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Top Holiday Rentals in Pienza

A cozy nest for a pair
Aerial view
A cozy nest for a pair
10.0 out of 10, Exceptional, (1)
"Visite de Florence et Sienne"
A cozy nest for a pair
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
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Magnificent stone farmhouse in the heart of Tuscany
Exterior
Magnificent stone farmhouse in the heart of Tuscany
10.0 out of 10, Exceptional, (23)
"My son and I had a wonderful stay at this property in March. The villa was really well equipped, with all amenities, and had a huge amount of land around it. Everything was really well cleaned. The sheets were comfortable and pristine. We appreciated the large white towels and extra blankets. The heaters worked really well as did the chimney. The views were superb and we were surprised with wildlife including the deers. Franco guided us well and was a pleasure. He pointed us to great experiences...
Magnificent stone farmhouse in the heart of Tuscany
Il Tosco
Property entrance
Il Tosco
10.0 out of 10, Exceptional, (86)
"Il Tosco is a quiet, clean and charming place to stay while traveling in Tuscany. The common rooms are cozy and the elegant breakfasts are the best we encountered in Italy. This is a wonderful place to stay with a local quality. Well worth the higher cost. "
The price is £255
includes taxes & fees
9 May - 10 May
Il Tosco
wrapped in the scent of Mediterranean flowers and herbs
Exterior
wrapped in the scent of Mediterranean flowers and herbs
10.0 out of 10, Exceptional, (42)
"Casa Cadeta provided a peaceful and beautiful rural home base for our Tuscany tour. We chose to make breakfasts and dinners in the fully equipped kitchen and make daily tours to hilltop Medieval villages, beaches, or wine tastings. At nights we enjoyed star gazing and listening to an owl and the neighbor’s donkeys. Laine was generous in sharing garden and orchard bounty and we enjoyed organic tomatoes, figs, grapes, almonds, and apples. Would love to come back!"
wrapped in the scent of Mediterranean flowers and herbs
Tuscan stone villa with private pool surrounded by greenery
Outdoor pool
Tuscan stone villa with private pool surrounded by greenery
10.0 out of 10, Exceptional, (82)
"My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa...
Tuscan stone villa with private pool surrounded by greenery
Delcorto Suites
Interior
Delcorto Suites
10.0 out of 10, Exceptional, (11)
"Everything is great. The family owns the property over 600 years. Great breakfast, fabulous suite. "
The price is £141
includes taxes & fees
14 May - 15 May
Delcorto Suites
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
A heated pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (37)
"Three generations of our family spent two weeks at this beautiful villa, and it was a very special vacation. The villa, grounds and pool are maintained in perfect condition - just the right combination of old-world charm with modern conveniences. The kids loved the pool, and the adults very much enjoyed the cocktail hour in the beautiful grounds by the pool at the end of the day. We love to cook, as a family, and found everything we needed to prepare meals in the huge kitchen. We also had...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Cottage " I due Pini"
Exterior
Cottage " I due Pini"
10.0 out of 10, Exceptional, (35)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
Il Poggio dell'Eremita
Interior
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (37)
"The host was very welcoming upon arrival and gave us a great tour of the property along with some area history. Such a peaceful setting. Really enjoyed the patio upstairs off the bedroom. Great views of the terrain by day and fantastic views of the stars at night. Very close to the enchanting villages on hilltops nearby (Rigamagno and Scrofiano)."
Il Poggio dell'Eremita
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
Exterior
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
10.0 out of 10, Exceptional, (188)
"Wonderful house and wonderful hosts. Stayed over Easter and would love to come back during summertime."
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (53)
"Quaint, comfortable apartment with spectacular views from patio. Easy walking distance to main square. Alen, the property manager who checked us in was great; a Cortona resident who provided lots of suggestions. Samantha, the owner was also easy to work with and stayed in communication from booking to departure. Highly recommend property and host. For those arriving by train, I would suggest booking a taxi well in advance as they are difficult to arrange. We booked Saban Salijevic who was great!...
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Outdoor pool
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
9.8 out of 10, Exceptional, (90)
"We had the most amazing time at Il Poggio! The property is well maintained, Roberta and Marina were incredible, and the location could not be beat. We took day trips (by car) to Siena, Arezzo, Florence, Orvieto, and Montalcino, all of which were easily and quickly accessible. Each of our five guests (two couples, one single!) had their own floor and bathroom. We cooked in the well-stocked kitchen, drank wine while watching the sunrise on the patio, and were transported to the past walking...
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Idyllic location, peaceful aromatic garden for absolute relaxation & tranquility
Exterior
Idyllic location, peaceful aromatic garden for absolute relaxation & tranquility
9.8 out of 10, Exceptional, (42)
"Very loverly place to stay. A few km down a gravel road but that adds to the experience. Graham is a gracious host. He provided lots of info places to visit and shopping."
Idyllic location, peaceful aromatic garden for absolute relaxation & tranquility
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Pool | Outdoor pool
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
9.6 out of 10, Exceptional, (38)
"The house is a beautiful old Italian house with high ceilings with wooden beams and tiled floors. Everything in the house worked pedfectly- wifi, hot water, screens on the windows, kitchen and bath. The house is set in the midst of the Tuscan hills with hikes starting right from the front door. The grounds in the nature preserve are lovely with local plantings. The hostess, Marina, was welcoming, helpful, and altogether delightful. The gravel access road is steep and curvy in places. We were...
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
House in Val d'Orcia excellent for families ISTAT code Tuscany region: 052024LTN0004
Exterior
House in Val d'Orcia excellent for families ISTAT code Tuscany region: 052024LTN0004
9.6 out of 10, Exceptional, (36)
"Beautiful home and location. Silvano is excellent host."
House in Val d'Orcia excellent for families ISTAT code Tuscany region: 052024LTN0004
Ancient Tuscan house in the medieval village of Castiglione d'Orcia
Property grounds
Ancient Tuscan house in the medieval village of Castiglione d'Orcia
9.6 out of 10, Exceptional, (14)
"Lovely spot to be in the middle of this lovely village."
Ancient Tuscan house in the medieval village of Castiglione d'Orcia
Bosco della Spina
Exterior
Bosco della Spina
9.4 out of 10, Exceptional, (122)
"Charming property in midst of magical Tuscany."
The price is £71
includes taxes & fees
13 May - 14 May
Bosco della Spina
A private luxury retreat in Montalcino
Pool
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (47)
"We loved this place. Beautiful pool, facilities and views"
A private luxury retreat in Montalcino
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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.

