A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pienza vacation rentals

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

1. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (165 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is NT$4,133
NT$4,765 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
A patio area with outdoor seating, potted plants, and a view of the landscape.

2. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (73 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is NT$3,534
NT$4,795 total
includes taxes & fees
Oct 28 - Oct 29
Affitacamere Maria Gabriella
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

3. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (6 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is NT$2,629
NT$3,038 total
includes taxes & fees
Nov 2 - Nov 3
PienzaLettings Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

4. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is NT$2,863
NT$3,295 total
includes taxes & fees
Nov 2 - Nov 3
TuscanyLettings Studio&Room
A stone building with a wooden door, a staircase, and a small window with a metal grill.

5. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is NT$3,690
NT$4,205 total
includes taxes & fees
Oct 28 - Oct 29
Casa Gioia - Casa Olivieri
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

6. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is NT$14,579
NT$16,183 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A poolside area with two glasses of water, candles, and a stone pathway.

7. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (102 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is NT$5,832
NT$6,561 total
includes taxes & fees
Oct 22 - Oct 23
Casanova - Panoramic Rooms and Suites
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

8. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is NT$4,175
NT$4,738 total
includes taxes & fees
Nov 9 - Nov 10
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A historic building with a tower, a courtyard, and a well-lit entrance.

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is NT$2,848
NT$3,243 total
includes taxes & fees
Nov 17 - Nov 18
Abbadia Sicille Relais
A stone building with a courtyard, outdoor seating, and a warm light setting.

10. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is NT$3,612
NT$4,410 total
includes taxes & fees
Nov 3 - Nov 4
Sarna Residence
A crowded restaurant with brick walls and multiple tables and chairs.

11. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (151 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is NT$4,606
NT$5,212 total
includes taxes & fees
Nov 3 - Nov 4
La Locanda di San Francesco
Front of property

12. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful place, view and city."
United States
Federico
The price is NT$3,668
NT$4,181 total
includes taxes & fees
Oct 22 - Oct 23
montorio
A snow-covered town with traditional buildings and a mountainous backdrop.

13. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is NT$5,194
NT$5,859 total
includes taxes & fees
Oct 22 - Oct 23
Meublé Il Riccio
A terrace with a table set for breakfast, overlooking a scenic landscape.

14. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (48 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is NT$6,173
NT$6,936 total
includes taxes & fees
Oct 25 - Oct 26
Delcorto Suites
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

15. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (137 reviews)
"An amazing property with amazing hosts! Every detail was an amenity was thought of. Hosts are very gracious and bend over backwards to make your stay unforgettable!"
Canada
Sean
The price is NT$7,515
NT$8,412 total
includes taxes & fees
Nov 2 - Nov 3
Il Tosco
An arched doorway leading to a building with a wooden door and a staircase.

16. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (114 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is NT$2,602
NT$3,008 total
includes taxes & fees
Oct 23 - Oct 24
Residenza Fabroni
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

17. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is NT$3,430
NT$3,918 total
includes taxes & fees
Nov 1 - Nov 2
Bed & Breakfast Vicolo dell'Oste
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

18. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is NT$8,519
NT$9,737 total
includes taxes & fees
Nov 2 - Nov 3
Palazzo Saloni
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

19. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is NT$3,877
NT$4,410 total
includes taxes & fees
Nov 8 - Nov 9
B&B Le Scalette di Piazza
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

20. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is NT$2,979
NT$3,569 total
includes taxes & fees
Nov 14 - Nov 15
Idolina Guest House
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

Fonteverde Thermal Spa Resort Tuscany

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent
"Unbelievable view! And the rooms were very clean and large. I hope we get the opportunity to make it back to this hotel one day!"
Rebecca 2-night trip
Posted 2 hours ago
Fonteverde Thermal Spa Resort Tuscany

Find out more about Pienza

Search for holiday rentals in Pienza on Expedia! You can easily find your home rentals, villas, holiday apartments in Pienza using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pienza!

Frequently asked questions

Can I find a vacation rental in Pienza?

Yes, we give you a choice of vacation rentals in Pienza close to Art Studio di Adelina Quadri, or you can go with a secluded option if you want 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.

How many vacation rentals are there in Pienza?

Expedia has 30 vacation 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 vacation rental in Pienza like?

Vacation rentals are private properties you can book for a long or short time in Pienza. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.