Guests
9.7

Exceptional

24 reviews

$163
Average price / night
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9- Villa La Quercia
9- Villa La Quercia
Villa
Casole d'Elsa, 53031, Italy
2.7k from Simignano center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$397
Average price / night
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LA CAPANNA DI FRANCA 6&2, Emma Villas
LA CAPANNA DI FRANCA 6&2, Emma Villas
Villa
Sovicille, Italy
5.3k from Simignano center

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

3 Bedrooms8 Guests
8.0

Good

1 reviews

$741
Average price / night
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Private Villa with A/C, private pool, hot tub, WIFI, TV, patio, panoramic view, close to Siena
Private Villa with A/C, private pool, hot tub, WIFI, TV, patio, panoramic view, close to Siena
Villa
Arnano, 53018, Italy
2.8k from Simignano center

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

7 Bedrooms16 Guests
9.2

Superb

9 reviews

$1577
Average price / night
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La Palazzina
La Palazzina
Villa
Siena, Italy
5.4k from Simignano 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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Historic Podere for 10 with Pool and Tennis Court close to Siena
Historic Podere for 10 with Pool and Tennis Court close to Siena
Villa
Siena, 53018, Italy
3.1k from Simignano center

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

4 Bedrooms10 Guests
New to Booking
$858
Average price / night
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Villa Rock Cerbaia
Villa Rock Cerbaia
Villa
Toscana, 53018, Italy
3.2k from Simignano center

Internet, No Smoking

6 Bedrooms20 Guests
New to Booking
$4739
Average price / night
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Treccianino 12, Sovicille, Siena and Chianti
Treccianino 12, Sovicille, Siena and Chianti
Villa
Sovicille, 53018, Italy
3.8k from Simignano center

Barbecue, Fireplace, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space, Pool

6 Bedrooms12 Guests
New to Booking
$896
Average price / night
Check Availability
La Dimora di Teresa: fairytale house in the woods, ideal for families with children.
La Dimora di Teresa: fairytale house in the woods, ideal for families with children.
Villa
Sovicille, 53018, Italy
4.2k from Simignano center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Extra Bed, Fireplace

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$441
Average price / night
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Villino Marmoraia In Casole d'elsa, Tuscany
Villino Marmoraia In Casole d'elsa, Tuscany
Villa
Casole d'Elsa, 53031, Italy
4.6k from Simignano center

AC, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Space

2 Bedrooms4 Guests
8.0

Good

11 reviews

$307
Average price / night
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Villa Antico Podere Rota (CIN IT052034C29DBJQPYG)
Villa Antico Podere Rota (CIN IT052034C29DBJQPYG)
Villa
Sovicille, 53025, Italy
4.6k from Simignano center

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

6 Bedrooms10 Guests
9.6

Exceptional

37 reviews

$380
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 Simignano.

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Simignano Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 67 verified villa rentals in Simignano. 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 Simignano vary depending on the season, location, and amenities. Rates typically start from around $132 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 Simignano 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 Simignano.

Yes, Simignano offers a wide range of villas ideal for group stays. Many properties include 6 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 Simignano 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 Simignano often include highly sought-after amenities such as Pool, Child Friendly, and Fireplace/Heating. These features enhance comfort and convenience, making them especially popular among travelers visiting Simignano.

To discover top-rated villas in Simignano, 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.