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House holiday rentals in Piancastagnaio

Find and book unique houses on Airbnb

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Popular amenities for Piancastagnaio house rentals

House rentals with a pool

Guest favourite
Home in Arezzo
4.9 out of 5 average rating, 166 reviews

Italian Interior

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Guest favourite
Home in Asciano
4.97 out of 5 average rating, 33 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars1 week ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Top Guest favourite
Home in Orvieto
4.96 out of 5 average rating, 72 reviews

The romantic "Bennicelli Tower Suite"

RoeiRating, 5 stars1 month ago
We had a wonderful time staying with Andrea. He was very welcoming and always available to help. He assisted us with great recommendations and with booking restaurants and wineries. The tower itself is a truly unique place, and the peaceful surroundings created the perfect atmosphere for our stay.
Superhost
Home in Pievescola
4.93 out of 5 average rating, 106 reviews

Antico Borgo Ripostena – n. 9 Oil Mill

DanielRating, 5 stars2 weeks ago
Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.
Top Guest favourite
Home in Cetona
5 out of 5 average rating, 78 reviews

Il nido del Rondone

EveRating, 5 stars3 weeks ago
You will not regret your stay! From the moment we were greeted by Elisa’s father on arrival we felt welcomed. The accomodation exceeded our expectations with absolutely everything that you would need with the bonus of being able to access to the amazing pool. It is only a short walk down to the city centre. To top this all off, the hosts are extremely generous and friendly. Thank you for sharing your little piece of paradise with us. We will look at returning one day!
Top Guest favourite
Home in Pereta
5 out of 5 average rating, 56 reviews

Bel Casale with sea view and the mediaeval village

AmarRating, 5 stars1 week ago
Staying at Paola and Nino’s place was one of the highlights of our trip. The house is even more beautiful than the photos, with every detail thoughtfully considered and a setting that truly captures the essence of Tuscan magic. It’s incredibly peaceful, with sweeping views and a real sense of privacy, yet close enough to explore charming villages and beaches. The house is well-equipped and very comfortable, with excellent air conditioning in the bedrooms, a real plus during the summer heat. Paola and Nino were the most gracious hosts, warm, welcoming, and always available if we needed anything, yet also giving us plenty of space. Their three sweet labradors were a lovely bonus! We truly didn’t want to leave and would return in a heartbeat.
Superhost
Home in Lucignano
4.85 out of 5 average rating, 39 reviews

La Casetta

LauraRating, 5 stars1 month ago
Beautiful, peaceful stay. Amazing, secluded location. The hosts were very friendly and welcoming - made us feel right at home. Lots of great walks around, including the nearby winery. The only downside is it does get rather cold in the stone apartment but during warmer weather the coolness in the apartment would probably be perfect. They provided a portable heater & a hot water bottle though which was nice. Thank you Tebea for being such a lovely host!
Top Guest favourite
Home in San Feliciano
4.9 out of 5 average rating, 143 reviews

Casa dei 5 Sensi - Trasimeno view

RobertoRating, 5 stars3 weeks ago
What a beautiful place! Great view of the lake. Sergio was incredibly friendly and responsive. He gave us local recommendations and even made us a fruit salad. I will definitely be booking with Sergio again the next time we are in Umbria.

Weekly house rentals

Superhost
Home in Castell'Azzara
4.75 out of 5 average rating, 4 reviews

Entire accommodation. Historic house La Dimora nel Borgo.

EleonoraRating, 5 stars1 month ago
The house is really beautiful, spacious and well-stocked, great for group trips! The village is easily accessible by car and is super quiet and immersed in the Tuscan hills.
Guest favourite
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars2 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Top Guest favourite
Home in Città della Pieve
4.97 out of 5 average rating, 76 reviews

The Terrace of Victory

MagnusRating, 5 stars1 day ago
Alessandro is a very nice and thoughtful host. The place and the view is great. It has everything you need for your trip (probably best for couples or on your own). Having a car is almost non negotiable but that also makes it very calm and quiet. Groceries and some great ice cream are close by. Can only recommend!
Top Guest favourite
Home in Monticchiello
5 out of 5 average rating, 39 reviews

Lovely home to dream

NadinRating, 5 stars2 weeks ago
Sarah was in touch with us before arrival, recommended restaurants and inform us about the parking place, as you can't park inside the old town. the apartment was as in the pictures, beautiful view
Top Guest favourite
Home in Pitigliano
4.98 out of 5 average rating, 45 reviews

CasAgata

IrynaRating, 5 stars1 week ago
Our stay in Pitigliano was incredible! Check-in was super easy, and the host was extremely responsive and helpful—guiding us with parking, luggage, and making sure we felt right at home. They even recommended the BEST restaurant in town! After two weeks in Italy, I can confidently say this charming city had the best service, most welcoming staff, and hands down the most delicious food—those sausages were unforgettable! There was a bit of noise in the master bedroom since the wall connects to the restaurant next door, but thankfully the apartment had a second bedroom where we could place our light-sleeping toddler, and it worked out perfectly. Pitigliano is such a unique gem, and our stay made it even more memorable. Highly recommend!
Guest favourite
Home in Contignano
4.95 out of 5 average rating, 19 reviews

Noi 2 Vacanze in Fortino d 'Amore

MikeRating, 5 stars1 month ago
This was a wonderful space with amazing history of the Val d'Orcia. Giuseppe was a delight showing us everything we needed to know in this very well appointed two story unit. The bed was extremely comfortable and the hosts went to great lengths to supply everything we could need, especially the Illy coffee and moka pot for espresso. Having the clothes washer was a big plus. The views from every window are breathtaking and the location is a perfect balance of feeling out in the country while close to tourism sites. Have a car was very useful. The unit sits amongst many making it feel like a little quaint and quiet town with a small grocery steps away. We were very fortunate to have found this place and would recommend to anyone as something very special and quietly romantic.
Top Guest favourite
Home in Pienza
5 out of 5 average rating, 53 reviews

