Pienza is one of the most beautiful cities in all of Tuscany. Located not far from Siena, this UNESCO World Heritage Site is enchanting, to say the least. Culture and history lovers will love visiting Duomo Di Pienza and wandering the gorgeous cobblestoned streets. Foodies, especially oenophiles, will have a ball trying pecorino, drinking wine at the many vineyards, and visiting local farms for lunch. However, one experience everyone must try is staying at a Tuscan villa. After all, what could be a more magical experience than staying at a pretty vine-and-blossoms-covered structure which is hundreds of years old? Vacation rentals that are vintage on the outside but modern on the inside make for a great base in Pienza. To that end, here are the best Airbnb vacation rentals in Pienza, Italy.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Lovely home with a garden (from USD 145)
A feeling of cosy comfort and warmth will envelop you as you step into this ground-floor apartment. Featuring a lovely walled garden and a huge red door entrance, the place opens onto a living room-cum-kitchen that’s perfect for making meals and enjoying them.
The small porch is the perfect way to begin and end your day with your cup of coffee or glass of wine. If you’re here during the winter season, the wood-burning fireplace is perfect for warming up. Summers are best spent at the outdoor table, digging into great Italian fare.
Top guest reviews
Amenities & Room:
there is air conditioning that worked well and the beds were comfortablethe apartment is a true two bedroom with lots of space and was perfect for our family of threekitchen is well equipped and there is a small yard that is pleasant to have meals in tooit was especially nice to have a washer that was easy to use hot water and wifiit could easily accommodate more with the extra bed in the master and double/queen in the 2nd bedroomCleanliness:
the house was exceptionally clean you could smell the freshness in the airthe place is clean and artistically designed and decoratedthe space was a pictured and very comfortable and cleanvaleria's place has a lot of character the place was clean and nicely stockedthe house was clean and the position was 2 min walk from the city centerHost:
also host is very kindliga was very lovely and accommodatingthe hosts welcomed us into their lovely garden and shared fresh producevery friendly and helpful hostsbrilliant place and fantastic host - would recommendRead more reviewsLocation:
amazing location just a few strides away from the center of pienzathe location was perfect for walking to the townin a perfect location just a short walk in to pienza centrewas the perfect location for uscool space very close to center
2. Residenza di Nedo
For travellers who like to keep it quiet, this ground-floor one-bedroom home in a peaceful Pienza neighbourhood is just the ticket. Lying just a five-minute walk from the city centre, the house also has a lush garden where you can enjoy a stroll.
Begin your days with an offered breakfast of fresh fruit, biscuits, yoghurt, juices, and pastries, along with coffee from the espresso machine. A spacious and tastefully decorated bedroom with a king bed, a dining nook, and a kitchen/living area will make your stay all the more comfortable.
Pienza, Toscana, Italy
14.87 km (9.3 mi) from Abbazia di Monte Oliveto MaggioreSuperhost
Accommodates: 2
Top guest reviews
Amenities & Room:
warm and cozy within steps of an amazing vista of val d’orciahe had left us a huge amount of food on the table and in the frigeratercomfortable and generous space in apartment to relaxwe had a lovely stay at federico’s apartmentthe place is great with thoughtful touches such a breakfast food and essentials for cookingCleanliness:
the place is very clean and spaciousthe apartment was so clean and nicely furnishedthe space was clean comfortable quiet with parking right outsidesparkling clean and like having your own villa with lots of breakfast suppliesgreat host very clean and stylish home with very comfortable bedHost:
friendly and helpful hostnice place with nice hostfederico is a great host; he made everything to make us feel like at homegreat host indeed place was perfect and feel like homefrederico was an excellent hostRead more reviewsLocation:
easy walk in to town center with lovely restaurants to choose fromit was in a great location with a picturesque short walk into townlocation is the center of mini town like pienza at walkable distancepeaceful location and a short walk to town fabulous restaurants steps away from breathtaking viewsgreat location with best 5 min walk into town you’ll ever do
3. La Dimora di Arturo (from USD 64)
Lots of potted plants, natural light, and modern comforts make this historic Pienza centre apartment just perfect. Wrought iron beds with a plush mattress, a cosy dining nook, and a full kitchen will make your stay delightful. The icing on the cake is the courtyard garden, complete with wrought iron alfresco seating. It’s a great place to end the day sipping on wine and staring up at the stars.
