A historic square with a prominent tower and statues.

Search Pienza Villa Rentals from CA $125

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Pienza villas

Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (68 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $217
CA $249 total
includes taxes & fees
Jul 23 - Jul 24
Il Poggio dell'Eremita
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is CA $111
CA $125 total
includes taxes & fees
Aug 1 - Aug 2
Artisti del Cavallo Tourism
Exterior

Panoramic country Villa 6/8 people in Tuscany, bbq wood-fired oven, heating, A/C

Panoramic country Villa 6/8 people in Tuscany, bbq wood-fired oven, heating, A/C
Sarteano
The price is CA $231
CA $268 total
includes taxes & fees
Aug 1 - Aug 2
Panoramic country Villa 6/8 people in Tuscany, bbq wood-fired oven, heating, A/C
Exterior

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

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is CA $323
CA $326 total
includes taxes & fees
Aug 10 - Aug 11
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Property grounds

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is CA $8,716
CA $9,519 total
includes taxes & fees
Jul 16 - Jul 17
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Exterior

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

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
Trequanda
The price is CA $417
CA $509 total
includes taxes & fees
Aug 8 - Aug 9
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
Exterior

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

Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups
Montenero
The price is CA $548
CA $1,049 total
includes taxes & fees
Jul 16 - Jul 17
Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups
Property grounds

Charming Tuscany Villa w/ Private Infinity Pool

Charming Tuscany Villa w/ Private Infinity Pool
Castel del Piano
The price is CA $607
CA $801 total
includes taxes & fees
Jul 17 - Jul 18
Charming Tuscany Villa w/ Private Infinity Pool
Pool

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is CA $8,765
CA $8,765 total
includes taxes & fees
Jul 17 - Jul 18
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Outdoor dining

Relax Home Holiday

Relax Home Holiday
Umbria
The price is CA $867
CA $991 total
includes taxes & fees
Jul 27 - Jul 28
Relax Home Holiday
Pool

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

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Torrita di Siena
The price is CA $5,246
CA $5,249 total
includes taxes & fees
Jul 20 - Jul 21
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Property grounds

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

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Porrona
The price is CA $1,041
CA $1,156 total
includes taxes & fees
Jul 17 - Jul 18
Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Property grounds

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

Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
Siena
10.0 out of 10, Exceptional, (1 review)
"Bellissime camere, dotate di ogni confort, immerse nel verde della campagna toscana. Camere spaziose, comode, luminose e attrezzate di tutto. Proprietari ospitali e gentili, sempre pronti a fornire indicazioni. Grazie di tutto , torneremo senz'altro!"
United States
Annarosa m.
The price is CA $1,110
CA $1,117 total
includes taxes & fees
Jul 18 - Jul 19
Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
Exterior

Casale Le Rondini with a swimming pool and private garden

Casale Le Rondini with a swimming pool and private garden
LUCIGNANO
Casale Le Rondini with a swimming pool and private garden
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is CA $1,175
CA $1,573 total
includes taxes & fees
Jul 19 - Jul 20
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Property grounds

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is CA $1,908
CA $2,263 total
includes taxes & fees
Jul 26 - Jul 27
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,755
CA $3,110 total
includes taxes & fees
Jul 26 - Jul 27
Villa Torre Among the Hills of Siena
Exterior

Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.
Trequanda
The price is CA $883
CA $1,472 total
includes taxes & fees
Jul 16 - Jul 17
Red Heart - relax with those you love in Tuscany.
Outdoor dining

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Murlo
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...
United States
martina p.
The price is CA $4,817
CA $5,068 total
includes taxes & fees
Aug 9 - Aug 10
Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Exterior

Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w
Trequanda
The price is CA $443
CA $540 total
includes taxes & fees
Jul 26 - Jul 27
Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pienza Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Very clean and very quiet"
Andrey 2-night trip
Posted 6 hours ago
Villa di Piazzano - Small Luxury Hotel of the World

Find out more about Pienza

Pienza Villas information

Number of reviews
75
Accommodation
1475 Villas
Lowest Price
CA $125
Highest Price
CA $9,519

Frequently asked questions

How much do villas in Pienza cost?
Rates for villas in Pienza range between CA $125 and CA $9,519 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 1475 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.

Explore a world of travel with Expedia