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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 1635 Villas in Pienza with updated reviews, rates, and availability.

Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Outdoor pool, a heated pool

Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake

10.0 out of 10, Exceptional, (45)
"AGRICOLA NECI is a luxury experience all the way. From the owner Patrick to the staff (Eva, Santiago and Gregorio) everyone was there to make sure our experience was memorable. The views of the surrounding valleys are incredible. The house itself is out of a movie. I highly recommend an extended vacation here."
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Villa with pool and garden
Pool

Villa with pool and garden

Villa with pool and garden
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Outdoor pool

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

10.0 out of 10, Exceptional, (7)
"We stayed together with children and grandchildren and had a great stay. The house and grounds were beautiful and well kept and we had everything needed."
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Outdoor pool, sun loungers

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (96)
"Peaceful, quiet, tucked away beautiful in the beautiful Tuscany area. Would stay there again. Excellent property!"
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Winery Villa in the heart of Nobile Vineyards.
Interior

Winery Villa in the heart of Nobile Vineyards.

10.0 out of 10, Exceptional, (11)
"We love our stay. House and property are beautiful."
Winery Villa in the heart of Nobile Vineyards.
Beautiful private villa for 4 people with pool, A/C, WIFI, TV, terrace and parking
Pool

Beautiful private villa for 4 people with pool, A/C, WIFI, TV, terrace and parking

9.8 out of 10, Exceptional, (28)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Beautiful private villa for 4 people with pool, A/C, WIFI, TV, terrace and parking
Il Poggio dell'Eremita
Terrace/patio

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (50)
"Our family of 4 had such a beautiful time at this gorgeous villa. We only stayed for 2 nights, wish we stayed longer. Highly recommend!"
The price is SAR 555
SAR 644 total
includes taxes & fees
17 May - 18 May
Il Poggio dell'Eremita
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (78)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
Exterior

PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI

10.0 out of 10, Exceptional, (196)
"The property was beautiful and well beyond our expectations! We were a group of friends and we all are looking forward to staying again! The team at the property were amazing! "
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
Historic Villa Ferrano has modern amenities, ideal for medium-sized events.
Exterior

Historic Villa Ferrano has modern amenities, ideal for medium-sized events.

Historic Villa Ferrano has modern amenities, ideal for medium-sized events.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
A heated pool

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

10.0 out of 10, Exceptional, (48)
"we had a amazing time staying at this beautiful Villla. I highly recommend it to anyone!"
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Private Villa with A/C, WIFI, private pool, patio, panoramic view, parking, close to Montepulciano
Property grounds

Private Villa with A/C, WIFI, private pool, patio, panoramic view, parking, close to Montepulciano

8.2 out of 10, Very Good, (21)
"80 von 100 punkten. Ein sehr schönes Haus mit einem super Pool. Der Besitzer ist sehr sympathisch und hat uns frisches Gemüse gebracht, die Verwalterin ist äusserst zuvorkommend. Für den relatv hohen Preis dürfte das Mobiliar jedoch in einem besseren Zustand sein. Es hat keine bequemen Sessel im Aussenbereich um gemütlich zu sitzen, die sonnenliegen sind etwas gammlig und die Pfannen in der Küche praktisch unbrauchbar zum kochen."
Private Villa with A/C, WIFI, private pool, patio, panoramic view, parking, close to Montepulciano
Villa Ventotto by Paola Orazioli
Pool

Villa Ventotto by Paola Orazioli

9.8 out of 10, Exceptional, (17)
"We had a great time. We stayed for two days"
Villa Ventotto by Paola Orazioli
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (43)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

I Cipressi, 5 bedrooms with pool near Cortona

I Cipressi, 5 bedrooms with pool near Cortona
Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany
Terrace/patio

Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany

9.8 out of 10, Exceptional, (24)
"This property is exactly as we'd imagined it to be! Very charming, great location, beautiful views! Franco and his brother were wonderful. We would definitely stay here again!"
Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany
Villa in Siena with 4 bedrooms sleeps 8
TV

Villa in Siena with 4 bedrooms sleeps 8

10.0 out of 10, Exceptional, (42)
"We spent an unforgettable week. Beautiful nature, wonderful Siena, Florence, San Gimignano, villa Capannna di Elfo. Exceptional hosts Angelica and Claudio!"
Villa in Siena with 4 bedrooms sleeps 8
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Dining

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (10)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Villa Casale Silvia Large Private Pool, A/C, WiFi
Pool

Villa Casale Silvia Large Private Pool, A/C, WiFi

9.8 out of 10, Exceptional, (20)
"We all had a great time and would like the idea of coming back."
Villa Casale Silvia Large Private Pool, A/C, WiFi
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Pool

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

10.0 out of 10, Exceptional, (35)
"We loved this place! It feels very authentic and it’s so cozy. Would highly recommend to anyone."
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Pienza

Hotel San Gregorio
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (113)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."
The price is SAR 668
SAR 760 total
includes taxes & fees
7 May - 8 May
Hotel San Gregorio
Casanova - Panoramic Rooms and Suites
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Casanova - Panoramic Rooms and Suites

3.0 star property
9.2 out of 10, Wonderful, (47)
"Beautiful views and good breakfast "
The price is SAR 689
SAR 775 total
includes taxes & fees
25 May - 26 May
Casanova - Panoramic Rooms and Suites
Bosco della Spina
Aerial view

Bosco della Spina

9.6 out of 10, Exceptional, (151)
"Great view, indoor heated pool with a nice view, huge apartment and clean!"
The price is SAR 390
SAR 462 total
includes taxes & fees
5 May - 6 May
Bosco della Spina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Pienza cost?
Rates for villas in Pienza range between SAR 555 and SAR 555 per night. Whatever your budget, you’re sure to find a place that fits the bill with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Pienza?
Pack your suitcase and pick from 1635 villas in Pienza. For a family escape, a getaway with pals or anything in between, Expedia will help you find the right place in just a click or two.
Why book your villa in Pienza with Expedia?
With Expedia, it’s easy to find your dream villa in Pienza. Vacationing with the kids? Use our helpful filters to search for stays with amenities like WiFi and a pool. If you have a certain budget, select how much you’d like to spend and your preferred star rating. We’ll help you find the right stay in tune with your taste and style.