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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 large terracotta vase is positioned beside a stone building, partially shaded by a lush tree. Surrounding greenery complements the natural setting, with a clear blue sky visible overhead, featuring a few scattered clouds.
Home in Civitella in Val di Chiana
4.93 out of 5 average rating, 45 reviews

Casa Fattore - Tuscan countryside house

LunaRating, 5 stars7 months ago
Il soggiorno alla tenuta di Capocontro è stato molto soddisfacente. L'intero borghetto antico è un gioiello incastonato nel verde, con vista spettacolare sui boschi della Val di Chiana. L'alloggio in ordine e pulito, pittoresco ed elegantemente retrò. Piero e Lella disponibilissimi nelle comunicazioni e nei suggerimenti di luoghi da visitare e in cui mangiare. Abbiamo amato la pace e il silenzio del luogo, nonchè la piscina con vista. Ci siamo fermati poco e il meteo è stato un po' capriccioso, altrimenti ci saremmo goduti di più gli esterni della fattoria. Unico piccolo neo: le stoviglie e il frigo non erano proprio immacolati, ma nulla che non si possa risolvere con un colpo di spugna. Super consigliato sia per un soggiorno breve che per uno lungo, così da godersi la quiete del luogo e visitare i dintorni.
Guest favorite
A private jacuzzi is featured in a cozy outdoor space, surrounded by wooden beams and landscaped greenery. Soft lighting enhances the serene atmosphere, inviting relaxation after a day of exploration. Steps lead up to the jacuzzi, providing easy access.
Home in Florence
5 out of 5 average rating, 5 reviews

New Florence "Afrodite" suite with pool

DanielRating, 5 stars1 week ago
Wir waren im April drei Nächte in diesem Apartment und es entsprach genau den Bildern. Die Unterkunft ist großzügig, modern ausgestattet und das Bett sehr bequem. Besonders positiv: Die gute Anbindung mit dem Bus ins Stadtzentrum sowie die kostenlosen Parkplätze direkt an der Unterkunft. Ein kleiner Minuspunkt war die schwache Belüftung – trotz Klimaanlage war es recht feucht im Raum, sodass Kleidung morgens leicht klamm war. In der Dusche fehlten Ablagen für Duschgel und Handtuchhalter. Trotz dieser Kleinigkeiten war es ein sehr angenehmer Aufenthalt. Der Gastgeber war sehr freundlich und hat schnell reagiert. Wir würden definitiv wiederkommen und können die Unterkunft empfehlen.
Superhost
An entrance features an arched doorway with exposed wooden beams above, leading into a courtyard. The terracotta tiles are complemented by potted plants, while a small seating area is visible in the background, creating a welcoming outdoor space.
Home in Montespertoli
4.83 out of 5 average rating, 70 reviews

Vacanza immersa nella campagna Toscana 'Canaiolo'

WernerRating, 5 stars7 months ago
We reached the destination and immediately felt like being at home. Such a nice country-house, quiet surroundings and a most gorgeous and large pool. Gary, who looks after everything, is one of the nicest hosts we have ever met: charming, helpful and making you feel very comfortable. A highly recommendable place to stay! Anne and Werner from Austria
Superhost
A spacious outdoor area features a large swimming pool surrounded by well-maintained grass. The pool area includes several white lounge chairs and is complemented by a nearby shaded seating space. Rustic stone buildings are visible in the background, amidst lush greenery.
Home in Todi
4.94 out of 5 average rating, 32 reviews

Villa in Umbria con piscina

MichaelRating, 5 stars8 months ago
Antonio ist ein sehr netter Gastgeber, der sich immer um das Haus und seine Gäste kümmert. Die 4 Wohnungen waren sehr gut und auch praktisch für unseren Gruppenurlaub. Parkplätze gibt es mehr als genug auf dem Grundstück, da Autos auch Pflicht sind um zum Haus zu gelangen. Des Weiteren ist der Pool sehr gut und auch sehr groß. Genug Platz um viel Spaß zu haben. Antonio kam mehrfach um den Pool auch zu reinigen, was sehr gut war. Gut wären noch weitere Schattenmöglichkeiten wie Schirme oder ein weiterer Pavilion da man die sonst vorher mitnehmen muss.
Guest favorite
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Top guest favorite
A red lounge chair is positioned on lush green grass, surrounded by tall cypress and olive trees. In the background, a rustic building is visible, partially covered by greenery, contributing to the serene outdoor environment.
Home in Campagnatico
5 out of 5 average rating, 7 reviews

