Pienza Holiday Rentals from €79: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Pienza has to offer?

Agriturismo San Filippo : This holiday home rental outside of Pienza is located in the suburbs, and has a rooftop terrace, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and an espresso maker, so that you can cook with friends or family.

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Holiday Rentals in Pienza

Breakfast, lunch, dinner served; local cuisine

"Such friendly staff, loved Pienza and the property was such a good location! "

includes taxes & fees

25 Oct - 26 Oct

"The view from the house is spectacular! What a great spot for a group of friends or a large family. Close to vineyards and shopping. We love sitting on the back patio having dinner. The dog and cats were an extra. Lily and her husband were very helpful and we really enjoyed having the meals cooked by the chef while we were there. The last night with the fish was the best!"

"Beautiful historic villa. Loved the vibe. Would definitely stay here again! "

"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "

includes taxes & fees

29 Sept - 30 Sept

"Great Historical location."

includes taxes & fees

22 Oct - 23 Oct

"If you like a 360-degree view from the top of the hill, this is the place. Amazing views, out in the country with little traffic (more tractors than cars). Very private. We wanted to sit on the patio all day.The house is very comfortable and a good home base for sampling Brunello and visiting the Montalcino vineyards.Camilla was easy to communicate with before and during our stay."

"We enjoyed the scenery and service! Clean and comfortable. "

"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "

includes taxes & fees

1 Oct - 2 Oct

"Lovely villa in a beautiful location. "

"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "

"Exceptional service great building felt like a Medici!"

includes taxes & fees

29 Sept - 30 Sept

"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "

"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."

includes taxes & fees

30 Sept - 1 Oct

"Very nice stay and very nuce Host :)"

"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "

includes taxes & fees

29 Sept - 30 Sept

"That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price "

"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."

includes taxes & fees

11 Oct - 12 Oct

"We had five wonderful days in beautiful Toscana! Great atmosphere, wonderful location of the hotel and very reasonably priced. Eating at their restaurant was quite pricy however. Breakfast ok but excellent croissants and coffee! One of the reasons we picked this hotel was the laundry service which was advertised on hotels.com. No laundry service was available. "

includes taxes & fees

28 Sept - 29 Sept

"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."

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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Beautiful property, the staff were really friendly and helpful. "

Precise Tale Poggio Alla Sala

10/10 Excellent

"Wonderful surroundings, buildings and pools. The staff were attentive and the food just marvellous, both breakfast and evening meals. The only downside for us was that my elderly mother was visiting with us who found it difficult to get about as the buildings and pool are separate, it would have been good to have had an option for mum to be moved around in one of their electrical vehicles, and steps around the villa had no handrails so assistance was always required, but everything else was wonderful. "

Tenuta Santo Pietro

10/10 Excellent

"We had the most incredible stay at Tenuta Santo Pietro in Toscana! From the moment we arrived, we felt completely at home. Bertina, the manager, is truly the heartbeat of this place. She’s funny, full of energy, literally skipping around even after a long day, and never forgets a thing. Her attention to detail is impeccable, and she made us feel like old friends — chatting and laughing with her was one of the best parts of our trip. The rest of the staff is amazing too. Teresa and Micaela were always there, warm and attentive, making sure we were comfortable and well-fed. The estate itself is stunning, decorated in rustic Tuscan style, with a garden supplying fresh veggies for incredible homemade dishes — the pasta and ribollita soup were unforgettable. Their olive oil and wine, both produced on-site, are absolute highlights: the olive oil is the best we’ve ever had, and the wine is smooth, high-quality, and headache-free. Our room was beautiful, the bed super comfortable, and the shower had the strongest water pressure we’ve ever experienced. We rented e-bikes and explored Strada Querciassale — the views were breathtaking. The pool was perfect to cool off, and the entire property is impeccably maintained. Tenuta Santo Pietro is a rare gem where you feel pampered yet completely at home. Bertina and her team made our stay unforgettable — we’ll definitely be back!"

Hotel Dei Capitani

10/10 Excellent

"This was a fantastic place to stay while visiting Montalcino. Spectacular views from our room and from the breakfast area and pool deck. Staff was very hospitable, and the breakfast buffet was really good. Mimosa’s restaurant recommendations were on point😎. I picked this place somewhat randomly for me and my dad and did not regret it. Walking distance to great restaurants and gelato. Rooms are not elaborate, but you’re not there to stay in your room. A couple of suggestions: - if you put this place into Apple Maps or Google Maps, IT WILL SEND YOU UP A GRAVEL AGRICULTURAL ROAD WITH 20% GRADE, the Strada Communale Del Canaliccio. OMG, my heart was in my throat driving up this and we narrowly avoided an accident. Instead, ask Maps app to take you to Via Pietro Strozzi, then to the hotel. We made it safely, but there was some stress!! - there is very little permanent parking at the hotel. Drive there, drop your stuff, and they will give you a parking pass and directions to parking. - this may not be the place for those with severely limited mobility. The cobblestone roads are pretty steep. - if you need suggestions for wineries, there are so many, but Col D’Orcia won’t let you down. Book ahead.🍷"

Find out more about Pienza

Everything you need to know about Pienza holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pienza holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pienza holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pienza. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza holiday rentals we have selected for you start as low as €79 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pienza rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pienza holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pienza. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Pienza?

Yes, there are holiday rentals in Pienza close to RI Crea RE, or you can select a more secluded option if you're looking for a relaxing stay. Pienza is known for its churches and wineries. Make sure you have time to check out the temples while you're in the area.

What are some of the best holiday rentals that Pienza has to offer?

Agriturismo San Filippo: This holiday home rental outside of Pienza is located in the suburbs, and has a rooftop terrace, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and an espresso maker, so that you can cook with friends or family.

How many holiday rentals are there in Pienza?

Expedia has 30 holiday rentals for your stay in Pienza.

What’s there to see and do in Pienza?

Cultural attractions include Palazzo Borgia and Artemisia Gallery, whereas Historic Centre of Pienza and Val di Chiana are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Palazzo Piccolomini and Pienza Cathedral.

What’s a holiday rental in Pienza like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pienza. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.

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Holiday Rentals in Pienza

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Holiday Rentals in Pienza

Hotel San Gregorio

Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

Luxury Privacy in the Heart of Tuscany

Casanova - Panoramic Rooms and Suites

Abbadia Sicille Relais

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Bosco della Spina

Tuscasì Aparthotel

Villa in Montalcino, exclusive for you, stunning view!!!

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Delcorto Suites

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Residenza Fabroni

Gite Montemirello, with garden and swimming pool

Il Tosco

Porta Pispini Residence

Il Poggio dell'Eremita

Borgo Dolciano

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Precise House Montaperti Siena

Hotel Corsignano

Hotel Certosa Di Maggiano

Fonteverde Lifestyle & Thermal Retreat

Precise Tale Poggio Alla Sala

Tenuta Santo Pietro

Hotel Dei Capitani

Nuovo Etruria Resort

Find out more about Pienza

Frequently asked questions

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