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House vacation rentals in Pienza

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Popular amenities for Pienza house rentals

House rentals with a pool

Guest favorite
A spacious outdoor pool is surrounded by lush greenery, featuring olive trees and vibrant plants. The pool's crystal-clear water reflects the sky, while a sun terrace with lounge chairs is available for relaxation. The serene landscape enhances the tranquil atmosphere of the setting.
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
Guest favorite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars3 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Guest favorite
A private pool is set within a well-kept garden, surrounded by lush greenery and gently sloping grass. The octagonal pool is framed by stone pathways and features a small tree at its center. The tranquil outdoor space invites relaxation and enjoyment.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Superhost
A charming stone farmhouse is set against a backdrop of green hills. The exterior showcases rustic features, including wooden shutters and a tiled roof. A pathway leads to the entrance, bordered by lush greenery and flowering plants, creating a serene environment.
Home in Figline Valdarno
4.96 out of 5 average rating, 108 reviews

The Owl: view, pool and garden

JasonRating, 5 stars4 weeks ago
What a great place to stay while visiting Tuscany. The home is a renovated medieval watchtower located up a dirt road, tucked on a hilltop overlooking the valley. Jacopo, the host, was so kind, hospitable and responsive during our 5-day visit. Would definitely recommend this place to explore Tuscana.
Top guest favorite
A charming stone house is situated beside a serene swimming pool, surrounded by lush greenery. Poolside sun loungers and umbrellas are positioned along the terracotta patio, offering a relaxing outdoor space. The clear blue sky and soft clouds enhance the tranquil atmosphere.
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)
Superhost
A stone pathway leads to a charming rustic building, surrounded by greenery and blooming flowers. To the side, a flat stone table under a large tree provides a serene outdoor space, inviting relaxation amidst nature.
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!
Top guest favorite
The outdoor pool features clear turquoise water, surrounded by a stone patio. Lush green hills and tall cypress trees create a scenic backdrop, while a few lounge chairs are positioned nearby for relaxation.
Home in Subbiano
4.99 out of 5 average rating, 84 reviews

Romantic cosy flat - Toscana Italy

BeckyRating, 5 stars3 days ago
This air B&B was in a beautiful area of Tuscany with breathtaking views. The property had many areas to sit and enjoy the rolling hills.

Weekly house rentals

Top guest favorite
The living area features exposed stone walls and wooden beams, creating a rustic ambiance. A spacious sectional sofa is complemented by a round accent chair. A round mirror reflects light from the window, while a decorative fireplace adds warmth to the space.
Home in Castiglion Fiorentino
5 out of 5 average rating, 36 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.93 out of 5 average rating, 42 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 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!
Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.94 out of 5 average rating, 35 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars2 weeks 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!
Superhost
A shaded stone terrace is surrounded by lush greenery, featuring a rustic wooden table with a variety of fresh dishes, fruits, and bottles. Two large trees provide ample shade, while two lounge chairs are positioned nearby, offering a serene outdoor dining or relaxation spot.
Home in Paciano
4.79 out of 5 average rating, 168 reviews

Traditional stone house in Umbria.

TimRating, 5 stars2 weeks ago
It's idyllic. A short drive or walk from Paciano and you get to this peaceful spot that looks over the olive grove. It's a fantastic spot to unwind and relax. The terrace is a beautiful shaded spot to while away the hours. We would highly recommend to anybody looking for the ideal spot to switch off and hear nothing but birds, bullfrogs and the occasional donkey bray. The home itself is well appointed, perfect for a couple or those with one child. There is plenty of space and the flat contains everything you need. We loved it. A perfect week.
Top guest favorite
A private swimming pool is surrounded by a stone patio, featuring several lounge chairs arranged for sunbathing. Lush greenery and olive trees provide a natural backdrop, while the distant view showcases parts of the historic borgo. A shaded area is available for relaxation.
Home in Montebenichi
5 out of 5 average rating, 59 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

SusanRating, 5 stars3 weeks ago
Our stay in Montebenichi was almost indescribable. Having been to Tuscany before, this time was pure magic. The flat is within the compound of a 12th century fortress village that is mostly inhabited by residents. Tommaso had stocked the kitchen with plenty of coffee, milk, water, juices, snacks and his grandmother's amazing Limoncello! The pool area has the most incredible view with an outdoor kitchen where Tommaso arranged for us to have a traditional Tuscan cooking class. He also made reservations for us at the village Michelin-rated restaurant that is just steps from the flat. One of our favorite things was hearing the wolves of Tuscany howl in the distance - no need to be afraid - it was pure magic. We saw very few tourists which made the experience even better. Moreover, Tommaso was THE BEST HOST we have ever had while staying at an Airbnb. His dedication to ensuring the perfect stay for us was truly a standout. We can not say enough good things about our stay!
Top guest favorite
The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.
Home in Tavarnelle Val di Pesa
4.96 out of 5 average rating, 296 reviews

Casa Al Poggio & Chianti view

KathyRating, 5 stars2 weeks ago
Hands down our favorite part of our two weeks in Italy! Casa Al Poggio was our Tuscan home away from home. We went and did all the things… Florence, Cinque Terre, San Gimignano, Montepulciano, etc. But coming “home” to this place was the best. So peaceful and picturesque looking across the valley at the Badia Di Passignano. We cooked many meals in the well stocked kitchen and my husband loved the rustic BBQ. Fresh herbs in the garden and the smell of jasmine blooming on the patio. Book yourself extra time here…you won’t want to leave! Emanuele & Tamara are the kindest people. Take them up on all of their restaurant recommendations. Everyone one was a hit! We can’t wait to go back.
Top guest favorite
A scenic view of rolling green hills stretches across the horizon, dotted with trees and farmland. A patio umbrella and lounge chairs are positioned outside, inviting relaxation. The sky is partly cloudy, with soft sunlight illuminating the landscape.
Home in San Giovanni d'Asso
5 out of 5 average rating, 62 reviews

