Pienza Holiday Rentals

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Holiday Rentals in Pienza

Residence in Pienza

3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is AU$357
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Villa in Pienza

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!"
United States
julie l.
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

Residence in Trequanda

4.0 star property
8.8 out of 10, Excellent, (164)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is AU$136
includes taxes & fees
21 Dec - 22 Dec
Abbadia Sicille Relais

Aparthotel in Sovicille

9.0 out of 10, Wonderful, (24)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AU$131
includes taxes & fees
13 Dec - 14 Dec
Tuscasì Aparthotel

Villa in Siena

9.4 out of 10, Exceptional, (67)
"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

Residence in San Quirico d'Orcia

3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is AU$322
includes taxes & fees
11 Dec - 12 Dec
Casanova - Panoramic Rooms and Suites

Villa in chiusi

10.0 out of 10, Exceptional, (57)
"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

Apartment in Casciano di Murlo - Siena

9.8 out of 10, Exceptional, (60)
"Very nice stay and very nuce Host :)"
Germany
Timo
Gite Montemirello, with garden and swimming pool

Apartment in Montepulciano

6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is AU$178
includes taxes & fees
10 Dec - 11 Dec
Bellarmino Boutique Apartments

Villa in Sinalunga

10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is AU$253
includes taxes & fees
19 Dec - 20 Dec
Il Poggio dell'Eremita

Holiday Home in Montalcino (SI)

9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is AU$385
includes taxes & fees
9 Dec - 10 Dec
The House of Alice, charm and relaxation

Villa in Montisi

9.8 out of 10, Exceptional, (94)
"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

Holiday Home in Murlo

9.6 out of 10, Exceptional, (52)
"Marina was a great host and the property was exactly what we were after!"
United Kingdom
Steph M.
Farmhouse in the greenery of the Tuscany countryside with private pool and view

Residence in Montepulciano

8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is AU$147
includes taxes & fees
8 Dec - 9 Dec
Residenza Fabroni

Villa in Montalcino

10.0 out of 10, Exceptional, (86)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Toscane

10.0 out of 10, Exceptional, (13)
"Beautiful property with the most amazing pool, our hosts were so lovely and helpful, always at hand if we needed anything. I would recommend for a very relaxing holiday."
United States
Maxine B.
Country House With Private Pool

Residence in Montepulciano

10.0 out of 10, Exceptional, (114)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is AU$534
includes taxes & fees
8 Dec - 9 Dec
Il Tosco

Villa in cortona

10.0 out of 10, Exceptional, (50)
"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

Apartment in Cortona

9.8 out of 10, Exceptional, (69)
"This was a perfect stay. Picturesque location, close to Cortona and wineries and shops- we even walked to one of them. Best of all though was the kindness of the host who left us wine, salad, bruschette and cantucci. We would LOVE to come back one day! "
Australia
Catherine G.
Casina in authentic Tuscany

Villa in Montisi

10.0 out of 10, Exceptional, (60)
"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!
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 AU$131 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 27 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.