Beautiful bright villa with view - Casa Luca

RafiRating, 5 stars1 month ago
We stayed at Mel's Casa Luca in March 2025 for over a week. Tucked away yet near medieval Campagnatico, it’s 5 minutes from the E78 to Grosseto/Siena, 15-20 minutes to Grosseto, and 30 minutes to the sea. Casa Luca, one of three stone farmhouses on what is essentially an olive farm, offers resort-like amenities which are shared with the guests of the other 2 houses: a trampoline, large pool, and ample walking space. Casa Luca is a single-storey house with two bedrooms with plenty of storage, comfy beds, an open-plan kitchen/dining/living area with Netflix, a big bathroom, and a well-equipped kitchen. Outside, there’s a private garden, terrace, BBQ. There is also a shared bakehouse with a pizza oven and huge dining table. We loved it and highly recommend it!
Guest favorite
The villa is set within a spacious green garden, surrounded by lush trees and rolling hills. Stone architecture is complemented by climbing plants, while terracotta roofs add warmth. The inviting outdoor space features well-maintained grass, creating a tranquil environment perfect for relaxation.
Home in Ficulle
4.96 out of 5 average rating, 23 reviews

Big Breathtaking PoolVilla bw Rm/Fl

PatrickRating, 5 stars8 months ago
Beautiful large house with great views and an amazing pool area. A little remote, at the end of a long and steep gravel road, but completely worthwhile. Great hosts, very attentive to their guests' every need.
Guest favorite
A private pool area is framed by lush greenery and blooming flowers. Two lounge chairs and a small table are arranged on a stone patio under a large umbrella. The bright yellow house is partially visible, showcasing an upper balcony.
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", casa con piscina ai piedi di Cortona

AlessandroRating, 5 stars4 months ago
Ho trascorso un soggiorno indimenticabile a Casa Elisa, situata ai piedi della splendida Cortona. L'atmosfera che si respira è magica: una fusione perfetta tra la tradizione toscana e il comfort moderno. Le camere sono eleganti e abbastanza spaziose, arredate con gusto e dotate di tutti i comfort necessari. Il giardino con piscina è un'oasi di tranquillità, ideale per rilassarsi con un buon libro o per godere di un aperitivo al tramonto. Ma è il calore e l'accoglienza della famiglia di Elisa a rendere il soggiorno davvero speciale. La loro disponibilità nel fornire informazioni sui luoghi da visitare e i ristoranti consigliati fa la differenza. Consiglio vivamente Casa Elisa a chiunque voglia scoprire la bellezza della Toscana, vivendo un'esperienza autentica e indimenticabile.

Weekly house rentals

Guest favorite
The living area features wooden beams across the ceiling and a cozy seating arrangement with a sofa and a bench. Large glass doors open to a garden, allowing natural light to fill the space. Decorative items are displayed on the shelves nearby.
Home in Figline e Incisa Valdarno
4.91 out of 5 average rating, 44 reviews

CAMPOPINETA MELOGRANO

SonjaRating, 5 stars7 months ago
CampoPineta ist ein guter Ort um sich zu erholen. Die Unterkunft hat alles was man braucht und ist sauber. Tolle Landschaft und gute Restaurants liegen in unmittelbarer Nähe. Wir hatten eine gute Zeit und Alessandra ist ein freundlicher Mensch.
Superhost
A spacious dining area is illuminated by natural light filtering through open doors. A large wooden table is surrounded by several chairs, and a matching sideboard displays glassware. Soft curtains frame the doorways, enhancing the charming countryside feel.
Home in Lucignano
4.78 out of 5 average rating, 9 reviews

