Pienza Holiday Rentals

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Holiday Rentals in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (130)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is AU$217
includes taxes & fees
4 Nov - 5 Nov
Hotel San Gregorio
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
10.0 out of 10, Exceptional, (4)
"Beautiful historic villa. Loved the vibe. Would definitely stay here again! "
United States
Mark Y.
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (75)
"Fantastic place"
United States
Clifford
The price is AU$308
includes taxes & fees
26 Oct - 27 Oct
Casanova - Panoramic Rooms and Suites
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (160)
"It was too cold for the swimming pool as it is mid October, there were people using the hot tub, but I have one in my room and the sauna so why bother it was so wonderful and the staff was super. Christina was the most wonderful ball."
United States
Christine
The price is AU$121
includes taxes & fees
2 Nov - 3 Nov
Abbadia Sicille Relais
Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (84)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
9.4 out of 10, Exceptional, (66)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.6 out of 10, Exceptional, (72)
"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! "
United States
Rainey M.
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Tuscasì Aparthotel
9.2 out of 10, Wonderful, (22)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AU$133
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel
Residenza Fabroni
8.8 out of 10, Excellent, (90)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
Canada
Nicole
The price is AU$142
includes taxes & fees
20 Oct - 21 Oct
Residenza Fabroni
Bellarmino Boutique Apartments
The price is AU$190
includes taxes & fees
4 Nov - 5 Nov
Bellarmino Boutique Apartments
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (53)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Bosco della Spina
9.6 out of 10, Exceptional, (166)
"We enjoyed the scenery and service! Clean and comfortable. "
United States
Sanaz
Bosco della Spina
Hilltop house in the heart of Tuscany with private pool
9.8 out of 10, Exceptional, (93)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
United States
Timothy C.
Hilltop house in the heart of Tuscany with private pool
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (57)
"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."
United States
Vivian K.
The price is AU$251
includes taxes & fees
22 Oct - 23 Oct
Il Poggio dell'Eremita
The House of Alice, charm and relaxation
9.8 out of 10, Exceptional, (66)
"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "
Canada
Debbie W.
The price is AU$392
includes taxes & fees
20 Oct - 21 Oct
The House of Alice, charm and relaxation
Gite Montemirello, with garden and swimming pool
9.8 out of 10, Exceptional, (60)
"Very nice stay and very nuce Host :)"
Germany
Timo
Gite Montemirello, with garden and swimming pool
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 "
United States
Michael
The price is AU$482
includes taxes & fees
9 Nov - 10 Nov
Il Tosco
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
10.0 out of 10, Exceptional, (57)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
United States
Darrel W.
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
10.0 out of 10, Exceptional, (9)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
United Kingdom
Marc K.
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Luxury Cortona view hilltop Villa
10.0 out of 10, Exceptional, (48)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Australia
Belinda P.
Luxury Cortona view hilltop Villa
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

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, 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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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?

Villa I Cipressini Tuscany Private luxury pool spa: This highly rated holiday home rental in Pienza offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Pienza?

Expedia has 32 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.