Pienza Vacation Rentals

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Pienza vacation rentals

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
$726 nightly
The price is $803
Jun 14 - Jun 15
Total with taxes and fees
L'Olmo
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (145 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
$172 nightly
The price is $196
Jun 7 - Jun 8
Total with taxes and fees
Hotel San Gregorio
Exterior

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (2 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
$121 nightly
The price is $138
Jun 22 - Jun 23
Total with taxes and fees
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, (2 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
$105 nightly
The price is $120
Jun 14 - Jun 15
Total with taxes and fees
TuscanyLettings Studio&Room
Fridge, microwave, stovetop, dishwasher

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (9 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
$136 nightly
The price is $141
Jun 17 - Jun 18
Total with taxes and fees
"Il Focolare" Superior Apartment in Monticchiello
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
$168 nightly
The price is $173
Jun 8 - Jun 9
Total with taxes and fees
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
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
$117 nightly
The price is $133
Jun 8 - Jun 9
Total with taxes and fees
PienzaLettings Suites
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.
$306 nightly
The price is $311
Jun 9 - Jun 10
Total with taxes and fees
Il Podere di Casa Rossa Pienza
2 bedrooms, desk, iron/ironing board, travel crib

The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay."
United States
Melissa B.
$142 nightly
The price is $144
Jun 23 - Jun 24
Total with taxes and fees
The house in the village - Angelica apartment - Vald'Orcia
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.
$161 nightly
The price is $166
Jun 11 - Jun 12
Total with taxes and fees
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
$285 nightly
The price is $321
Jun 11 - Jun 12
Total with taxes and fees
2 Cuori e 1 Yurta Glamping in Toscana
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
$104 nightly
The price is $119
Jun 9 - Jun 10
Total with taxes and fees
Il Pozzo di Sant'Andrea
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (66 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
$129 nightly
The price is $152
Jun 21 - Jun 22
Total with taxes and fees
Villa Curina Resort
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (88 reviews)
"We loved our stay and wish we could have stayed longer. Our room was clean & comfortable. The view was AMAZING. We had breakfast included daily which was very good and had a bunch of gluten free options. Our bodies were tired after the hustle & bustle of Florence & Rome so we booked into the “light spa” and had the hot pools to ourselves. It was a short walk to town. We wish we could have stayed longer and plan to be back. "
Canada
Ron
$172 nightly
The price is $194
Jun 11 - Jun 12
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
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
$81 nightly
The price is $94
Jun 24 - Jun 25
Total with taxes and fees
RESIDENCE LECCIO
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
$136 nightly
The price is $150
Jun 7 - Jun 8
Total with taxes and fees
Residenza d'epoca Ca' de Principi
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
$196 nightly
The price is $219
Jun 8 - Jun 9
Total with taxes and fees
Abbadia Sicille Relais
Interior detail

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
$132 nightly
The price is $150
Jun 8 - Jun 9
Total with taxes and fees
La Coroncina Lodging
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
$118 nightly
The price is $132
Jun 19 - Jun 20
Total with taxes and fees
La Piccola Locanda
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
$84 nightly
The price is $93
Jun 7 - Jun 8
Total with taxes and fees
Agriturismo San Filippo
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

Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"The location is beautiful, featuring a stunning view of Pienza in the distance. We had both breakfast and dinner on site twice and the food and wine were very very good. Bertinna treated us very well and the entire staff was very welcoming. This is a very relaxing and comfortable place to stay in Tuscany."
Brian 3-night trip
Posted 1 day ago
Tenuta Santo Pietro

Find out more about Pienza

Everything you need to know about Pienza vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pienza vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pienza in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $98 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Podere Casorbica with free parking, large garden, private pool.: This vacation home rental near Pienza is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a balcony and a garden.

How many vacation rentals are there in Pienza?

Expedia has 28 vacation rentals for your stay in Pienza.

What’s there to see and do in Pienza?

Cultural attractions include Artemisia Gallery and Palazzo Borgia, 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.