Beautiful property between Siena and Arezzo

TimRating, 5 stars20 months ago
wir hatten einen sehr schönen Aufenthalt. Die gesamte Unterkunft war sehr sauber. Ich empfehle unbedingt etwas gegen die Stechmücken mitzunehmen. einziger Kritikpunkt waren die Stühle auf der Terrasse, da haben 2 stark gewackelt, es sollte hier Ersatz besorgt werden.
Superhost
Home in Umbertide
4.81 out of 5 average rating, 37 reviews

Private villa with pool and breathtaking views

SophieRating, 5 stars8 months ago
Anna’s house is stunning and tucked away in such a beautiful quiet location. The people who take care of the house were kind and our two year old loved him. Would highly recommend anyone who wants a quiet get away from the hustle and bustle of life to stay here.
Guest favorite
A wooden dining table is set with plates and glassware, complemented by a red table runner. A framed artwork hangs on the wall, and a rustic fireplace is visible, adding character to the cozy dining area. The adjacent kitchen is partially seen in the background.
Home in Greve in Chianti
4.88 out of 5 average rating, 115 reviews

La Meridiana a Montefioralle

TatyanaRating, 5 stars6 months ago
Eugenio was a great host. His place is super authentic, located in the most charming medieval village with spectacular views. Everything in the house was to our satisfaction. Eugenio was super responsive and helpful with accomodating some extra requests that we had. We were travelling for work, filming a wedding at nearby castel. Location was great for us. The public parking is only about 100 meters from the house. We were teally happy with everything. Thank you Eugenio. P.S. There is an amazing restaurant with spectacular views right in the village. They only do lunches. But wow, It was such a great find. Everyrhing in that restaurant was made from their own produce, wine from their vineyard in the valley, olive oil from their trees, all vegetables from their garden. Different set menue every day. Really recommend it. It was delicious.
Guest favorite
A spacious living room features a vaulted ceiling with terracotta tiles. Glass doors open to a scenic outdoor area, inviting natural light. Comfortable seating includes a light-colored sofa with decorative pillows and woven chairs, complemented by framed botanical art on the walls.
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

ClemensRating, 5 stars7 months ago
Wir hatten einen tollen Urlaub mit 9 Freunden. Das Haus liegt sehr ruhig und ist sehr hochwertig und liebevoll eingerichtet. Der Außenbereich war wunderschön und grün. Ein toller Pool und viel Platz ganz für sich alleine. Alles exakt wie beschrieben und auf den Bildern gezeigt. In der Nähe sind mit dem Auto viele schöne und günstige Restaurants erreichbar. Wir würden es auf jeden Fall weiterempfehlen und hatten eine schöne Zeit. Amanda war sehr freundlich und war immer schnell erreichbar bei Fragen.
Guest favorite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

Colombaio di Montebenichi

StephenRating, 5 stars1 week 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
Top guest favorite
The exterior of the two-story stone villa is framed by olive trees and garden flowers. Balconies with flower boxes adorn the upper level, while wooden shutters provide a rustic charm. Lush green space surrounds the property, enhancing its natural setting.
Home in Monte del Lago
4.97 out of 5 average rating, 30 reviews

Villa Profumo di Salvia. Fronte lago

AndrewRating, 5 stars6 months ago
We had a wonderful stay. Silvia was very responsive, and she even brought us pizza upon our late arrival! The grounds are gorgeous and the views were incredible. The villa itself was spacious, clean, and exactly as described in the listing. Highly recommended.
Superhost
A bright workspace is positioned in a cozy room featuring wooden beams. Multiple windows allow natural light to illuminate the wooden desk and chair. A lamp stands on the desk, while views of the surrounding landscape are framed by the windows.
Home in Impruneta
4.84 out of 5 average rating, 68 reviews

Independent house with private pool and garden

JulianeRating, 5 stars6 months ago
We had a wonderful time in Vittoria's house in this fantastic location. Although we had so many difficulties getting there and only arrived at night (flight delayed and highway closed), her husband greeted us very kindly and showed us around the house. Vittoria was always super quick to respond and always helped us (e.g. turned on the heating when it suddenly got cold). Highly recommended!

