Pienza Holiday Rentals

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Holiday Rentals in Pienza

Hotel San Gregorio

3.0 star property
Pienza
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 NZ$366
includes taxes & fees
5 Dec - 6 Dec
Hotel San Gregorio

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

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

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (163)
"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 NZ$128
includes taxes & fees
4 Dec - 5 Dec
Abbadia Sicille Relais

Tuscasì Aparthotel

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 NZ$118
includes taxes & fees
8 Dec - 9 Dec
Tuscasì Aparthotel

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is NZ$368
includes taxes & fees
30 Nov - 1 Dec
Casanova - Panoramic Rooms and Suites

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

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

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

chiusi
10.0 out of 10, Exceptional, (55)
"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

Gite Montemirello, with garden and swimming pool

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

Bellarmino Boutique Apartments

Montepulciano
The price is NZ$156
includes taxes & fees
30 Nov - 1 Dec
Bellarmino Boutique Apartments

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (58)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is NZ$279
includes taxes & fees
1 Dec - 2 Dec
Il Poggio dell'Eremita

The House of Alice, charm and relaxation

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 NZ$429
includes taxes & fees
29 Nov - 30 Nov
The House of Alice, charm and relaxation

Hilltop house in the heart of Tuscany with private pool

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

Residenza Fabroni

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 NZ$161
includes taxes & fees
30 Nov - 1 Dec
Residenza Fabroni

Farmhouse in the greenery of the Tuscany countryside with private pool and view

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

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (113)
"Stunning views. Excellent hostess! Fabulous breakfast!! Would definitely stay again if ever back"
Canada
stephen
The price is NZ$473
includes taxes & fees
30 Nov - 1 Dec
Il Tosco

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

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!!!

Country House With Private Pool

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

Casina in authentic Tuscany

Cortona
9.8 out of 10, Exceptional, (69)
"The property was perfect. Lots of room, enough dishes and basic necessities. Wifi was good. Central to our adventures to Siena, Cortona, Perugia and Assisi over the duration of our visit. Thank you!"
Canada
Jeff W.
Casina in authentic Tuscany

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena
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

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
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 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 NZ$118 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?

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 33 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.