Best Pienza Villas: Private & Luxury Villa Accommodations in Pienza

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.

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

San Quirico d'Orcia

includes taxes & fees

16 Sept - 17 Sept

3. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

includes taxes & fees

24 Sept - 25 Sept

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

includes taxes & fees

7 Oct - 8 Oct

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

Torrita di Siena

includes taxes & fees

14 Sept - 15 Sept

6. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

Chris S.

includes taxes & fees

11 Oct - 12 Oct

7. Villa Falco-Cignella Resort Apartments in Tuscany

Trequanda

includes taxes & fees

28 Sept - 29 Sept

8. Il Poggio dell'Eremita

Sinalunga

Paul Q.

includes taxes & fees

15 Sept - 16 Sept

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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"I never write hotel reviews, but this hotel was so exceptional that I had to share my experience. The room was beautiful, spotless, and incredibly comfortable, with thoughtful turn-down service every evening. The staff were truly the most attentive and welcoming I’ve ever experienced. They helped arrange pickup from the train station, made restaurant reservations, and went above and beyond in so many little ways. Those small details made me feel genuinely cared for. The breakfast was lovely and served in such a beautiful setting — the perfect way to start the day. I absolutely loved my stay here and would come back to Cortona for this hotel alone. A truly special place with exceptional hospitality. Highly recommend!"

Hotel Corsignano

10/10 Excellent

"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot for us. That level of thoughtfulness and hospitality really stood out. The hotel was exceptionally clean and in a fantastic location, just a few steps from the historic center of Pienza. And the breakfast was wonderful, with plenty of delicious options to choose from. We truly felt welcomed and well taken care of throughout our stay. We would happily stay here again and highly recommend Hotel Corsignano!"

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

Find out more about Pienza

Pienza Villas information

Number of reviews	172
Accommodation	1223 Villas
Lowest Price	AU$134
Highest Price	AU$9,591

Frequently asked questions

How much do villas in Pienza cost?

Villas in Pienza cost between AU$134 and AU$9,591 per night. These getaways provide the privacy to enjoy your own space at a price that's gentle to your wallet. This price was 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?

Reclaim your holiday days and pick from 1223 villas in Pienza. For a family holiday, a couple's getaway and everything in between, Expedia will help you find the right place in just a click or two.

What is there to do near my villa in Pienza?

Pienza has enough experiences and sights to keep you occupied for weeks, starting with Pienza Cathedral. Piscine Termali Theia, Terme di Montepulciano Spa and Tenuta Greppo Franco Biondi Santi are other awesome attractions. If you're hanging around a while, Palazzo Piccolomini and Consorzio del Vino Nobile di Montepulciano will add the finishing touches to your itinerary.

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Search Pienza Villa Accommodation

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. Wp Relais Villa Vignalunga

7. Villa Falco-Cignella Resort Apartments in Tuscany

8. Il Poggio dell'Eremita

9. Villa Cielo- Cignella Resort Tuscany Accommodation

10. Artisti del Cavallo Tourism

11. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

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

13. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

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

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

16. 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

17. Villa Aquila-Cignella Resort Acommodation Tuscany

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

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

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

Find holiday 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

Explore a world of travel with Expedia