Pienza Vacation Rentals

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Jul 20 - Jul 21
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Jul 25 - Jul 27
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Aug 1 - Aug 3

Vacation Rentals in Pienza

Hotel San Gregorio
Enjoy dining under a shaded pergola surrounded by lush greenery and brick walls.

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (119)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."
Hotel San Gregorio
Casanova - Panoramic Rooms and Suites
Relax by the serene pool surrounded by lush greenery and lounge under the shade of umbrellas.

Casanova - Panoramic Rooms and Suites

3.0 star property
9.2 out of 10, Wonderful, (61)
"Excellent views and the property was overall lovely. The nearby town San Quirico d'Orcia also had a good selection of restaurants and was a nice place to stroll in the evening."
The price is NT$5,557
NT$6,250 total
includes taxes & fees
Jul 23 - Jul 24
Casanova - Panoramic Rooms and Suites
Bosco della Spina
Surrounded by lush greenery and vineyards, this traditional complex offers a tranquil setting with a swimming pool and sun loungers.

Bosco della Spina

9.6 out of 10, Exceptional, (158)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina
Abbadia Sicille Relais
Relax in a serene outdoor space surrounded by lush greenery and tall trees, featuring a cozy fire pit and comfortable seating.

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is NT$4,557
NT$5,115 total
includes taxes & fees
Jul 21 - Jul 22
Abbadia Sicille Relais
Il Tosco
Wander through historic streets lined with traditional stone buildings and arched doorways.

Il Tosco

10.0 out of 10, Exceptional, (111)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
The price is NT$8,574
NT$9,568 total
includes taxes & fees
Jul 26 - Jul 27
Il Tosco
Tuscasì Aparthotel
Enjoy dining al fresco on this scenic outdoor terrace with a table set amidst a serene natural backdrop.

Tuscasì Aparthotel

9.4 out of 10, Exceptional, (18)
" Very nice, clean and big apartment. Great location and very friendly staff. Safe parking. "
The price is NT$2,604
NT$2,865 total
includes taxes & fees
Aug 13 - Aug 14
Tuscasì Aparthotel
Residenza Fabroni
Stunning staircase with a grand, curved ceiling and elegant details.

Residenza Fabroni

8.8 out of 10, Excellent, (86)
"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."
The price is NT$2,822
NT$3,241 total
includes taxes & fees
Jul 24 - Jul 25
Residenza Fabroni
Corte Francigena
Enjoy a spacious living area with a high ceiling, kitchen, dining table, and sofa, offering a view of the surrounding mountains.

Corte Francigena

10.0 out of 10, Exceptional, (5)
"Loved everything about my stay"
The price is NT$5,759
NT$6,745 total
includes taxes & fees
Jul 31 - Aug 1
Corte Francigena
Porta Pispini Residence
Relax in a stylish outdoor space with comfortable seating areas and a staircase leading to an upper level.

Porta Pispini Residence

2.0 star property
9.6 out of 10, Exceptional, (16)
"That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price "
Porta Pispini Residence
Borgo Dolciano
Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

Borgo Dolciano

9.0 out of 10, Wonderful, (24)
"We had five wonderful days in beautiful Toscana! Great atmosphere, wonderful location of the hotel and very reasonably priced. Eating at their restaurant was quite pricy however. Breakfast ok but excellent croissants and coffee! One of the reasons we picked this hotel was the laundry service which was advertised on hotels.com. No laundry service was available. "
The price is NT$3,394
NT$3,802 total
includes taxes & fees
Jul 24 - Jul 25
Borgo Dolciano
Osteria del Borgo
Enjoy a panoramic view of the rolling hills and stone tower from the large arched window.

Osteria del Borgo

9.2 out of 10, Wonderful, (145)
"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "
The price is NT$4,038
NT$4,579 total
includes taxes & fees
Jul 23 - Jul 24
Osteria del Borgo
Il Palazzetto
Relax in this open-plan living area with a patio offering a serene view of lush green surroundings.

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto
Relais il Ciliegio
Stroll through the historic town square, surrounded by traditional stone buildings and a prominent clock tower.

Relais il Ciliegio

Relais il Ciliegio
Castello di Modanella
Stroll through the historic entrance, lined with lush greenery and soft lighting.

Castello di Modanella

7.6 out of 10, Good, (14)
"Property is closing and looks like it. Very unfortunate, I was there 30 years ago with fond memories! Obviously I should have done more homework!! Very sad."
Castello di Modanella
Podere La Chiusella
Relax by the pool surrounded by lounge chairs and umbrellas in a serene outdoor space.

Podere La Chiusella

9.4 out of 10, Exceptional, (30)
Podere La Chiusella
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

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"We had the most amazing stay at Castello di Velona. The staff was top notch. The facilities are breathtaking. "
Lacey 3-night trip
Posted 2 days ago
Castello di Velona Resort Thermal SPA & Winery

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.

How many vacation rentals are there in Pienza?

Expedia has 29 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 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.