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Vacation rentals with a pool in Montalcino

Find and book unique homes with a pool on Airbnb

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Popular amenities for Montalcino rentals with a pool

House rentals with a pool

Guest favorite
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.
Superhost
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.
Superhost
Home in Città della Pieve
5 out of 5 average rating, 4 reviews

Casa Arcobaleno - Citta della Pieve

MarkRating, 5 stars8 months ago
Such a lovely villa. Beautifully arranged with perfect amount of space for our group of 8. The villa has everything you need. The pool was lovely and warm even without being heated. Margherita, the local host, was amazing - so helpful. Would definitely come back.
Top guest favorite
Home in San Lorenzo
5 out of 5 average rating, 21 reviews

Casa dei Vasi

ChristophRating, 5 stars2 weeks ago
Wir wurden super herzlich von Lorenzos Mama Alba begrüsst. Die Wohnung übertraf sogar noch deren Bilder. Wirklich sehr sehr schön und so gemütlich. Hat alles was es braucht. Herrliche Lage und sensationelle Atmosphäre. Die zahlreichen Tipps von Lorenzo waren alle Goldwert und wir haben jeden Tag aufs neue die Toskanische Küche geniessen können. Die kleine Stadt Anghiari ist traumhaft, ein wirklich schöner Ort mitten in der Toskana. Alles hat wunderbar geklappt, von der Kommunikation mit Lorenzo bis zur " täglichen Betreuung" durch Alba. Wir werden ihre liebevolle Art und Weise vermissen. Danke nochmals all die Leckerein. Dieser Ort und Unterkunft ist absolut empfehlenswert und immer eine Reise wert, auch für Familien (eher Kleinkinder). glg Fam.Fehrmann
Guest favorite
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
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.
Guest favorite
Home in Cortona
4.93 out of 5 average rating, 27 reviews

Beautifully restored villa with private pool

MartinRating, 5 stars3 days ago
We absolutely loved our two-week stay at Lucy and Tommy’s house. The house itself is beautiful, and the garden is truly a haven of peace - we spent so much time there, fully unwinding and recharging. From the moment we arrived, Lucy and Tommy were wonderful hosts, always available and incredibly helpful. They provided great local recommendations, and we were also lucky enough to try their delicious homemade olive oil. The house is located in an extremely peaceful area, surrounded by trees and nature, which made our stay even more relaxing. We can only highly recommend this accommodation and we truly hope to visit again in the future.
Top guest favorite
Home in San Feliciano
4.9 out of 5 average rating, 140 reviews

Casa dei 5 Sensi - Trasimeno view

MichelRating, 5 stars3 months ago
Maison très agréable à vivre, extrêmement calme, avec une vue superbe sur le lac Trasimène. Elle est située de manière excellente, puisque en 30 à 60 minutes de voiture on est aussi bien à Pérouse, Assise, Arezzo, Sienne et tant de belles autres villes. Et, pour qui préférera se promener à pied ou en vélo, le tour du lac fait presque 60 km ! Last but not least, Sergio est très sympathique, plein d'attentions mais tout à la fois très discret, et en homme de culture il vous donnera tous les renseignements que vous souhaiteriez. Pour une location au coeur de l'Ombrie et du sud toscan, ne cherchez pas ailleurs, c'est ici qu'il faut venir. Annette et Michel

Condo rentals with a pool

Superhost
Condo in Loro Ciuffenna
5 out of 5 average rating, 9 reviews

""Beautiful Villa with PRIVATE pool in Tuscany""

BahrinRating, 5 stars16 months ago
Nice scenary, quiet romantic Town, Nice small cafe beside the river. But what impress Me marco property I felt like Home right away. Secured electeric gate leaving Me no worries. Kids love it and kitchen are well equip!! Thanks marco for your beautiful place and hosting us!!! I recommend this place for quiet country side place.
Top guest favorite
Condo in Orvieto
4.97 out of 5 average rating, 38 reviews

Casa Eva, near Orvieto, amazing views + pool

JanaRating, 5 stars5 days ago
Cannot recommend this Airbnb more. So beautiful and the most amazing hosts. We felt at home and enjoyed every second of our stay. You truly feel like you are living in a dream. The pool was clean and the perfect way to enjoy the scenery.
Superhost
Condo in Sovicille
5 out of 5 average rating, 3 reviews

Appartamento 2 camere e 2 bagni, cucina, piscina

MilanRating, 5 stars93 months ago
We received very warm welcome and enjoyed very much Frederica's house, pool, pasta and last but not least Siena , San Galgano and San Gusmo' very much. The place is perfect and I don't remember other spaces from airbnb which can compete with this one. I hope we will be able to come again some time soon.
Superhost
Condo in Pergine Valdarno
4.67 out of 5 average rating, 6 reviews

