Pienza Villas from CA $128

A historic square with a prominent tower and statues.

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Our top choices for Pienza villas

1. Podere Manafiore - historical villa with swimming pool

Monticchiello

Caroline R.

A stone building with a tiled roof, a small porch, and a pathway leading to it.

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

San Quirico d'Orcia

CA $2,863 total

includes taxes & fees

Sep 4 - Sep 5

A stone building with multiple rooms, surrounded by lush greenery and trees.

3. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

CA $2,579 total

includes taxes & fees

Sep 24 - Sep 25

An aerial view of a property with a large central building, a courtyard with a circular garden, and surrounding structures.

4. 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

CA $398 total

includes taxes & fees

Oct 2 - Oct 3

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

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

Torrita di Siena

CA $3,512 total

includes taxes & fees

Sep 6 - Sep 7

A stone building with a garden pathway leading to it.

6. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

CA $9,510 total

includes taxes & fees

Sep 17 - Sep 18

A patio with a table and chairs, a large umbrella, and a vase of flowers.

7. Villa Cielo- Cignella Resort Tuscany Accommodation

Trequanda

CA $464 total

includes taxes & fees

Oct 4 - Oct 5

A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

8. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

CA $8,756 total

includes taxes & fees

Sep 13 - Sep 14

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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Unique and beautifully appointed hotel. We loved our stay here. The spa is lovely and the food was fabulous. The staff are wonderful especially Allesandro, Federico, Orlando, Matteo and all the lovely staff at breakfast. The housekeeping staff were very friendly and we had an amazing time here. We stayed for 10 nights so got to know Cortona and the surrounding area very well."

Nuovo Etruria Resort

10/10 Excellent

"We had a lovely 3 night stay The pool area is just what’s needed to cool off in the afternoon The staff are friendly and helpful, it feels family run and they try to help wherever possible We walked into the old town from the hotel, it’s a steep walk uphill but if you have trouble walking I would recommend a vehicle The surrounding area is stunning Breakfast was good with options of hot and cold The bedroom was very clean, the bed was a little firm for my preference Highly Recommended"

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"It was a spectacular stay and so peaceful! All the staff were super helpful and the quality of service, amenities, and food really shined. Before we actually arrived, the staff would check in with us leading up to make sure we were all set up and all our requests answered. They also helped us prepare a wonderful birthday surprise for someone in our party."

Castello di Leonina Relais

10/10 Excellent

"We stayed 4 days and are so glad we stayed here. The area has a restaurant right outside with the best view where they serve lunch and dinner. They also have a bar and a pool. It’s an old castle and yet they keep it clean and pretty restored. Breakfast buffet in the morning was included for us. The bathroom comment from others might be from not understanding how to use it as you have to pump the button several times to flush. The staff was wonderful and helpful. They spoke English and some Spanish."

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."

Find out more about Pienza

Pienza Villas information

Number of reviews	109
Accommodation	1409 Villas
Lowest Price	CA $128
Highest Price	CA $9,510

Frequently asked questions

How much do villas in Pienza cost?

Rates for villas in Pienza range between CA $128 and CA $9,510 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 1409 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 $128

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza villas

1. Podere Manafiore - historical villa with swimming pool

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

3. WPRELAIS BORGO VIGNALUNGA

4. 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

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

6. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

7. Villa Cielo- Cignella Resort Tuscany Accommodation

8. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

9. Villa Falco-Cignella Resort Apartments in Tuscany

10. Artisti del Cavallo Tourism

11. Il Poggio dell'Eremita

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

13. Villa Aquila-Cignella Resort Acommodation Tuscany

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

15. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

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

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

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

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

20. Red Heart - relax with those you love in Tuscany.

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Find out more about Pienza

Pienza Villas information

Frequently asked questions

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