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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

LéaRating, 5 stars6 days ago
Nous avons adoré notre séjour chez Bernardino ! Le paysage est magnifique, l’endroit est très propre et la piscine est un vrai plus pour se détendre. Bernardino est un hôte attentionné, toujours à l’écoute et prêt à aider à tout moment. Merci pour cette belle expérience !
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

FrankRating, 5 stars6 days ago
Ein unvergesslicher Aufenthalt im Herzen der Toskana! Die Wohnung liegt traumhaft schön in der Natur – umgeben von sanften Hügeln, Weinbergen und unzähligen Olivenbäumen, die in der Sonne silbern schimmern und das Landschaftsbild einfach magisch machen. Die Aussicht ins Tal ist atemberaubend schön – man könnte stundenlang einfach nur dastehen und schauen. Der 28 Meter Pool? Besser geht es nicht – perfekt gelegen mit Panoramablick, absoluter Ruhe und einer Atmosphäre, die zur puren Entspannung einlädt. Was diesen Ort aber wirklich besonders macht, sind die Menschen: Jacopo, Sophia und ihre Kinder haben uns mit einer so herzlichen Offenheit empfangen, dass wir uns sofort wie bei guten Freunden gefühlt haben. Es ist einfach schön, solchen Menschen zu begegnen – authentisch, warm und voller Lebensfreude. Und dann war da noch Luba, die Schäferhündin – ein echtes Herz auf vier Pfoten! Sie hat uns jedes Mal mit solcher Freude empfangen, dass wir sie sofort ins Herz geschlossen haben.
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

SilvanRating, 5 stars4 days ago
Wir hatten eine wunderbare Woche in Lyndalls Haus in Lecchi in Chianti! Das Grundstück, das Haus und der Pool waren sogar größer und schöner als erwartet. Die Landschaft ist traumhaft – perfekt zum Entspannen. Die Küche war hervorragend ausgestattet, sodass wir fast jeden Tag gekocht haben. Auch die Restaurant-Empfehlung im Ort war ein Volltreffer. Wir haben uns rundum wohlgefühlt und würden jederzeit gerne wiederkommen. Vielen Dank, Lyndall!
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 und Simone haben eine super schöne und saubere Wohnung! Wir haben uns von Anfang an sehr wohlgefühlt. Die Wohnung bietet einen super Ausgangspunkt für zahlreiche Wanderungen und Ausflüge. Während unseres Aufenthaltes haben wir immer gute Tipps und Ratschläge von den beiden bekommen. Unser Hund hat sich auch sehr wohlgefühlt und da das Grundstück komplett eingezäunt ist, konnte er sich frei bewegen. Wir würden jederzeit wiederkommen. Es war eine unglaublich schöne Zeit!
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 stars5 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, 36 reviews

Family Forest - Piscina nelle Crete Senesi

JánRating, 5 stars1 week ago
Apartmán nás skutočne očaril, izby pekné, čisté s klimatizáciou, štýlové, v obývačke veľká Tv, kuchyňa so všetkým čo tu má byť. Samotný "rezort" bol na kopci s krásnymi výhľadmi, obrovská záhrada, bazén, všetko štýlové také Toskánske, okolie prenádherné, pohoda, kľud,pokoj, všetko čo tu potrebujete tak aj nájdete. Ako vravia Taliani, je to tu " Tutto bene"
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, 61 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

PiretRating, 5 stars4 days ago
We really enjoyed our stay at Tommaso's! The house is located in a lovely small village, very quiet and peaceful, surrounded by beautiful Tuscan nature. We even spotted a wild boar one early morning (so best to be cautious during early mornings and late nights). There’s a charming local restaurant just around the corner where we had a great dinner – Tommaso kindly helped us book a table for our first night, which was much appreciated. Nearest bigger shop is around 20-min drive. The house itself is spacious and well-equipped, we had everything we needed and more. Just a heads-up that the pool area is a short walk from the house (about 3 minutes), but so worth it. Communication with Tommaso was smooth and easy throughout. Thank you for a lovely 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 stars3 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, 55 reviews

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

AaronRating, 5 stars6 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 - nido in Val d’Orcia

준우Rating, 5 stars1 week ago
의사소통이 약간 아쉬운것 빼곤(이것도 번역기를 통해서 의사소통 가능)정말 최고의 숙소였습니다 위치부터 호스트까지 모두 만점을 드리고 싶어요 환상적인 풍경과 따뜻하고 배려심 넘치는 상냥한 디바가 있어서 우리의 허니문이 완벽했습니다 너무 멀지만 기회가 된다면 꼭 다시 오고 싶습니다 우리에게 최고의 경험을 선사해준 디바에게 존경과 감사와 경의를 표합니다 당신은 정말 최고에요, 디바!
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

Graziosa abitazione per sognare

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, 20 reviews

Noi 2 Vacanze in Fortino d'Amore

ShervinRating, 5 starstoday
We had a great stay at Antonio’s Place. Tbh. the pictures of the interior look better than in real life, but the balcony with the view and the location itself is simply one of a kind that you instantly forget everything else. If you want to experience the beauty of Tuscany, this is the right apartment.
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

EllaRating, 5 stars1 month ago
Wir hatten eine wirklich wunderbare Zeit in der Unterkunft! Sie ist genauso wie auf den Fotos: Sehr schön eingerichtet, ruhig und mit tollem Ausblick. Eines der schönsten Airbnbs, in denen wir bisher waren! Der Pool war leider geschlossen, dafür kann man aber in den umliegenden Seen schwimmen gehen. Wir waren nur zwei Nächte dort, wollen aber ganz sicher noch einmal wiederkommen und dann auch länger bleiben!
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 stars3 weeks ago
Asunto oli mahtavalla paikalla. Auringonlaskut on porautuneet ikuisiksi ajoiksi verkkokalvolle :) Upea näkymä! Helppo kävellä kaikkiin Montepulcianon ravintoloihin ja muihin kohteisiin.
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 - centro storico Montepulciano

MarkRating, 5 stars1 week 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