Relax in farmhouse among the Chianti vineyards

MeganRating, 5 stars7 months ago
Tuscan retreat = THIS. Set in a lovely, quiet area with gorgeous views of the landscape. Easy to get to Arezzo and only 1 hour from Florence. So many amazing local restaurants and Vineyards. The property itself has a traditional vibe to it. The kitchen is not well equipped, so just bare that in mind! minimal pots, pans etc. But otherwise looks exactly like the photos.
Top guest favorite
Condo in Bibbiena, AR
5 out of 5 average rating, 16 reviews

ideale per due + loggiato, piscina nella fattoria

ChloéRating, 5 stars9 months ago
Nous avons passé un excellent séjour dans ce bel endroit. La ferme comporte plusieurs appartements avec chacun leur intimité. La piscine était très propre et chaude, il y avait de l’ombre à disposition et une douche et des toilettes juste à côté. L’appartement était comme sur les photos, il n’y avait pas de climatisation mais il faisait bien frais à l’intérieur la journée. Quelques jours avant notre arrivée, Isabella nous a envoyé toutes les informations nécessaires et c’est son frère Piero qui nous a très bien accueillis lors de notre arrivée. Le logement était très propre, la cuisine bien équipée et des linges de bain étaient fournis. Il y a beaucoup de choses à faire et à voir dans les alentours, nous avons même eu des recommandations à disposition. Dans l’ensemble nous sommes vraiment contents et nous recommandons vivement cet établissement!
Guest favorite
Condo in Volterra
4.95 out of 5 average rating, 21 reviews

Trilocale con 2 camere e giardino privato, piscina

AtefRating, 5 stars9 months ago
nous avons passé un agréable séjour et Sylvia à été parfaite. rien à dire. merci.
Superhost
Condo in Pian di Marte
4.67 out of 5 average rating, 6 reviews

Appartamento Nerone

GiuliaRating, 5 stars9 months ago
L'alloggio è un piccolo paradiso di tranquillità. zero inquinamento acustico. vista meravigliosa. ambiente curato e una bellissima piscina dove rilassarsi e rinfrescarsi. Antonella e la sua famiglia sono persone squisite, gentili e estremamente discrete. posizione strategica per visitare sia i villaggi del lago Trasimeno sia per visitare Perugia, Assisi e tanti altri posti. il borgo vicino è incantevole e si può fare la spesa di prodotti locali. per una spesa più complessa basta raggiungere il villaggio del lago (Passignano) e si trova coop e Conad. unico aspetto che va considerato è che l area è totalmente sprovvista di rete mobile. la casa è dotata di wifi però appena esci di casa anche solo per andare in piscina non hai modo di accedere alla rete. per chi come noi aveva voglia di staccare da tutto è stato un non problema. se invece avessi avuto bisogno di lavorare o essere reperibile va considerato. nel complesso per noi è stata una bellissima settimana di relax. vale la pena.
Guest favorite
Condo in San Casciano In Val di Pesa
4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

DavidRating, 5 stars6 months ago
My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.

Home rentals with a private pool

Guest favorite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 188 reviews

Stone House with Exclusive Pool Codilungo in Chianti

ElizabethRating, 5 stars1 week ago
Incredible location and hosts! The house was immaculate and exactly as described. We really had the best time and made use of all of the recommended restaurants and towns to visit nearby. We had an incredible trip and could not be more thankful to such kind hosts that made sure we had everything we needed and more.
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
Farm stay in Arezzo
4.97 out of 5 average rating, 224 reviews

Esplora la natura al centro di Vigneti Chianti

CameronRating, 5 stars6 days ago
We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.
Top guest favorite
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
Wir (7 Freundinnen) haben den Aufenthalt in der Villa sehr genossen! Das Haus, vor allem der Vorgarten und der Pool, sind wunderbar. Maria ist super! Sie hat uns sehr viele Tipps zur Umgebung zugesendet (auch die notwendigen Sachen, wie Einkaufsmöglichkeiten). Zudem wurden wir mit einem sehr feinen Kuchen überrascht und wenn man etwas brauchte, kam sehr schnell eine Antwort. Die Villa ist gut ausgestattet und die Umgebung wunderschön. Parkplätze hat es genügend. Einzig die Schlaglöcher und der Zugang zur Villa sind etwas herausfordernd - jedoch machbar!
Top guest favorite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 42 reviews

Villa di charme sulle colline del Chianti

WilhelmRating, 5 stars6 months ago
Wir haben ein paar schöne Herbsttage bei Francesca verbracht. Er ist viel schöner als auf den Fotos abgebildet. Das Haus ist traumhaft und ruhig auf einem Hügel gelegen. Die Ausstattung ist hochwertig und Francesca war stets kurzfristig zu erreichen. Wir würden auf jeden Fall wieder dort Urlaub machen.
Guest favorite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio nelle campagne toscane

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Guest favorite
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 92 reviews

Suite Casa Luigi con piscina esclusiva

DanielleRating, 5 stars7 months ago
Giovanna was such a wonderful host. It felt like a home away from home, with special touches added such as some food and wine in the apartment on arrival, and even a farewell drink before we left. The cottage is in breathtaking surroundings and in a perfect location to get around and explore different parts of Tuscany (with a car). I would highly recommend to anyone visiting the area ! We hope we can go back again one day!! Thank you Giovanna and Luigi !!
Guest favorite
Home in Castiglione del Lago
5 out of 5 average rating, 25 reviews

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

ChristopherRating, 5 stars6 months ago
We had a fantastic stay with a group of four adults and five kids. Accommodations were immaculate, private chefs were decadent and delicious, and fantastic wine. The grounds were just lovely as well and we enjoyed having a fire in the fire place every evening. That you for a lovely stay!

Quick stats about vacation rentals with a pool in Montalcino

  • Total rentals

    390 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    7K reviews

  • Family-friendly rentals

    270 properties are a good fit for families

  • Pet-friendly rentals

    250 properties allow pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montalcino
  6. Rentals with pools