Pienza Vacation Rentals

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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

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
$106 nightly
The price is $121
Jun 16 - Jun 17
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 22 - Jun 23
Total with taxes and fees
Casa Gioia - Casa Olivieri
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
$169 nightly
The price is $174
Jun 7 - Jun 8
Total with taxes and fees
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
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
$189 nightly
The price is $215
Jun 17 - Jun 18
Total with taxes and fees
Hotel San Gregorio
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
$731 nightly
The price is $809
Jun 14 - Jun 15
Total with taxes and fees
L'Olmo
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.
$323 nightly
The price is $327
Jul 5 - Jul 6
Total with taxes and fees
Il Podere di Casa Rossa Pienza
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.
$163 nightly
The price is $167
Jun 11 - Jun 12
Total with taxes and fees
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
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
$105 nightly
The price is $120
Jun 9 - Jun 10
Total with taxes and fees
Il Pozzo di Sant'Andrea
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 $95
Jun 14 - Jun 15
Total with taxes and fees
RESIDENCE LECCIO
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
$91 nightly
The price is $105
Jun 7 - Jun 8
Total with taxes and fees
Villa Fontis Rapolano
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
$73 nightly
The price is $80
Jun 22 - Jun 23
Total with taxes and fees
La Dimora di Dida
Premium bedding, down comforters, pillowtop beds, minibar

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
$98 nightly
The price is $111
Jul 4 - Jul 5
Total with taxes and fees
Tuscasì Aparthotel
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
$86 nightly
The price is $94
Jun 6 - Jun 7
Total with taxes and fees
Agriturismo San Filippo
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
$92 nightly
The price is $102
Jun 7 - Jun 8
Total with taxes and fees
Le Roghete
Outdoor dining

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Panicale
$184 nightly
The price is $184
Jun 13 - Jun 14
Total with taxes and fees
Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
$94 nightly
The price is $94
Jun 7 - Jun 8
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
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
$83 nightly
The price is $96
Jun 8 - Jun 9
Total with taxes and fees
Residenza Fabroni
Terrace/patio

Holiday Home 'I Prati' with Private Pool, Private Terrace and Wi-Fi

Holiday Home 'I Prati' with Private Pool, Private Terrace and Wi-Fi
Elmo
$262 nightly
The price is $267
Jun 7 - Jun 8
Total with taxes and fees
Holiday Home 'I Prati' with Private Pool, Private Terrace and Wi-Fi
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (172 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
$106 nightly
The price is $126
Jun 24 - Jun 25
Total with taxes and fees
Bosco della Spina
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

Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Our stay here was great. Within walking distance to restaurants and the town. Pool water was cold, but we did enjoy it for a little bit. Had some issues worh no hot water, but it was resolved quickly. "
Carlos 1-night trip
Posted 2 days ago
Hotel San Gregorio

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 $96 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.