Pienza Center - Stylish Apt, 6 Guests, A/C & WiFi

ShirleyRating, 5 stars2 weeks ago
We loved our stay in this apartment. It was perfect for the three of us - clean and very well stocked for us with extra amenities!!!! We really appreciated that. We love Pienza, and very much enjoyed our stay here. Thank you!!!
Guest favourite
Home in Sasso D'ombrone
5 out of 5 average rating, 29 reviews

Tosco Suite "Solis"

DinaRating, 5 stars2 days ago
Location was perfect and close to fun things to do. The host was very responsive and friendly. 10/10 recommend staying here. Everything was very cleaned and beautiful.

Private house rentals

Guest favourite
Home in Monticchiello
5 out of 5 average rating, 19 reviews

"Villa Emma" Guest House with Garden

KateRating, 5 stars1 month ago
We had a nice stay at Villa Emma. The bed was comfortable, the kitchen well-stocked, and the patio was perfect for enjoying the beautiful weather. The apartment is close to a playground, shop, restaurants, and a quick drive to farms and surrounding towns. Deborah provided a crib for our baby and her restaurant had high chairs, which we really appreciated. The included breakfast at her lovely restaurant was delicious and convenient. She also left a welcome bottle of prosecco for us in the apartment. When we had car trouble, she quickly found a mechanic to look at our car. She was very responsive and helpful and made it a wonderful trip to Tuscany!
Superhost
Home in Bagnolo
4.64 out of 5 average rating, 14 reviews

Mountain house with outdoor space

CarmelitaRating, 5 stars1 month ago
Cozy place, the decor of the house cared for in every detail, a mountain house feels like a dip in the past. Ida provided all the information in a clear, detailed and accurate way, she recommended us to see the village of Santa Fiora (wonderful! to visit) a few kilometers from Bagnolo. I recommend it to those who love quiet places in contact with nature.
Top Guest favourite
Home in Campiglia D'orcia
5 out of 5 average rating, 22 reviews

Casa Letizia: Val d'Orcia, Thermal Baths and Mount Amiata

FilipaRating, 5 stars1 month ago
Our family had a wonderful stay at Letizia’s accommodation. The beauty of the home and surrounding valley exceeded the photos and description. We felt so welcome and at home and had plenty to do from walking on the farm to visiting the many surrounding towns. Letizia recommended a local restaurant which was superb. Letizia helped us immensely with any question we had and it was a big highlight of our trip to Europe. Thank you Letizia!
Top Guest favourite
Home in Torrita di Siena
4.98 out of 5 average rating, 46 reviews

Casa Ilda A/C, Wi-Fi Private parking

NicolasRating, 5 stars1 week ago
Great place! Beautiful area and close to the activities we had planned. Very clean and spacious apartment - clear instructions.
Top Guest favourite
Home in Cortona (Pierle)
4.98 out of 5 average rating, 51 reviews

"L'Antico Metato" house in the woods

FriederikeRating, 5 stars3 weeks ago
We were there for 4 days and it was simply fantastic. The arrival was smooth and Flavia welcomed us very warmly on site. After a short tour of the house and a short briefing, the holiday could begin. A note with restaurant recommendations and excursion destinations was ready on the table. After a short thunderstorm, we had a power outage, but Flavia was immediately available and within 5 minutes we had power again. Shopping and restaurants are easily accessible by car. I can recommend this accommodation to anyone who longs for peace and wants to enjoy nature. We will be happy to come back!
Guest favourite
Home in Montalcino
4.94 out of 5 average rating, 32 reviews

Domus Antiqua

JonathanRating, 5 stars5 months ago
We had an excellent stay at this beautiful home which is very spacious, comfortable and very well furnished. The views are superb even by the high standards of Montalcino. Communication was proactive and very helpful. Nothing to fault. We would definitely stay again and look forward to doing so.
Superhost
Home in Seggiano
4.79 out of 5 average rating, 28 reviews

Panoramic view with mountain view of old Norman house

ChristineRating, 5 stars1 month ago
Those who love the tranquility and the ideal starting point for visits in the area plus a lovingly furnished home will be right with Federico. Both cafes in the village are beautiful places to stop in the evening, enjoy the view from the mountain to the fantastic countryside. Seggiano is located on a stop, the house in the middle of the village. We made many fantastic excursions and were always happy to return to Seggiano in the evening and experience this special place. Thank you for your hospitality!
Top Guest favourite
Home in Tuoro sul Trasimeno
5 out of 5 average rating, 53 reviews

the oasis of the foxes

AbbyRating, 5 stars1 week ago
Beautiful home in a more secluded area overlooking Lake Trasimeno. The trains and a highway are below but not invasive. The views are beautiful. The home was clean and tastefully updated but still clearly old and had a lot of character. We did not have a car and the train station is an hour walk away. There are a couple buses that pass through but not enough to be a reliable means of getting to and from the house. Even the taxi was busy and we had to be flexible on when we went to the train station but it worked out fine. We walked to and from Tuoro for groceries and visited La Puntabella for a great dinner with a view. It was an adventure and we enjoyed it despite our plan not being very good for this location. Sonia was patient and helpful in working out our means of travel and figuring out the bus schedule. Natolino reminded us of home and he is fun to watch and listen to.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Piancastagnaio
  6. House rentals