Top guest reviews
Amenities & Room:
great stay at marco's apartmentthe flat is spatious with really well equipped kitchenCleanliness:
great clean place to stayplace was clean and marco was responsive to messagesit was a pleasant stay the apartment was clean and comfy and easy to findvery clean spacious apartment with a nice kitchen and pretty decoratingthe appartment was clean and had everything you needHost:
very kind and responsive host would highly recommend this apartment for a stay in pienzamarco is very helpful with local suggestionsit would be helpful if the guests can get parking place too but everything was perfectRead more reviewsLocation:
amazing location in the middle of pienzaperfect location a few steps away from short-term parkinggreat location and easy to findamazing location in one of the most beautiful settings ever surrounded bygreat place and very good location
4. Window of the Angel (from USD 90)
Feel like you’ve stepped back in time at this charming one-bedroom apartment set in an ancient period building. Tucked right in Pienza’s historic centre, this place is decked out in Tuscan rustic style. Think antique furniture, exposed beams and high ceilings. This old-fashioned style contrasts the home’s modern creature comforts, such as a fully equipped kitchenette with appliances for cooking.
Guests can relish meals while watching TV in the comfy living area. A cosy bedroom with a double bed, a contemporary bathroom and Wi-Fi make up the rest of the place.
Top guest reviews
Amenities & Room:
only wifi could have been bettervery beautiful room on a quiet side street in the old townHost:
very easy check-in/out even though the host marco speaks only a little englishRead more reviewsLocation:
comfortable warm due to a good functioning heating system with a central control panel (end of september 2019)marco’s apartment in pienza was a lovely and wholesome place to stay for our week trip away
5. The Tower of St. William (from USD 112)
How would you like to live in an ancient tower decked out with modern amenities with your significant other? Located a stone’s throw from the town’s centre, this one-bedroom place near the Tower of San Guglielmo is a relaxing and romantic stay. Besides breathtaking views of Val d ‘Orcia, it also offers oodles of privacy and tranquillity.
Packaged breakfast products, an equipped kitchen, and Wi-Fi ensure that you only need to step out when you want. Sipping on wine in the middle of the olive tree garden while relaxing in the shade is also a great way to pass the time on the property.
Top guest reviews
Amenities & Room:
we would have never left if it was possible the views from the bedroom and bathroom were stunningbreakfast consists of basic prepackaged items but there are good bakeries in towninterior is rustic and cozy - more charming than the picturesCleanliness:
very clean place with historic charm great views and lovely walk into the cityHost:
vania was very communicative and we appreciate her hospitalitythis place was truly one of a kindRead more reviewsLocation:
guglielmo is a unique experience the location is fantasticwe also enjoyed the close proximity to the beautiful pienza and strolling among the surrounding countrysidegorgeous 10-15 minute walk into townamazing romantic getaway walking distance to town yet still tucked away in the country with amazing viewsvania’s place was absolutely amazing it’s located in a quiet area just outside of town
6. Cosy one-bedroom apartment with terrace (from USD 75)
Couples who want to explore Pienza will love this city centre apartment that lies in a private courtyard. The house features a bedroom with a double bed which ensures you wake up reinvigorated the next day. Begin mornings with coffee from the kitchen and end your days making romantic meals.
Be sure to take advantage of the mountain bikes available for guest use to explore the town. After a long day, you can relax with a glass of wine on the terrace.
Top guest reviews
Amenities & Room:
cozy apartment with a nice balcony and view of tuscanythe room has ac which really helps on hot nightseverything was clean very well stocked with coffee sugar toilet paper shampoo and soapthe bed was comfortable the shower was great and the furniture was quite nicewe loved the balcony and his home is super cozy and lovelyCleanliness:
house itself is clean comfortable and spaciouscommunication was speedy flat was clean and bed is comfy what more could one need?place was clean and spacious and had everything we neededandrea’s apartment was clean nice and cozeythe flat was fully equipped clean and comfyHost:
andrea is an excellent hostandrea a great hostandrea was a very helpful and responsive hostandrea and helena were the best hosts any traveller could wantandrea is a perfect host friendly and helpfulRead more reviewsLocation:
great location and comfortable apartmenta great apartment in prime locationthe apartment is in a great locationit was a walk to parking but it wasn't too inconvenientthe stay was lovely a few steps to the old town perfect location
7. Modern vacation rental in Via del Bacio (from USD 83)
Nestled on one of Pienza’s most charming streets, this modern one-bedroom rental unit sits in an ancient-looking building, adding to its charm. The bedroom has a king bed, while the sofa bed can be pulled out in case there are more than two people staying. Apart from a modish bathroom, there’s also a kitchenette for whipping up quick meals, especially when you don’t feel like stepping out to dine. Finally, a TV and Wi-Fi take care of the entertainment front.
Top guest reviews
Amenities & Room:
living room with kitchen was perfect for my stayCleanliness:
also the place was very clean and the kitchen was small but very efficientHost:
alessandro is an amazing host & will do everything to make your stay as pleasant as possibleRead more reviewsLocation:
in short we had a fantastic stay at alessandro's place
8. L'Artistica Apartment (from USD 108)
Located on the second floor of a structure in the historic centre of Pienza, this apartment is perfect for creative travellers who love views. That’s because this place offers breathtaking views of the town and the Tuscan countryside beyond.
