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House vacation rentals in Pieve Santo Stefano

Find and book unique houses on Airbnb

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Popular amenities for Pieve Santo Stefano house rentals

House rentals with a pool

Guest favorite
Home in Loro Ciuffenna
4.92 out of 5 average rating, 39 reviews

"Tuscany Villa with PRIVATE pool"

LeonardoRating, 5 stars3 months ago
I recently stayed at this amazing Airbnb and couldn’t have been happier with the experience. The hosts were absolutely fantastic—kind, attentive, and incredibly helpful. They went above and beyond to ensure my stay was perfect, even recommending a stunning restaurant that became the highlight of my trip. The accommodation itself was spotless, cozy, and perfectly located, making it easy to explore the area. I truly felt at home and can’t wait to return. Highly recommend staying here if you’re looking for a memorable experience! Five stars all the way!
Guest favorite
Home in Fiesole
4.97 out of 5 average rating, 30 reviews

Scenic country house with large pool near Florence

YvonneRating, 5 stars7 months ago
Michael greeted us on arrival and was extremely welcoming and took time to show us around his beautiful home. This was a family holiday with 6 adults and the ample space both inside and out worked perfectly for us all, we felt at home and relaxed. The whole house is extremely luxuriously and well equipped, we used the BBQ and the pizza oven both of which worked perfectly. Michael was always available to help with any questions we had and the location is perfect for day trips to Firenze, Siena etc. We enjoyed a wonderful week and would thoroughly recommend Michael’s home.
Superhost
Home in Reggello
4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars7 months ago
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!
Top guest favorite
Home in Reggello
5 out of 5 average rating, 44 reviews

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.

MicheleRating, 5 stars1 week ago
Very nice place to stay in the hills of Tuscany. A little remote but we appreciated that. Many restaurants nearby with really very good food and absolutely good prices. Accommodation with large garden, pool, air conditioning and heating. Well-kept and clean. Chickens whose eggs we were allowed to collect. Magena was always available, very friendly and helpful. Many wineries in the area where you can eat and drink. We will be back. Thanks Magena and Eduardo
Top guest favorite
Home in Pergaccio
5 out of 5 average rating, 46 reviews

Villa Pergo is an ancient charming country villa

TerriRating, 5 stars6 months ago
Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi
Top guest favorite
Home in Serre di Rapolano
4.97 out of 5 average rating, 74 reviews

L'Olivo - detached villa with swimming pool

MartaRating, 5 stars7 months ago
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.
Guest favorite
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars7 months ago
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!
Guest favorite
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", house with swimming pool at the foot of Cortona

AlessandroRating, 5 stars4 months ago
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.

Weekly house rentals

Guest favorite
Home in Figline e Incisa Valdarno
4.91 out of 5 average rating, 44 reviews

POMEGRANATE CAMPOPINETA

AmandaRating, 5 stars6 months ago
Alessandra’s place was an absolute dream. It’s picturesque with the most gorgeous view of Tuscany hills in a rustic styled rental. She was extremely helpful and attentive during our stay! Would definitely come back here next time we visit!
Superhost
Home in Lucignano
4.78 out of 5 average rating, 9 reviews

Beautiful property between Siena and Arezzo

TimRating, 5 stars20 months ago
we had a very nice stay. The entire accommodation was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.
Superhost
Home in Ville
4.79 out of 5 average rating, 29 reviews

Independent Tuscan Villa Siena with Pool (7+1)

RonRating, 5 stars7 months ago
We stayed for a week and had a wonderful time. The house is well maintained and exactly as per the description provided. Giovanna and her family are highly responsive and responded instantly to any queries we had. We would highly recommend anyone wanting to go to the Toscana to stay at this wonderful house.
Top guest favorite
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 82 reviews

Villa close to Florence amazing view private pool

Ane ElineRating, 5 stars7 months ago
Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!
Guest favorite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars5 days ago
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again
Guest favorite
Home in Arezzo
4.91 out of 5 average rating, 86 reviews

