Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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
$680 nightly
The price is $753
Jul 13 - Jul 14
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, (146 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
$185 nightly
The price is $210
Jun 14 - Jun 15
Total with taxes and fees
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
$120 nightly
The price is $136
Jun 21 - Jun 22
Total with taxes and fees
PienzaLettings Suites
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
$94 nightly
The price is $108
Jun 14 - Jun 15
Total with taxes and fees
TuscanyLettings Studio&Room
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
$122 nightly
The price is $139
Jun 29 - Jun 30
Total with taxes and fees
Casa Gioia - Casa Olivieri
Suite, Multiple Beds, Valley View | Bathroom | Shower, rainfall showerhead, designer toiletries, hair dryer

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (144 reviews)
"Great location."
United States
James
$139 nightly
The price is $158
Jun 28 - Jun 29
Total with taxes and fees
La Locanda di San Francesco
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
$77 nightly
The price is $89
Jun 14 - Jun 15
Total with taxes and fees
Villa Fontis Rapolano
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (137 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
$134 nightly
The price is $152
Jul 9 - Jul 10
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
$80 nightly
The price is $88
Jun 13 - Jun 14
Total with taxes and fees
Agriturismo San Filippo
Massages

Chalet Il Cristallo

Chalet Il Cristallo
Castel del Piano
7.6 out of 10, Good, (4 reviews)
"Camera impeccabile, personale cortese e disponibile, colazione ottima ,come la cena. Struttura molto accogliente. Ottima per famiglie."
Italy
Federico
$48 nightly
The price is $57
Jun 22 - Jun 23
Total with taxes and fees
Chalet Il Cristallo
Shared fridge, microwave

Affittacamere I Canneggiatori

Affittacamere I Canneggiatori
Abbadia San Salvatore
8.6 out of 10, Excellent, (9 reviews)
"Very stylish, modern, well equipped apartment. Close to everything. Bed is okay, had a relaxing sleep. Good size bathroom with toilet. Staff who came to clean daily was very helpful, supportive, kind. Parking on the street in from of the building. "
United Kingdom
Erika
$82 nightly
The price is $90
Jul 12 - Jul 13
Total with taxes and fees
Affittacamere I Canneggiatori
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, (90 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
$167 nightly
The price is $189
Jul 12 - Jul 13
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (37 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
$178 nightly
The price is $200
Jun 13 - Jun 14
Total with taxes and fees
Delcorto Suites
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (107 reviews)
"Place is amazing and maintained perfectly."
United States
Dominic
$164 nightly
The price is $185
Jul 1 - Jul 2
Total with taxes and fees
Meublé Il Riccio
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
$101 nightly
The price is $115
Jun 16 - Jun 17
Total with taxes and fees
Il Pozzo di Sant'Andrea
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 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
$86 nightly
The price is $99
Jun 30 - Jul 1
Total with taxes and fees
Residenza Fabroni
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (67 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
$124 nightly
The price is $146
Jun 21 - Jun 22
Total with taxes and fees
Villa Curina Resort
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
$72 nightly
The price is $79
Jun 16 - Jun 17
Total with taxes and fees
La Dimora di Dida
Property entrance

Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very Good, (17 reviews)
"To far out"
United States
Dennis
$106 nightly
The price is $121
Jun 16 - Jun 17
Total with taxes and fees
Castello di Modanella
Exterior

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (93 reviews)
"Great location, nice room, and great host!"
United States
Chris
$144 nightly
The price is $163
Jul 3 - Jul 4
Total with taxes and fees
B&B Le Scalette di Piazza
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
"The staff are fantastic! Everyone is at your service with whatever your needs are. A historical gem with such rich history. We were in awe."
mathew 7-night trip
Posted 1 day ago
Monastero di Cortona Hotel & Spa

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 $99 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.