Country chic house in a village,private pool,wiFi

PennyRating, 5 stars1 month ago
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!
Top guest favorite
A welcoming dining area features a wooden table set with plates and glassware, accompanied by fresh fruit. A bouquet of flowers sits on an adjoining console, while a television displays scenic imagery against a warm, yellow wall illuminated by wall-mounted lighting.
Home in Pienza
5 out of 5 average rating, 54 reviews

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

AaronRating, 5 stars4 days ago
One of the nicest places I’ve stayed. Like a luxury well decorated boutique hotel. But in Tuscany! We were 3 couples, each had their own room and bathroom.

Private house rentals

Top guest favorite
A cozy dining area is seen through open double doors, revealing a view of the green garden outside. Wooden chairs surround a table, while a rustic cabinet adds to the charm of the space. Natural light enhances the warm ambience.
Home in Castiglione d'Orcia
4.96 out of 5 average rating, 94 reviews

Da nonna Ornella - nest in Val d'Orcia

준우Rating, 5 stars5 days ago
Apart from the fact that communication was a little disappointing (this can also be communicated through a translator), it was really the best accommodation. I want to give a perfect score to everything from the location to the host. Our honeymoon was perfect because of the fantastic scenery and the warm and considerate kind diva. It's too far, but if I get the chance, I definitely want to come back. We pay respect, gratitude, and tribute to Diva for giving us the best experience. You are the best, Diva!
Top guest favorite
Rustic wooden windows are open, framing a scenic view of rolling hills, cypress trees, and distant buildings. Natural light pours into the room, highlighting the stone sill and surrounding walls.
Home in Monticchiello
5 out of 5 average rating, 41 reviews

Lovely home to dream

CadeRating, 5 stars1 week ago
This place is definitely a piece of Tuscany Italy. it will always hold a special place in my wife's and my heart with how beautiful and amazing the house was and the town it is located in. it seemed very well located, close to hot springs, multiple other cities, beautiful country side with horse back riding, world class winery's, ect. She is a great host and I would highly recommend this Airbnb to anybody looking for a one of a kind experience in Italy.
Guest favorite
A charming stone building features a textured exterior with a set of wooden shutters. A sturdy iron railing leads up to the entrance, with steps framed by potted plants. The clear blue sky and surrounding greenery enhance the inviting appearance of the home.
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 favorite
The image displays a panoramic view of Montepulciano, showcasing an array of rustic buildings with terracotta roofs. The landscape features rolling hills in the background, and a green garden is visible in the foreground, enhancing the historic charm of the area.
Home in Montepulciano
4.95 out of 5 average rating, 21 reviews

Hortus Conclusus House

MichelleRating, 5 stars1 week ago
Apartment was centrally located in the town. Very walkable to shops and restaurants. Beautiful sunrises through bedroom window. Very responsive hosts, especially with getting to the apartment from the train station (no Uber or taxi services when we arrived, so my advice is to get off at the previous stop if coming from Florence or make advance taxi arrangements). The hosts were very helpful and called their go-to cab driver. Beautiful with town and can’t wait to return!
Top guest favorite
An exclusive terrace features two cushioned chairs facing a small table, set with two glasses and a plate of snacks. The view spans rolling countryside and distant hills, with soft twilight colors enhancing the serene atmosphere of the outdoor space.
Home in Montalcino
4.94 out of 5 average rating, 33 reviews

Domus Antiqua

KellyRating, 5 stars2 months ago
We loved staying in this beautiful home in Montalcino. It was even more beautiful and unique than the pictures! My family of five loved staying here- lots of space for everyone and it was fun to be right in the 500 year old town. We especially love having coffee and wine on the balcony.
Superhost
A warm living area features arched windows allowing natural light to fill the space. A wooden coffee table is positioned in the center, surrounded by a comfortable sofa and a rattan chair. Shelving units display decorative items and a small plant sits atop the table.
Home in Lucignano
4.83 out of 5 average rating, 41 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.
Superhost
An outdoor terrace features a small table and two chairs, surrounded by lush greenery and a stone wall. The view overlooks rolling hills, allowing a glimpse of the landscape beyond. The apartment entrance showcases rustic wooden doors, enhancing the historical charm of the setting.
Home in Montepulciano
4.86 out of 5 average rating, 50 reviews

the birds view

AntonRating, 5 stars2 weeks ago
The apartment was in a great location. Sunsets have been etched in the retina forever :) What a great view! Easy walking distance to all restaurants and other attractions in Montepulciano.
Guest favorite
An open living space showcases a blend of modern design and rustic charm, featuring a comfortable sofa with bright cushions. A wall-mounted television is positioned below minimalist cabinetry, while a dining area with wooden accents is visible in the background.
Home in Montepulciano
4.95 out of 5 average rating, 62 reviews

La finestra - Montepulciano's historic center

MarkRating, 5 stars5 days ago
Paola’s place is very quiet and comfortable with spectacular views. Her apartment is a short walk to the center of town and the public parking area. Paola ’s communication was very good, from providing videos to show where to park, restaurant recommendations (and help with reservations) and regularly checking in on us. Highly recommended!

Destinations to explore

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