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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Simignano

Refine your search

Price per night

Amenity Filter

Rating

440 Best Vacation Rentals in Simignano (Starting from $100)

Agriturismo La Villa
Agriturismo La Villa
House
Pievescola, Italy
0.5k from Simignano center

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

7 Bedrooms16 Guests
9.2

Superb

11 reviews

$596
Average price / night
Check Availability
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
Check Availability
Podere Casetta Entire Property in Exclusive Use Siena
Podere Casetta Entire Property in Exclusive Use Siena
House
Simignano, Tuscany, Italy
0.5k from Simignano center

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

8 Bedrooms22 Guests
9.5

Superb

2 reviews

$581
Average price / night
Check Availability
Casa al Gianni - La Capanna
Casa al Gianni - La Capanna
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

1 Bedroom2 Guests
New to Booking
$138
Average price / night
Check Availability
Brotes Appartamento Ciliegio
Brotes Appartamento Ciliegio
Apartment
Sovicille, Italy
2.2k from Simignano center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

1 Bedroom5 Guests
9.3

Superb

11 reviews

$241
Average price / night
Check Availability
Casa al Gianni - Il Leccio
Casa al Gianni - Il Leccio
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

2 Bedrooms5 Guests
New to Booking
$184
Average price / night
Check Availability
Brotes Appartamento Mandorlo
Brotes Appartamento Mandorlo
Apartment
Sovicille, Italy
2.2k from Simignano center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

1 Bedroom5 Guests
10.0

Exceptional

5 reviews

$247
Average price / night
Check Availability
Casa al Gianni - La Quercia
Casa al Gianni - La Quercia
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
Check Availability
Brotes Appartamento Castagno
Brotes Appartamento Castagno
Apartment
Sovicille, Italy
2.2k from Simignano center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

2 Bedrooms7 Guests
9.2

Superb

7 reviews

$697
Average price / night
Check Availability
Casa al Gianni - Il Fico
Casa al Gianni - Il Fico
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

Balcony, Barbecue, Breakfast Available, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$184
Average price / night
Check Availability
Le Mascie
Le Mascie
Apartment
Sovicille, Italy
2.3k from Simignano center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Pet-friendly, Lodgings, Vacation rentals, Places to stay

17 Bedrooms34 Guests
9.2

Superb

69 reviews

$100
Average price / night
Check Availability
Casa al Gianni - Olmo
Casa al Gianni - Olmo
Apartment
Sovicille, 53018, Italy
0.1k from Simignano center

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

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
Check Availability
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
Check Availability
House with swimming pool is fenced garden
House with swimming pool is fenced garden
House
Sovicille, 53100, Italy
0.2k from Simignano center

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

2 Bedrooms4 Guests
8.8

Fabulous

19 reviews

$230
Average price / night
Check Availability
Agriturismo Poggio ai Legni
Agriturismo Poggio ai Legni
House
Sovicille, Italy
2.8k from Simignano center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals

9 Bedrooms28 Guests
9.4

Superb

144 reviews

$124
Average price / night
Check Availability
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
Check Availability
Borgo Il Poggiaccio Residenza d'Epoca
Borgo Il Poggiaccio Residenza d'Epoca
House
Sovicille, Italy
2.9k from Simignano center

Cheap, Accommodations, Pools, Parking, Country houses, Romantic, Cottages, Pet-friendly, Lodgings

18 Bedrooms33 Guests
9.1

Superb

408 reviews

$196
Average price / night
Check Availability
'Brotes Appartamento Ciliegio' Apartment with Shared Pool, Wi-Fi and Air Conditioning
'Brotes Appartamento Ciliegio' Apartment with Shared Pool, Wi-Fi and Air Conditioning
Apartment
Sovicille, 53018, Italy
1.9k from Simignano center

AC, Barbecue, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$579
Average price / night
Check Availability
Roccia Cerbaia
Roccia Cerbaia
House
Simignano, Tuscany, Italy
3.0k from Simignano center

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

17 Bedrooms35 Guests
5.9

Review score

8 reviews

$1143
Average price / night
Check Availability
'Brotes Appartamento Mandorlo' Apartment with Shared Pool, Wi-Fi, and Air Conditioning
'Brotes Appartamento Mandorlo' Apartment with Shared Pool, Wi-Fi, and Air Conditioning
Apartment
Sovicille, 53018, Italy
1.9k from Simignano center

AC, Barbecue, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$605
Average price / night
Check Availability
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
Check Availability
Apartment in Chianti with pool ID 450
Apartment in Chianti with pool ID 450
Cottage
Sovicille, 53031, Italy
2.2k from Simignano center

Balcony, Fireplace, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$319
Average price / night
Check Availability
Apartment in Chianti with pool ID 453
Apartment in Chianti with pool ID 453
Cottage
Sovicille, 53031, Italy
2.2k from Simignano center

Balcony, Fireplace, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$319
Average price / night
Check Availability
Apartment in Chianti with pool ID 455
Apartment in Chianti with pool ID 455
Cottage
Sovicille, 53031, Italy
2.2k from Simignano center

Balcony, Fireplace, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, TV

2 Bedrooms4 Guests
New to Booking
$293
Average price / night
Check Availability
Beautiful apartment in Casole d'Elsa
Beautiful apartment in Casole d'Elsa
Apartment
Casole d'Elsa, 53031, Italy
2.3k from Simignano center

Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$383
Average price / night
Check Availability
Pet friendly apartment in Casole D'Elsa with WiFi
Pet friendly apartment in Casole D'Elsa with WiFi
Apartment
Casole D'Elsa, 53031, Italy
2.3k from Simignano center

Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Pool

2 Bedrooms4 Guests
New to Booking
$291
Average price / night
Check Availability
Cozy apartment in Casole d'Elsa with WiFi
Cozy apartment in Casole d'Elsa with WiFi
Apartment
Casole d'Elsa, 53031, Italy
2.3k from Simignano center

Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Outdoor Space, Pool

1 Bedroom2 Guests
New to Booking
$198
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 Simignano.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Simignano's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Simignano Vacation Rentals on the Map

Frequently Asked Questions

You can explore 440 verified vacation rentals in Simignano. 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 Simignano vary depending on the season, property size, and location. Rates typically start from around $100 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 Simignano 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 Simignano welcome pets. Currently, 71 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 Simignano 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.