La Casa di Daniele&Patrizia-Family, relax and view

LisaRating, 5 stars6 months ago
The views from this guest suite will be some of my favorite memories of Tuscany. I highly recommend going outside 30 minutes before sunrise to watch the sky change colors against the mountains while you take a deep calming breath looking across the valley below. The guest house is compact, modern, and clean. And Patrizia and her family are just next door, available and friendly if you need anything.
Superhost
Home in Lisciano Niccone
4.69 out of 5 average rating, 49 reviews

Casa Trasimonte | country house with private pool

CarinaRating, 5 stars9 months ago
We had an amazing week in Casa Trasimonte, where we enjoyed the house, the pool, the terrace and the view. The house is richly equipped, so we ate a lot at home. We also ate at the local restaurant Lo Scoliotto, where the view and food are good. In Tuoro, we ate with great views of the lake. Largo Trasimeno itself was a bit of a disappointment. Not to look at (really beautiful), but not inviting to bathe. We did great walks in the mountains around the house and met a beautiful animal diversity. All in all, a great recommendation from us.
Superhost
Home in Rietine
4.85 out of 5 average rating, 206 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars5 months ago
What a great getaway!! We hope to make it back soon!

Private house rentals

Guest favorite
Home in Radda in Chianti
4.85 out of 5 average rating, 177 reviews

Tuscany House "La Querce Sola"

EricRating, 5 stars1 week ago
Rosanna and her country house are as great as all the reviews say. The house is spacious, comfortable, clean, quiet, charming with beautiful views of the surrounding hills. Great place to relax with family. If you intend to use the oven ask for instructions, it works fine but the operation wasn’t intuitive for us. Also bring plenty of bottled water, the house supply is fine for washing but not for drinking/cooking. Rosanna gave us great recommendations for dining and sightseeing in the Radda/ Castellina area, great place at a reasonable rate!
Home in Monte San Savino
5 out of 5 average rating, 5 reviews

La Salciaia by Interhome

DavidRating, 5 stars9 months ago
We had a great stay with friends and family! The house is big, the garden is superb (and large!) and the swimming pool was big and safe. The owners were also very reactive to our requests, and the chef option is highly recommended for at least part of the stay! Thanks again, and see you again soon.
Superhost
Home in Foiano della Chiana
4.87 out of 5 average rating, 31 reviews

Casa Walter Valdichiana

OrrRating, 5 stars2 weeks ago
We had a wonderful stay at Julia's villa in Tuscany! The home was beautiful, spotless, and perfectly hosted — Julia made us feel truly welcome. The surroundings were stunning and peaceful, the perfect Tuscan experience. Highly recommend!
Home in Radda in Chianti
5 out of 5 average rating, 9 reviews

Le Bonatte by Interhome

CarlRating, 5 stars7 months ago
Joy (the owner) is a joy! She is one of the best hosts we’ve had on this platform. Flexible checking, due to delayed flight. Rooms were bigger than anticipated and beautiful. Lovely rustic Tuscan charm of a property. Plenary of recommendations at the property for local restaurants and activities. Can’t recommend this property enough!
Home in Pergine Valdarno
5 out of 5 average rating, 8 reviews

Pianelli by Interhome

DiegoRating, 5 stars22 months ago
The stay was amazing, the Host Luciano was very nice and forthcoming about any inquiry we had. I can recommend the place to anybody who wants to have a nice, chill time in the hills of central Tuscany.
Home in Cortona
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

ChristophRating, 5 stars7 months ago
The terrace was great, and the entire place had a quiet and peaceful feeling.
Top guest favorite
Home in Castiglion Fiorentino
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars5 months ago
It was an absolute delight to stay at this gem of a property. We booked for 10 days and had a chance to enjoy and explore the surrounding areas. The house is spotless, comfortable, spacious, and fully equipped with modern appliances. So it has exceeded our expectations and would love to book it again in the future. Our host Alberto, is welcoming and very friendly, making the process of checking in and out quite seamless. My overall impression is 10/10.
Guest favorite
Home in Civitella Val di Chiana AR
5 out of 5 average rating, 17 reviews

Il Giglio Farmhouse by Interhome

Maria AlejandraRating, 5 stars1 week ago
Casale Il Giglio is a beautiful place and hosts Silvia, Gianlucca and Neri make the experience even better; they are thoughtful and kind and made our family of 4 feel right at home. It is just like the photos, if not better. It was a highlight on our trip and we hope we can go back!

Destinations to explore