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Pienza Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Pienza holiday rentals

Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
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 HK$1,576
HK$1,788 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is HK$509
HK$588 total
includes taxes & fees
14 Dec - 15 Dec
Abbadia Sicille Relais
View from room
Tuscasì Aparthotel

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$513
HK$682 total
includes taxes & fees
14 Dec - 15 Dec
Tuscasì Aparthotel
Pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Siena

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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
Front of property – evening/night
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is HK$1,530
HK$1,720 total
includes taxes & fees
13 Dec - 14 Dec
Casanova - Panoramic Rooms and Suites
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is HK$1,106
HK$1,288 total
includes taxes & fees
14 Dec - 15 Dec
Il Poggio dell'Eremita
Outdoor dining
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Villa in chiusi

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
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
Exterior detail
The House of Alice, charm and relaxation

Holiday Home in Montalcino (SI)

The House of Alice, charm and relaxation
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 HK$1,365
HK$1,848 total
includes taxes & fees
11 Jan - 12 Jan 2026
The House of Alice, charm and relaxation
Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
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 HK$774
HK$888 total
includes taxes & fees
12 Jan - 13 Jan 2026
Bellarmino Boutique Apartments
Lobby
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is HK$745
HK$856 total
includes taxes & fees
15 Dec - 16 Dec
Residenza Fabroni
Outdoor pool
Gite Montemirello, with garden and swimming pool

Apartment in Casciano di Murlo - Siena

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

Villa in Montalcino

Villa in Montalcino, exclusive for you, stunning view!!!
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!!!
Property entrance
Il Tosco

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is HK$2,035
HK$2,275 total
includes taxes & fees
17 Dec - 18 Dec
Il Tosco
Outdoor pool
Farmhouse in the greenery of the Tuscany countryside with private pool and view

Holiday Home in Murlo

Farmhouse in the greenery of the Tuscany countryside with private pool and view
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
Outdoor pool
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Villa in Montisi

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
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!
Outdoor dining
Hilltop house in the heart of Tuscany with private pool

Villa in Montisi

Hilltop house in the heart of Tuscany with private pool
9.8 out of 10, Exceptional, (94)
"Lovely home with spectacular views! The home greatly exceeded our expectations. It had everything we needed for our 6 day. When not our touring the charming small Tuscany towns, we enjoyed the peace and quiet of the back porch and pool area. We kept the windows open and enjoyed the sweet breezes blowing through. If you're looking the perfect home to rent in Tuscany, this is the one. "
United States
Teresa G.
Hilltop house in the heart of Tuscany with private pool
Pool
Country House With Private Pool

Villa in Toscane

Country House With Private Pool
10.0 out of 10, Exceptional, (13)
"We had such a lovely week staying in this farmhouse just outside Citta della Pieve. The house itself and interiors are beautiful - the kitchen is well equipped, the beds are incredibly comfortable, the bathrooms modern, the pool is an excellent size, and the views are amazing. The hosts were incredibly friendly and generous, and really added to our overall experience. I would highly recommend a stay here - you will not be disappointed!"
United Kingdom
Clare C.
Country House With Private Pool
Pool
Villa Casale Silvia Large Private Pool, A/C, WiFi

Villa in Parrano

Villa Casale Silvia Large Private Pool, A/C, WiFi
9.4 out of 10, Exceptional, (22)
"A lovely escape - we enjoyed every moment!"
United States
Anonymous traveller
Villa Casale Silvia Large Private Pool, A/C, WiFi
Exterior
Osteria del Borgo

Residence in Montepulciano

Osteria del Borgo
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

Aparthotel in Siena

La Coroncina Lodging
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is HK$670
HK$774 total
includes taxes & fees
14 Dec - 15 Dec
La Coroncina Lodging
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

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 5 days ago
Abbadia Sicille Relais

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:

  • View our selection of featured holiday rentals in Pienza
  • Use the map to find apartments and other holiday homes in the Pienza neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pienza while they last

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

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?

The House of Alice, charm and relaxation: This holiday home rental outside of Pienza is located in a rural location, and has a fireplace, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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.