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Top Holiday Rentals in Pienza

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (123)
"Such friendly staff, loved Pienza and the property was such a good location! "
Hotel San Gregorio

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

10.0 out of 10, Exceptional, (2)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

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

9.6 out of 10, Exceptional, (17)
"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!"
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

Luxury Privacy in the Heart of Tuscany

Luxury Privacy in the Heart of Tuscany

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (65)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
The price is £150
includes taxes & fees
7 Sept - 8 Sept
Casanova - Panoramic Rooms and Suites

Il Casale Di Manuele 12, Emma Villas

10.0 out of 10, Exceptional, (3)
"We loved this home - everything was perfect and it was easy to find and enjoy. I highly recommend the next time you are wanting to stay in Tuscany! "
Il Casale Di Manuele 12, Emma Villas

Bosco della Spina

9.6 out of 10, Exceptional, (162)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina

Residenza Fabroni

8.8 out of 10, Excellent, (89)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
The price is £77
includes taxes & fees
28 Aug - 29 Aug
Residenza Fabroni

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is £142
includes taxes & fees
31 Aug - 1 Sept
Abbadia Sicille Relais

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (19)
"Very clean and comfortable accommodations. Beautiful view of the countryside!"
The price is £66
includes taxes & fees
16 Sept - 17 Sept
Tuscasì Aparthotel

Delcorto Suites

10.0 out of 10, Exceptional, (25)
"Exceptional service great building felt like a Medici!"
The price is £169
includes taxes & fees
27 Aug - 28 Aug
Delcorto Suites

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

10.0 out of 10, Exceptional, (83)
"The villa is huge and well appointed with anything you could imagine There are two large dining rooms inside and several well appointed outside patio areas. The bucolic setting includes birds , roaming sheep down the hill meandering from field to field. Couldn’t be more restful! Also close enough to Siena , San gimingnano Assisi for day trips and even Florence Will definitely return. "
Villa in Montalcino, exclusive for you, stunning view!!!

Il Tosco

10.0 out of 10, Exceptional, (112)
"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 "
The price is £233
includes taxes & fees
10 Sept - 11 Sept
Il Tosco

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

9.6 out of 10, Exceptional, (70)
"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! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

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

9.4 out of 10, Exceptional, (61)
"We wanted to enjoy the Tuscany area and this house checked all the boxes for us. The photos can’t actually capture the true beauty of this place. The host, Camilla was so gracious and kind. Comfortable bed, kitchen well stocked with the dishes we needed. Full size refrigerator was nice too! It’s a little bit of a drive to the property but oh so worth it! "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

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

10.0 out of 10, Exceptional, (52)
"we had a amazing time staying at this beautiful Villla. I highly recommend it to anyone!"
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Porta Pispini Residence

2.0 star property
9.6 out of 10, Exceptional, (17)
"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 "
Porta Pispini Residence

La Coroncina Lodging

10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
The price is £101
includes taxes & fees
28 Aug - 29 Aug
La Coroncina Lodging

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa

Borgo Dolciano

9.0 out of 10, Wonderful, (24)
"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. "
The price is £84
includes taxes & fees
1 Sept - 2 Sept
Borgo Dolciano
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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Top Pienza Hotel Reviews

Find out more about Pienza

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 £66 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?

Your dream home! In harmony with nature! Priv. Pool - fantastic views!: This holiday home rental outside of Pienza is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Pienza?

Expedia has 28 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.