A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Pienza vacation rentals

Laptop workspace, iron/ironing board, WiFi (free)

1. 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 P6,309
P7,222 total
includes taxes & fees
Aug 12 - Aug 13
TuscanyLettings Studio&Room
Terrace/patio

2. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is P6,688
P7,638 total
includes taxes & fees
Aug 12 - Aug 13
PienzaLettings Suites
Exterior

3. 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 P7,927
P9,001 total
includes taxes & fees
Aug 31 - Sep 1
Casa Gioia - Casa Olivieri
Food and drink

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is P13,418
P15,182 total
includes taxes & fees
Aug 13 - Aug 14
Hotel San Gregorio
Courtyard view

5. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is P44,390
P49,111 total
includes taxes & fees
Aug 16 - Aug 17
L'Olmo
Couples treatment rooms, sauna, hot tub, steam room, body treatments

6. 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, (49 reviews)
"Our stay was great. "
United States
Elena
The price is P6,953
P7,931 total
includes taxes & fees
Aug 11 - Aug 12
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Food court

7. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is P8,648
P9,794 total
includes taxes & fees
Aug 27 - Aug 28
La Locanda di San Francesco
Exterior

8. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 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 P7,293
P8,304 total
includes taxes & fees
Aug 11 - Aug 12
Bed & Breakfast Vicolo dell'Oste
1 treatment room, massages

9. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is P10,710
P12,063 total
includes taxes & fees
Aug 30 - Aug 31
Casanova - Panoramic Rooms and Suites
Property entrance

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 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 P4,753
P5,510 total
includes taxes & fees
Aug 18 - Aug 19
Residenza Fabroni
Front of property

11. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful place, view and city."
United States
Federico
The price is P7,091
P8,082 total
includes taxes & fees
Aug 11 - Aug 12
montorio
Interior

12. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is P10,041
P11,326 total
includes taxes & fees
Aug 11 - Aug 12
Meublé Il Riccio
Terrace/patio

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P12,433
P13,888 total
includes taxes & fees
Aug 24 - Aug 25
Abbadia Sicille Relais
Front of property

14. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
5.6 out of 10, (4 reviews)
"I wish I knew more about the check in process ahead of time of that they contacted me ok WhatsApp. But it was clean, comfortable, as pictured, great location, and a great stay. "
United States
Nicole
The price is P4,567
P5,305 total
includes taxes & fees
Aug 31 - Sep 1
Bellarmino Boutique Apartments
Breakfast, lunch and dinner served

15. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! The staff are exceptional- so helpful and kind with every aspect of the stay. The rooms are beautiful and lovely amenities upon arrival. Would definitely go back again!"
United States
Victoria
The price is P19,944
P22,502 total
includes taxes & fees
Aug 25 - Aug 26
Palazzo Saloni
Terrace/patio

16. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is P10,740
P12,096 total
includes taxes & fees
Aug 12 - Aug 13
Delcorto Suites
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

Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"Beautiful stay here. Restaurant was fantastic and they prepared special dishes to meet our vegetarian needs. Buffet breakfast with fresh cappuccinos was wonderful. Room was impeccably clean with daily cleaning service. This was our second time here and we are hoping to return to this authentic Tuscany resort. You will likely not find a better place to stay at in Tuscany."
Karen 4-night trip
Posted 1 day ago
Agriturismo La Sovana

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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Frequently asked questions

Can I find a vacation rental in Pienza?

Yes, we give you a choice of vacation rentals in Pienza close to RI Crea RE, 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 29 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 Pienza Cathedral and Palazzo Piccolomini.

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.