Pienza Villas from CA $125

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Our top choices for Pienza villas

Charming Tuscany Villa w/ Private Infinity Pool

Castel del Piano

CA $605 total

includes taxes & fees

May 31 - Jun 1

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning

Porrona

CA $746 total

includes taxes & fees

Jun 1 - Jun 2

Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi

Siena

Annarosa m.

CA $1,833 total

includes taxes & fees

Jun 4 - Jun 5

INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY

San Giovanni d'Asso

Stephan C.

CA $1,145 total

includes taxes & fees

Jun 10 - Jun 11

Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups

Montenero

CA $1,198 total

includes taxes & fees

Jun 4 - Jun 5

Il Poggio dell'Eremita

Sinalunga

Paul Q.

CA $260 total

includes taxes & fees

Jun 3 - Jun 4

WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool

CASTIGLIONE D'ORCIA (SI)

Teresa P.

CA $1,868 total

includes taxes & fees

Jun 11 - Jun 12

Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

San Quirico d'Orcia

CA $2,854 total

includes taxes & fees

Jun 10 - Jun 11

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Top Pienza Hotel Reviews

Affitacamere Maria Gabriella

10/10 Excellent

"Just excellent, everything! Guitar and his aunt were SO helpful. Great beast. WiFi was fast and climate control was quiet. Spent four peacefully days touring the country side and a family weding"

Monastero di Cortona Hotel & Spa

10/10 Excellent

"We had an amazing stay at the monastero di Cortona. The property is absolutely beautiful and impeccably maintained. The pool area is lovely and the views are unbelievable. The staff was super helpful and attentive- gave us recommendations for restaurants (and made reservations for us) and helped us with what to see/ do in Cortona and the surrounding area. The room was perfect and although we didn’t use the spa it looked really nice. I very much enjoyed the breakfast each morning as well. I would 100% stay here again and would recommend it to anyone going to Cortona."

Precise Tale Poggio Alla Sala

10/10 Excellent

"Beautiful stay for our honeymoon. This is definitely a place to go and feel at peace in the Tuscan countryside. 15 min away from some wineries and 20 min away from Montepulciano. Great balance of feeling relaxed by the spa and pool with some quick getaways. Lastly, the restaurant was beyond excellent. Expensive but well worth it."

Tenuta Santo Pietro

10/10 Excellent

"Beautiful villa! Everything was so cozy and inviting. The staff was very attentive and friendly- they went out of their way to accommodate us for breakfast since we were exhausted and slept in. Food was incredible, chef made and always served with a smile and light conversation. 100% would recommend and would love to return in the future ! Location was perfect as well and made trips to nearby towns/ sightseeing a breeze!!!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"I cant think of a more perfect place to stay. It is a beautiful property, with a long history, in one of the most beautiful regions of the world. We had one of the more "basic" rooms but it was still luxurious and comfortable. Amenities were great and the food/wine was amazing. We had some logistical problems with some of our travel plans and the staff was incredibly helpful. We are very grateful to Andrei, Kristian and Valeria especially. "

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, however I would choose to come back here.."

Find out more about Pienza

Pienza Villas information

Number of reviews	192
Accommodation	1517 Villas
Lowest Price	CA $125
Highest Price	CA $3,506

Frequently asked questions

How much do villas in Pienza cost?

Rates for villas in Pienza range between CA $125 and CA $3,506 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 1517 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.

How can I find cheap villas in Pienza?

An excellent way to track down cheap villas in Pienza is with Expedia's user-friendly filter tool. Narrow your search results by budget, star rating and amenities to find unbeatable rates in just a click or two.

What is there to do near my villa in Pienza?

Whatever you're interested in, Pienza has plenty to keep you going. Artemisia Gallery, Pienza Cathedral and Palazzo Comunale are on many visitors' sightseeing itineraries. Don't forget about Palazzo Piccolomini, Historic Centre of Pienza and Piazza Pio II either. With Expedia's hotel deals in Pienza, you can discover more neat attractions like these with the money you save.

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Search Pienza Villa Rentals from CA $125

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza villas

Charming Tuscany Villa w/ Private Infinity Pool

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning

Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi

INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY

Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups

Il Poggio dell'Eremita

WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool

Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

Relax Home Holiday

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Villa Capanna: A Window onto Tuscany

WP RELAIS BORGO VIGNALUNGA

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Villa Torre Among the Hills of Siena

Artisti del Cavallo Tourism

Casale Le Rondini with a swimming pool and private garden

Red Heart - relax with those you love in Tuscany.

Villa Falco-Cignella Resort Apartments in Tuscany

Villa Cielo- Cignella Resort Tuscany Accommodation

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Affitacamere Maria Gabriella

Find out more about Pienza

Pienza Villas information

Frequently asked questions

Explore a world of travel with Expedia