Private house rentals

Superhost
A spacious farmhouse exterior is surrounded by lush greenery, featuring a blend of trees and ornamental plants. The structure displays a large window and a covered area beside it, providing access to the outdoors in a tranquil setting.
Home in Castiglione della Pescaia
5 out of 5 average rating, 5 reviews

Family House Baldana

RobertaRating, 5 stars8 months ago
Era la nostra prima volta a Castiglione. Padrone di casa (mamma e figlia) gentilissime, accoglienti e disponibilissime. Posto meraviglioso, lontano dal caos cittadino ma a poca distanza dal mare, immersi nella natura e nella pace. Alloggio spazioso, dotato di tutto il necessario all'interno e all'esterno con sdraie, ombrellone e tavolo. Ci siamo sentiti come a casa. Grazie ancora di tutto. Torneremo sicuramente.
A rustic stone farmhouse is framed by a gravel courtyard, punctuated with potted plants and vibrant flowers. The structure features an arched entrance, wooden doors, and a tile roof. A shaded area is provided by nearby trees, enhancing the serene setting.
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!
The living and dining area is characterized by rustic wooden beams and terracotta flooring. A wooden dining table is set for meals, while a comfortable seating arrangement faces a fireplace. Natural light enters through a large arched window, complemented by a television in the corner.
Home in Castellina Chianti SI
5 out of 5 average rating, 4 reviews

Capanna di Sotto by Interhome

AndreasRating, 5 stars7 months ago
Sehr schöner und ruhig gelegener ehemaliger Bauernhof mit sehr netten und hilfreichen Gastgebern. Entspannung pur.
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, 32 reviews

Domus Antiqua

JonathanRating, 5 stars3 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
A charming pink house is surrounded by lush greenery and a gravel pathway. A fireplace can be seen on the exterior, and the windows provide natural light to the interior. The entrance features a decorative fence, enhancing the tranquil setting.
Home in Ampio
4.96 out of 5 average rating, 23 reviews

La casa di Anna

MarilenaRating, 5 stars7 months ago
Il mio compagno ed io abbiamo soggiornato per una settimana con il nostro cane di taglia media. Un soggiorno di relax, casa ampia e fornita e punto forte il giardino! Oltre a noi anche il nostro cane lo ha apprezzato tanto. Antonio e la moglie sono davvero gentili e disponibili, sempre pronti in caso di necessità Soggiorno bellissimo!
The exterior of the rustic stone house features a spacious terrace with tiled flooring and a wooden pergola. Lush greenery surrounds the area, and vibrant flowers add color to the landscape. The entrance is framed by opened double doors, inviting guests to explore.
Home in Cortona
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

J.Rating, 5 stars7 months ago
We hebben een goede tijd gehad bij Lucia. Stond altijd klaar. Ook de moeder van Lucia was erg vriendelijk. Huis was ondanks de 35 graden en geen airco toch koel genoeg met de ventilatoren. Vooral s’nachts. De horen waren top. Even zo het zwembad was geweldig. Uitval basis voor steden in Toscane was perfect.
Top guest favorite
A modern kitchen features a central island with an induction cooktop and seating for several guests. Gray cabinetry complements stainless steel appliances, including an oven and refrigerator. Natural light fills the space, highlighting the open-concept layout that connects to the living area.
Home in Castiglion Fiorentino
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars6 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.
Superhost
A spacious dining area is highlighted by a large wooden table surrounded by chairs. Exposed wooden beams and an arched window frame contribute to the rustic charm. A glass door allows natural light to illuminate the room, revealing a comfortable seating area in the background.
Home in Molino Vitelli
5 out of 5 average rating, 3 reviews

2 / 8px house on Tuscan Borders

ElizabethRating, 5 stars2 weeks ago
Andrea's place was perfect for our short two night stay in the Niccone Valley, or fav area in Umbria. We were there in cooler weather and the floor heating took a bit to come on but once it did we were comfortable. I think it would be a great place in the warmer weather as the pool looked wonderful. The Niccone Valley is somewhat remote but with the location of this property you had the best of both worlds quick access to Umbertide and yet embedded in the valley. Would love to return in the warmer weather. Thank you Andrea!

Destinations to explore

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