Villas in Pienza

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Pienza villas

An outdoor dining area with a table set for two, a large umbrella, and a view of a historic building in the background.

1. VILLA IL POGGIO - Four Bedroom Villa, Sleeps 8

VILLA IL POGGIO - Four Bedroom Villa, Sleeps 8
Montalcino
$4,071 nightly
The price is $4,071
Nov 15 - Nov 16
Total with taxes and fees
VILLA IL POGGIO - Four Bedroom Villa, Sleeps 8
A two-story building with balconies, outdoor seating, and potted plants.

2. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
$75 nightly
The price is $87
Nov 18 - Nov 19
Total with taxes and fees
Artisti del Cavallo Tourism
A swimming pool with lounge chairs, a stone building, and a forested hillside.

3. WPRELAIS BORGO VIGNALUNGA

WPRELAIS BORGO VIGNALUNGA
Toscana
10.0 out of 10, Exceptional, (39 reviews)
"This villa is amazing! The views are spectacular. The home is awesome! The property is beautiful! "
United States
Jeremy F.
$1,079 nightly
The price is $1,083
Nov 22 - Nov 23
Total with taxes and fees
WPRELAIS BORGO VIGNALUNGA
A stone pool with lounge chairs, a pergola, and a rustic building in the background.

4. Wp Relais Villa Vignalunga

Wp Relais Villa Vignalunga
CASTIGLIONE D'ORCIA (SI)
10.0 out of 10, Exceptional, (58 reviews)
"Amazing place to stay!! Absolutely beautiful home with unbeatable views of the countryside. The pool was wonderful to come home to after exploring. The host was also super responsive and helped us set up an amazing cooking class/dinner which far far exceeded our expectations. I wouldn’t stay anywhere else if I ever come back to Tuscany!!"
United States
Samantha L.
$831 nightly
The price is $836
Nov 18 - Nov 19
Total with taxes and fees
Wp Relais Villa Vignalunga
A swimming pool with a curved edge, surrounded by a paved deck and a wooden fence.

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

Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
San Quirico d'Orcia
$2,027 nightly
The price is $2,032
Nov 30 - Dec 1
Total with taxes and fees
Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
An aerial view of a property with a swimming pool, multiple small buildings, and a winding road.

6. 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
$212 nightly
The price is $259
Nov 18 - Nov 19
Total with taxes and fees
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
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

7. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
$183 nightly
The price is $185
Nov 17 - Nov 18
Total with taxes and fees
Il Poggio dell'Eremita
A patio with outdoor furniture, a brick wall, and a view of the sea.

8. Villa Falco-Cignella Resort Apartments in Tuscany

Villa Falco-Cignella Resort Apartments in Tuscany
Trequanda
$313 nightly
The price is $316
Nov 15 - Nov 16
Total with taxes and fees
Villa Falco-Cignella Resort Apartments in Tuscany
A tree, a lamp post, and a clear blue pool with a view of distant mountains.

9. 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
10.0 out of 10, Exceptional, (1 review)
"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."
United States
Nate D.
$2,125 nightly
The price is $2,127
Nov 15 - Nov 16
Total with taxes and fees
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
A patio with a table and chairs, a large umbrella, and a vase of flowers.

10. Villa Cielo- Cignella Resort Tuscany Accommodation

Villa Cielo- Cignella Resort Tuscany Accommodation
Trequanda
$316 nightly
The price is $319
Nov 15 - Nov 16
Total with taxes and fees
Villa Cielo- Cignella Resort Tuscany Accommodation
A large, red-roofed villa surrounded by lush green fields and rolling hills.

11. '...a delicious farmhouse in the countryside where only the wind blows...'

'...a delicious farmhouse in the countryside where only the wind blows...'
Campiglia d'Orcia
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...
United States
Li-Shen L.
$1,513 nightly
The price is $1,518
Nov 17 - Nov 18
Total with taxes and fees
'...a delicious farmhouse in the countryside where only the wind blows...'
A stone building with a garden pathway leading to it.

12. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
$7,055 nightly
The price is $7,055
Nov 15 - Nov 16
Total with taxes and fees
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

13. Red Heart - Relax with Your Loved Ones in Tuscany

Red Heart - Relax with Your Loved Ones in Tuscany
Trequanda
$888 nightly
The price is $892
Nov 15 - Nov 16
Total with taxes and fees
Red Heart - Relax with Your Loved Ones in Tuscany
A building with a red facade, green shutters, and a tiled roof.

14. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
Trequanda
$615 nightly
The price is $618
Nov 15 - Nov 16
Total with taxes and fees
Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
A Mediterranean-style villa with arched windows, a tiled roof, and a well-maintained garden with various shrubs and flowers.

15. Villa Aquila-Cignella Resort Acommodation Tuscany

Villa Aquila-Cignella Resort Acommodation Tuscany
Trequanda
$526 nightly
The price is $530
Nov 15 - Nov 16
Total with taxes and fees
Villa Aquila-Cignella Resort Acommodation Tuscany
A house with a patio area featuring outdoor furniture, a brick wall, and a view of the sea.

16. Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi

Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
$595 nightly
The price is $599
Nov 15 - Nov 16
Total with taxes and fees
Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
A building with a red facade, green shutters, and a tiled roof.

17. Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi

Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
$615 nightly
The price is $618
Nov 15 - Nov 16
Total with taxes and fees
Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi
A courtyard with a pathway, a small pool, and a variety of trees and shrubs.

18. 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
$212 nightly
The price is $259
Nov 22 - Nov 23
Total with taxes and fees
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
An aerial view of a property with a swimming pool, multiple small buildings, and a winding road.

19. 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
$221 nightly
The price is $270
Nov 18 - Nov 19
Total with taxes and fees
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
A hot tub in a grassy area with a row of tall trees in the background.

20. Godiluva, Weinvilla

Godiluva, Weinvilla
Toscana
$3,948 nightly
The price is $3,953
Nov 16 - Nov 17
Total with taxes and fees
Godiluva, Weinvilla
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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Learn more about Pienza

The Renaissance town's perfectly preserved architecture frames spectacular views of Val d'Orcia from its ancient walls. Sample Pecorino cheese at small shops along cobblestone streets or join locals for aperitivo in Piazza Pio II.

See all hotels in Pienza
A historic town perched on a hillside with a prominent church tower, surrounded by lush greenery and rolling hills in the background.

Frequently Asked Questions

How much do villas in Pienza cost?

Rates for villas in Pienza range between $87 and $7,054 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 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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