Pienza Vacation Rentals

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Vacation Rentals in Pienza

Il Tosco
10.0 out of 10, Exceptional, (87)
"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 CA $426
CA $475 total
includes taxes & fees
May 26 - May 27
Il Tosco
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
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
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Magnificent stone farmhouse in the heart of Tuscany
10.0 out of 10, Exceptional, (24)
"The property has beautiful views and a peaceful, remote location. It is well equipped for cooking meals and they conveniently provide a starter supply of necessities (kitchen spices, hand soap, laundry soap, toilet paper, etc.). The property owner, as well as the local property manager, were both very responsive to our questions and the check in and out processes are simple. We thoroughly enjoyed our stay."
Magnificent stone farmhouse in the heart of Tuscany
"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
wrapped in the scent of Mediterranean flowers and herbs
10.0 out of 10, Exceptional, (43)
"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
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 CA $279
CA $310 total
includes taxes & fees
Jun 5 - Jun 6
Delcorto Suites
Tuscan stone villa with private pool surrounded by greenery
10.0 out of 10, Exceptional, (83)
"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
The Gelda house, relax with a view
10.0 out of 10, Exceptional, (6)
"My wife and I loved this location. The view over the town and the proximity to the different towns was amazing. We would stay there again. The area is perfect for exploring."
The price is CA $147
CA $203 total
includes taxes & fees
May 14 - May 15
The Gelda house, relax with a view
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
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
10.0 out of 10, Exceptional, (30)
"Villa Mulinello is the perfect Tuscany Villa. It is located 5 minutes from the very quiet town of Montefollonico in a very private and beautiful setting. From the house and the yard on each side of the house you have a picture post card view of the valley of Montepulciano (vineyards orchards, woodlands) with an unobstructed view of Montepulicano. The house is large, comfortable and very clean. The Hosts are most gracious and helpful. You are close to all the Tuscany hilltop cites which you can...
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
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
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
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (54)
"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.
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
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
The House of Alice, charm and relaxation
9.6 out of 10, Exceptional, (42)
"This place was so pretty and away from the touristy areas. We were able to see San Giamigano (sp?). Siena, Montepulciano, Montalcino was very close by. This place is in the middle of the prettiest part of Tuscany!! The place was very nice but could use some racks or hooks for your towels and a place to put your shampoo etc. by the shower. 😁"
The price is CA $191
CA $259 total
includes taxes & fees
May 15 - May 16
The House of Alice, charm and relaxation
House in Val d'Orcia excellent 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 families ISTAT code Tuscany region: 052024LTN0004
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
Casanova - Panoramic Rooms and Suites
3.0 star property
9.4 out of 10, Exceptional, (18)
"The location is great, you have beautiful Tuscan view in front of yard. The room and bathroom are large, clean and modern with full kitchen. Good choice of breakfast, restaurant onsite is good for dinner. Free parking is good for travel by car."
The price is CA $239
CA $268 total
includes taxes & fees
May 29 - May 30
Casanova - Panoramic Rooms and Suites
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See all available properties in Pienza
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 Vacation Rental Travel Info

Other types of properties in Pienza you may be interested in

Podere Spedalone
1.0 star property
9.6 out of 10, Exceptional, (8)
"I LOVE this wonderful Agritourismo!! All the Staff made me feel at Home and beyond!! The location is Beautiful and Serene!! I will definitely return to this lovely Agritourismo if I travel to Italy again!!😊❤️❤️❤️❤️🇮🇹"
The price is CA $233
CA $259 total
includes taxes & fees
Jun 5 - Jun 6
Podere Spedalone
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 CA $248
CA $278 total
includes taxes & fees
May 20 - May 21
Hotel Corsignano
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 CA $284
CA $316 total
includes taxes & fees
May 24 - May 25
Hotel San Gregorio
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pienza. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista: 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. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Pienza?

Expedia has 27 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.

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