Pienza Holiday Rental Travel Info

Number of holiday rentals
136
Popular accommodation
Pienza villas
Known landmarks
Terme di Montepulciano Spa, Pienza Cathedral and Piscine Termali Theia
International airports
Rome (FCO-Fiumicino - Leonardo da Vinci Intl.), Rome (CIA-Ciampino) and Florence (FLR-Peretola)

Other types of properties in Pienza you may be interested in

Tenuta Santo Pietro
Exclusive Villa, 2 Bedrooms, Garden View, Annex Building | Terrace/patio
Tenuta Santo Pietro
9.6 out of 10, Exceptional, (83)
"Lovely, comfortable farmhouse style. Beautiful views and several offerings like cooking classes. Staff welcoming and helpful. Farm to table meals were excellent with many local options to choose from. Manager, Bertina, is a gift, making sure all guests were happy and carrying out her duties with care and great energy and coordination. Bravo! "
The price is £148
includes taxes & fees
2 Jun - 3 Jun
Tenuta Santo Pietro
Hotel San Gregorio
Seasonal outdoor pool, pool loungers
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (98)
"Very nice staff, great service, super clean. Will stay again."
The price is £151
includes taxes & fees
14 May - 15 May
Hotel San Gregorio
Hotel Corsignano
Land view from property
Hotel Corsignano
4.0 star property
9.2 out of 10, Wonderful, (239)
"Considering that the hotel is in a small town in Tuscany, it provides all modern amenities. It is in the center of the village close to dining, shopping, and amazing views."
The price is £163
includes taxes & fees
20 May - 21 May
Hotel Corsignano
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.

Everything you need to know about Pienza holiday rentals

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

Pienza holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza holiday rentals we have selected for you start as low as £71 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Pienza?

Yes, there are holiday rentals in Pienza close to RI Crea RE, or you can select a more secluded option if you're looking for 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 holiday rentals that Pienza has to offer?

Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista: This holiday home rental outside of Pienza is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Pienza?

Expedia has 27 holiday 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 holiday rental in Pienza like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pienza. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.

Recent reviews of Pienza properties
Expedia verified reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5/5 Excellent
A wonderful hotel
"This is a wonderful hotel in every way: a beautiful building in an amazing location; excellent food at breakfast and dinner; a lovely, comfortable room and, most importantly, kind, welcoming and helpful staff. "
A verified traveller stayed at Monastero di Cortona Hotel & Spa
Posted 4 days ago
Monastero di Cortona Hotel & Spa