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

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883 Best Vacation Rentals in Pienza (Starting from $95)

Villa Fonte all'Oppio con area piscina recintata
Villa Fonte all'Oppio con area piscina recintata
Villa
Pienza, Tuscany, Italy
0.5k from Pienza center

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

10 Bedrooms21 Guests
8.9

Fabulous

47 reviews

$116
Average price / night
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Dimora Buonriposo Pienza Country House
Dimora Buonriposo Pienza Country House
House
Toscana, 53026, Italy
0.7k from Pienza center

Barbecue, Breakfast Included, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$3674
Average price / night
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Agriturismo Marinello
Agriturismo Marinello
House
Pienza, Italy
1.1k from Pienza center

Cheap, Accommodations, Pools, Farm stays, Parking, Romantic, Cottages, Lodgings, Vacation rentals

6 Bedrooms16 Guests
9.5

Superb

668 reviews

$222
Average price / night
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Villa Le Fontanelle by Fantasia Villas
Villa Le Fontanelle by Fantasia Villas
Villa
Tuscany, 53026, Italy
0.8k from Pienza center

AC, Barbecue, Dryer, Fireplace, Internet, Kitchen, Laundry, Living Area, Microwave

7 Bedrooms14 Guests
New to Booking
$871
Average price / night
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Agriturismo Barbi
Agriturismo Barbi
House
Monticchiello, Italy
1.3k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

8 Bedrooms28 Guests
9.1

Superb

306 reviews

$155
Average price / night
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Your piece of Heaven: Pure Relax in a charming & historical Villa
Your piece of Heaven: Pure Relax in a charming & historical Villa
Villa
PIENZA, 53026, Italy
0.9k from Pienza center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Laundry, Living Area, Outdoor Space

4 Bedrooms9 Guests
9.8

Exceptional

27 reviews

$445
Average price / night
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Agriturismo il Casato Mag-il Giogo
Agriturismo il Casato Mag-il Giogo
House
Pienza, Italy
1.4k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Places to stay, Accessible hotels

2 Bedrooms9 Guests
9.4

Superb

20 reviews

$392
Average price / night
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L'Olmo
L'Olmo
House
SP 88 Orcia delle Macchie, Pienza, 53026, Italy
1.1k from Pienza center

AC, Bar, Breakfast Included, Free Parking, Housekeeping, Internet, Laundry, Outdoor Space, Pool

10.0

Exceptional

22 reviews

$510
Average price / night
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Podere Casa Rossa a Pienza
Podere Casa Rossa a Pienza
Apartment
Pienza, Italy
1.5k from Pienza center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Jacuzzis, Places to stay, Family

4 Bedrooms8 Guests
9.9

Exceptional

7 reviews

$283
Average price / night
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Pienza villa rental with pool
Pienza villa rental with pool
Villa
Monticchiello, 53026, Italy
1.1k from Pienza center

AC, Balcony, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen

7 Bedrooms14 Guests
New to Booking
$1064
Average price / night
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Agriturismo il Casato Mag-il Vaglio
Agriturismo il Casato Mag-il Vaglio
House
Pienza, Italy
1.5k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Places to stay, Accessible hotels

2 Bedrooms5 Guests
8.9

Fabulous

21 reviews

$245
Average price / night
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My Rental Homes - Villa Monticchiello with pool and garden surrounding the property
My Rental Homes - Villa Monticchiello with pool and garden surrounding the property
Villa
Pienza, 53026, Italy
1.2k from Pienza center

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

7 Bedrooms14 Guests
New to Booking
$1311
Average price / night
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Agriturismo il Casato - il Torchio
Agriturismo il Casato - il Torchio
House
Pienza, Italy
1.5k from Pienza center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Places to stay, Accessible hotels

1 Bedroom5 Guests
9.4

Superb

31 reviews

$222
Average price / night
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Villa for 14 People with private pool
Villa for 14 People with private pool
Villa
Monticchiello, 53026, Italy
1.2k from Pienza center