The spacious living room with a cushy sofa and a fireplace is the perfect place to relax at the end of the day. Cook meals in the full kitchen and watch TV as you relish your homemade Italian fare. Finally, two double and two single beds can accommodate up to five people.
Top guest reviews
Amenities & Room:
a beautiful old apartment with a spectacular view of the val d'orciathe aircon in the living room is great thoughgorgeous view comfy bed beautiful houseabove all the views from the kitchen window were breathtakingbreathtaking view from the apartment during daylight timeCleanliness:
this is a lovely apartment authentically tuscan clean spacious and extremely cozythe apartment itself was clean very tastefully furnished in a rustic tuscan style and comfortablevery clean centrally located apartmentthe apartment was spacious and the beds were comfortableHost:
host is great to communicate with though he doesn't live nearbythe host did take some time to respond even though he accepted our deposited well beforea very communicative and helpful host made our stay a memorable onegiuilio very helpful even made restaurant reservations for uswe appreciated the owner's friends helping us find the place in the dark of the eveningRead more reviewsLocation:
very close to tourist attractionsvery nice location and spaceperfect location if you’re a photographerthere are many places of interest conveniently close to pienzacharming spot in a fantastic location
9. Small and charming house in Pienza
Original stone arches, exposed beamed ceilings and vintage chandeliers are what add character to this gorgeous two-bedroom Pienza home. Located in a quiet corner of Pienza, this is a home for history enthusiasts. The place opens to a cosy living room, with a well-equipped kitchen to the side. The hosts also provide espresso and tea.
Up a flight of stairs is the second level, where lie the bedrooms - the main with a king bed and the other with a single bed. This home can accommodate up to four travellers, with one sleeping on the comfy sofa. Finally, the chic bathroom with heated floor tiles and a huge shower is a real perk, especially for those who like to take their time grooming themselves.
Pienza, Toscana, Italy
15.63 km (9.8 mi) from Abbazia di Monte Oliveto MaggioreAccommodates: 3
Top guest reviews
Amenities & Room:
wifi worked great toothe air conditioning in the bedroom worked effectivelythe house was very spacious and the wifi was very goodthe wifi was good - for example we could watch youtube videosi could get up early have coffee and breakfast without disturbing my wife’s sleepCleanliness:
exceptionally clean and very well equippedapartment was clean and had everything that we neededand the house was spotlessly cleanthe apartment was super clean spacious and well-furnishedit was very pleasant very nicely decorated quiet clean updatedHost:
they were lovely hostsgloria & antonio were the best hostsgloria and antonio were amazing hostsgloria and antonio were wonderful hoststhey were the most helpful hosts we have had using airbnbRead more reviewsLocation:
the location was perfect - close to everything but not in the middle of itvery well located in the centre of pienza on a cute streetgreat location everything was as advertisedeasy walk to everywhere in the citygloria's place was the perfect location
10. The Cedar House
While exploring Pienza, stay in the wonderful two-bedroom Cedar House, which lies a hop, skip, and a jump away from the city centre. The ground-floor home even has a large garden where you can enjoy walks or indulge in a session of yoga or exercise.
The large living area with a TV and the well-equipped kitchen is where all the action takes place. The kitchen has every modern appliance you’ll need, along with fresh fruit, biscuits, yoghurt, juices, and pastries for breakfast. A lovely dining room and spacious bedrooms, both with double beds, complete the place.
Pienza pienza, Toscana, Italy
14.79 km (9.2 mi) from Abbazia di Monte Oliveto MaggioreAccommodates: 4
Top guest reviews
Amenities & Room:
the wifi was nice and fastthe place had comfy beds a convenient location and better amenities than mostfederico was super helpful and even provided a basic breakfast which came very handyit stayed nice and cool inside - and we had fans and screens on the bedroom windowstwo big bedrooms made our stay very comfortableCleanliness:
the house is very clean and warmthe house is very spacious and clean toothe place is fantastic and very cleanthe house was very homely and clean with an excellent locationfederico was a great host the apartment was clean and spacious and in a great locationHost:
the host is very friendly and helpfulbeautiful place and super nice hostfederico was really kind and good hostfederico is very kind and responsive to our questions and requestsfederico was a great host greeting us at the apartment’s doorstep helping us with directions recommendations etcRead more reviewsLocation:
the location is greatgreat location in a very charming towna wonderful place quite close to pienzaw gentle walk all wayslocation is perfect for a visit to pienza or montepulciano
Make the most of phenomenal Pienza
The Tuscan city of Pienza is one place that cultural and history enthusiasts will love exploring. What’s special about Pienza’s vacation rentals is that many lie in ancient structures in the historic centre, allowing you to get a real taste of history while furnished in the most modern way possible. So, choose one of these best Airbnb vacation rentals in Pienza, Italy, for a memorable Tuscan vacation.
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