A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Pienza vacation rentals

Exterior detail

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Pienza
The price is ￥17,566
￥21,986 total
includes taxes & fees
Jul 1 - Jul 2
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Exterior

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 ￥20,300
￥23,067 total
includes taxes & fees
Jul 29 - Jul 30
Casa Gioia - Casa Olivieri
Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi

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 ￥16,355
￥18,728 total
includes taxes & fees
Jul 17 - Jul 18
TuscanyLettings Studio&Room
Suite, 2 Bedrooms | Courtyard view

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 ￥73,652
￥81,754 total
includes taxes & fees
Jul 27 - Jul 28
L'Olmo
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (148 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ￥34,824
￥39,411 total
includes taxes & fees
Jul 22 - Jul 23
Hotel San Gregorio
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (4 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ￥17,421
￥19,903 total
includes taxes & fees
Jul 1 - Jul 2
PienzaLettings Suites
1 bedroom, iron/ironing board, WiFi

Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Pienza
8.0 out of 10, Very Good, (1 review)
"Very nice property and easily walkable to all of Pienza. It was also a convenient base to explore the Tuscany region. The property was clean and the bed was comfortable. A lot of restaurants and shopping in less than a 5 minute walk. The photos of the apartment were accurate. I would add to the property description that parking is not at the property but public parking is nearby (for clarity).Overall, I was happy with my stay."
United States
Michael H.
The price is ￥23,976
￥30,636 total
includes taxes & fees
Jul 7 - Jul 8
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Outdoor dining

Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is ￥33,300
￥49,210 total
includes taxes & fees
Jul 5 - Jul 6
Il Podere di Casa Rossa Pienza
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is ￥12,528
￥14,518 total
includes taxes & fees
Jul 2 - Jul 3
Villa Fontis Rapolano
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ￥17,668
￥20,174 total
includes taxes & fees
Jul 6 - Jul 7
Il Pozzo di Sant'Andrea
Junior Suite | Terrace/patio

Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is ￥17,802
￥20,323 total
includes taxes & fees
Jul 1 - Jul 2
Casale dell'Assiolo
Premium bedding, down comforters, pillowtop beds, individually furnished

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥12,090
￥15,693 total
includes taxes & fees
Jul 7 - Jul 8
Tuscasì Aparthotel
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
The price is ￥13,373
￥14,710 total
includes taxes & fees
Jul 8 - Jul 9
Agriturismo San Filippo
Classic Apartment, Vineyard View | Interior

Podere Tre Berte - The Sleeping Beauty

Podere Tre Berte - The Sleeping Beauty
Toscana
The price is ￥12,956
￥14,251 total
includes taxes & fees
Jul 22 - Jul 23
Podere Tre Berte - The Sleeping Beauty
Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,600
￥14,914 total
includes taxes & fees
Jul 1 - Jul 2
Holiday home with panoramic terrace ideal for families and couples
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is ￥12,942
￥15,161 total
includes taxes & fees
Jul 20 - Jul 21
RESIDENCE LECCIO
Pool

Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is ￥27,620
￥62,236 total
includes taxes & fees
Jul 3 - Jul 4
Agritourism in val d'orcia
Exterior

Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (6 reviews)
"Loved everything about my stay"
United States
Svetlana
The price is ￥23,029
￥27,182 total
includes taxes & fees
Jul 9 - Jul 10
Corte Francigena - Apartments
Exterior

Le Roghete

Le Roghete
Acquapendente
9.4 out of 10, Exceptional, (3 reviews)
"The address of the hotel was wrong on the Hotels.com web site. After an anxious hour or so our host was kind enough to come and get us, we were on foot walking the Via Francigena and the additional 4 miles back would have been a killer. Our host arranged for a cab the next morning so we were back on schedule. Worth the cab expense to keep on schedule. Wonderful evening meal and a great hotel. I would visit it again."
United States
Mark
The price is ￥14,337
￥15,771 total
includes taxes & fees
Jul 7 - Jul 8
Le Roghete
BBQ/picnic area

Residenza d'epoca Ca' de Principi

Residenza d'epoca Ca' de Principi
Piegaro
9.8 out of 10, Exceptional, (13 reviews)
"The hotel was charming, and the staff really nice. Breakfast had lots of options. The room was large and beautiful view of the hills. The bed was comfortable."
United States
Robyn
The price is ￥21,761
￥23,937 total
includes taxes & fees
Jul 1 - Jul 2
Residenza d'epoca Ca' de Principi
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"This is an excellent hotel, great staff, great location and great food. The breakfast is a really nice experience and the courtyard swimming pool is so peaceful."
Timothy 3-night trip
Posted 18 hours ago
Monastero di Cortona Hotel & Spa

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 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.

What are some of the best vacation home rentals in Pienza?

The House of Alice, charm and relaxation: This vacation home rental near 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 an electric kettle. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Pienza?

Expedia has 27 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.