AC, Barbecue, Breakfast Available, Crib, Fireplace, Free Parking, Heater, Hot Tub, Internet

7 Bedrooms14 Guests
New to Booking
$1036
Average price / night
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Suite Gioconda a Pienza
Suite Gioconda a Pienza
House
Pienza, Italy
1.5k from Pienza center

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

2 Bedrooms4 Guests
9.4

Superb

17 reviews

$320
Average price / night
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Splendid farmhouse in the heart of the Val d'Orcia
Splendid farmhouse in the heart of the Val d'Orcia
Villa
Pienza, 53026, Italy
1.2k from Pienza center

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

7 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$889
Average price / night
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Agriturismo Santa Maria
Agriturismo Santa Maria
House
Pienza, Italy
1.6k from Pienza center

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

7 Bedrooms13 Guests
9.8

Exceptional

68 reviews

$99
Average price / night
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Villa in Monticchiello with pool,Airconditioning,BBQ,Garten,Table tennis,sleep14
Villa in Monticchiello with pool,Airconditioning,BBQ,Garten,Table tennis,sleep14
House
Monticchiello, 53026, Italy
1.3k from Pienza center

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

7 Bedrooms14 Guests
New to Booking
$823
Average price / night
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Agriturismo Casalpiano
Agriturismo Casalpiano
House
Pienza, Italy
1.6k from Pienza center

Cheap, Accommodations, Pools, Farm stays, Parking, Romantic, Cottages, Lodgings, Vacation rentals

6 Bedrooms12 Guests
9.5

Superb

161 reviews

$95
Average price / night
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Il Podere di Casa Rossa Pienza
Il Podere di Casa Rossa Pienza
Apartment
Pienza, 53026, Italy
1.5k from Pienza center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$293
Average price / night
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Agriturismo Podere Chiassaie
Agriturismo Podere Chiassaie
House
Monticchiello, Italy
1.7k from Pienza center

View, Parking, Fireplace/Heating, Child Friendly

3 Bedrooms8 Guests
9.1

Superb

19 reviews

$130
Average price / night
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Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Apartment
Pienza, 53026, Italy
1.5k from Pienza center

Heater, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom4 Guests
New to Booking
$329
Average price / night
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Dolce Pienza - Modern Home in the Historic Center
Dolce Pienza - Modern Home in the Historic Center
House
Tuscany, 53026, Italy
1.6k from Pienza center

AC, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom5 Guests
New to Booking
$345
Average price / night
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1 Bedroom Private vacation home in Castiglione d'Orcia
1 Bedroom Private vacation home in Castiglione d'Orcia
House
Castiglione d'Orcia, 53026, Italy
1.6k from Pienza center

Free Parking, No Smoking

1 Bedroom2 Guests
New to Booking
$276
Average price / night
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Villa Rango - Private villa with swimming pool
Villa Rango - Private villa with swimming pool
Villa
Pienza, 53026, Italy
1.7k from Pienza center

AC, Barbecue, Extra Bed, Fireplace, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

6 Bedrooms13 Guests
New to Booking
$1093
Average price / night
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Private Villa with A/C, private pool, internet, TV, patio, panoramic view, close to Montepulciano
Private Villa with A/C, private pool, internet, TV, patio, panoramic view, close to Montepulciano
Villa
Monticchiello, 53026, Italy
1.7k from Pienza center

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

7 Bedrooms14 Guests
New to Booking
$1172
Average price / night
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Beautiful villa with swimming pool in Val d'Orcia
Beautiful villa with swimming pool in Val d'Orcia
Villa
Pienza, 53026, Italy
1.7k from Pienza center

Barbecue, Extra Bed, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

6 Bedrooms12 Guests
New to Booking
$2099
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 Pienza.

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Frequently Asked Questions

You can explore 883 verified vacation rentals in Pienza. 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 Pienza vary depending on the season, property size, and location. Rates typically start from around $95 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 Pienza 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 Pienza welcome pets. Currently, 35 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 Pienza often include amenities such as Fireplace/Heating, Internet, and Balcony/Terrace. 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.