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Vacation rentals with a pool in Castellina in Chianti

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Popular amenities for Castellina in Chianti rentals with a pool

House rentals with a pool

Guest favourite
Home in Florence
5 out of 5 average rating, 6 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.
Guest favourite
Home in Florence
5 out of 5 average rating, 10 reviews

La Limonaia della Torretta

OksanaRating, 5 stars2 weeks ago
I had the most amazing experience staying at this beautiful villa in Florence. The location was perfect—peaceful, private, and surrounded by stunning views that took my breath away, especially from the parking area. The villa itself was incredibly cozy and charming—so well maintained and full of character. Honestly, I didn’t want to leave. I’d live there if I could! The pool was a dream—relaxing, and the perfect spot to unwind with the Tuscan countryside all around you. Our host, Leonardo, was absolutely fantastic—so friendly, welcoming, and helpful throughout our stay. You can tell he really cares about making guests feel at home. This place was everything I hoped for and more. I would 100% come back again. Highly recommend!
Top guest favourite
Home in Pistoia
5 out of 5 average rating, 8 reviews

Cottage di Campagna con Piscina “Il Melograno”

FedericaRating, 5 stars8 months ago
Villetta incantevole nel relax totale. Tanto spazio verde e una bellissima piscina... tutto solo per noi. Giovanni è stato super accogliente e gentile. Un'esperienza da ripere, consigliatissimo! Un saluto da Fede e Kevin
Top guest favourite
Home in Piano di Coreglia
4.99 out of 5 average rating, 77 reviews

Casa del Sole

ChristianRating, 5 stars7 months ago
Nous avons passé un superbe séjour chez Carlo et Elena. Le jardin clôturé et la piscine étaient de vrais plus. Sans compter toutes les petites attentions que Carlo a pu avoir pour nous, et même un cadeau pour notre petit chiot. Le logement est paisible entouré de montagnes avec une belle vue. Nous recommandons cette maison et son hôte car tout était parfait!
Guest favourite
Home in Fornaci di Barga
4.87 out of 5 average rating, 75 reviews

Nature and relax with swimming pool

GiuliaRating, 5 stars1 week ago
Siamo stati solo 3 giorni e purtroppo abbiamo incontrato cattivo tempo, ma questo non ci ha impedito di sfruttare l'immenso giardino che con due bambini piccoli è stata la salvezza🙂 La casa offre molti spazi (eravamo due famiglie) lasciando modo di avere la giusta tranquillità e privacy all'occorrenza. Alessandro è stato molto disponibile e gentile e la sua mamma, che abbiamo conosciuto prima di andarcene, è una signora molto simpatica e affabile.
Guest favourite
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.
Superhost
Home in Casanova
4.89 out of 5 average rating, 37 reviews

Casa Liliana

LaurienRating, 5 stars2 weeks ago
We really loved our stay, the beautiful surroundings and the place was even better than the pictures. Alfredo was very responsive and friendly. Would really recommend if you’d like a peaceful stay with close proximity to local Tuscan villages to explore.
Guest favourite
Home in Cortona
4.93 out of 5 average rating, 27 reviews

Beautifully restored villa with private pool

MartinRating, 5 stars1 week 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.

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.
Superhost
Condo in Pergine Valdarno
4.67 out of 5 average rating, 6 reviews

Relax in farmhouse among the Chianti vineyards

MeganRating, 5 stars8 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.
Superhost
Condo in Rosignano Solvay-Castiglioncello
4.74 out of 5 average rating, 23 reviews

100mt from the sea - apt w/pool, wifi & tv

MarkusRating, 5 stars8 months ago
Wir haben uns hier zu viert sehr wohl gefühlt. Das Appartement war sauber und Fabio war stets erreichbar, wenn wir eine Frage hatten. Die Anlage inklusive Pool war sehr schön und die Nähe zu Meer, Restaurants und Einkaufsmöglichkeiten perfekt, um voll und ganz entspannen zu können. Wir können diese Unterkunft uneingeschränkt weiterempfehlen!
Top guest favourite
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 favourite
Condo in Uzzano
4.82 out of 5 average rating, 22 reviews

Tuscan country apartment in a lovely olive grove

LennartRating, 5 stars1 week ago
Deborah ist eine tolle Gastgeberin. Sie hat sich wunderbar um uns gekümmert. So eine tolle Gastgeberin hatten wir noch nie. Die Umgebung ist sehr schön für einen erholsamen Aufenthalt in der Toskana und ein guter Ausgangspunkt um die Gegend zu erkunden. Wir können Deborahs und Katias Ferienwohnung nur weiterempfehlen.
Superhost
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars20 months ago
We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!
Guest favourite
Condo in San Casciano In Val di Pesa
4.83 out of 5 average rating, 216 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.
Superhost
Condo in Rosignano Marittimo
4.86 out of 5 average rating, 7 reviews

Flat with private covered terrace,pool,very quiet

KitiRating, 5 stars9 months ago
Autentisk, roligt og ukompliceret. Skønt sted. Alt pænt og rent. Smukke og velholdte omgivelser. Poolområdet var en klasse for sig - så lækkert! Der er kun tre lejemål, hvilket gør det meget hyggeligt. Mr. Andrea sørgede for, at alt var ok og i orden - meget imødekommende, men med begrænsede engelsk kundskaber - det gik dog fint med Google translate og almindelig sund fornuft. Mulighed for skønne ture til nærområdet: Cecina er hyggelig og lidt “klassisk” turistby. Her var vi på det ugentlige marked samt spiste aftensmad på marina promenaden med den smukkeste solnedgang. Her er også fine strande. En bil er en nødvendighed. Mr. Andrea spurgte om alt ok. Jeg svarede, at det var perfekt. Han svarede, at ingenting er perfekt. Mit svar hertil var: jo, det her sted var!

Home rentals with a private pool

Guest favourite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 189 reviews

Stone House with Exclusive Pool Codilungo in Chianti

JacquelineRating, 5 stars2 days ago
Emanuela and Giovanni were wonderful hosts! The villa was beautiful. Everything was wonderful. We felt right at home. The scenery was incredible. The garden and pool were wonderful. They left us essentials to get us started like coffee, milk, bread and a bottle of wine. Kitchen had everything we needed. Located in the heart of Chianti. Overall, it was excellent. Highly recommend!
Top guest favourite
Home in Pergaccio
5 out of 5 average rating, 47 reviews

Villa Pergo is an ancient charming country villa

TerriRating, 5 stars7 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 favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 225 reviews

Esplora la natura al centro di Vigneti Chianti

MelissaRating, 5 stars1 week ago
Absolutely loved our family stay at Rita’s place. It was such a perfect spot - location was amazing! So clean! We can’t wait to be back xo
Top guest favourite
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!
Guest favourite
Home in Pescia
4.84 out of 5 average rating, 19 reviews

Aurora by Interhome

Dr. KristinaRating, 5 stars7 months ago
Ein Paradies! Schwierige Zufahrt, die belohnt wird. Eine traumhafte Villa mit spektakulären Blick auf die Hügel der Toskana. Toll restauriert mit modernen und klassischen Anteilen, dazu noch eine absolute Ruhe, rundherum wunderschöne Natur. Ein Highlight: Der großzügige Indoor-Jacuzzi, wir haben eine wunderbare Woche gehabt, danke!!
Guest favourite
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 favourite
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 favourite
Villa in Castiglione d'Orcia
4.95 out of 5 average rating, 95 reviews

Wp Relais Villa Vignalunga

Hila & DeanRating, 5 stars2 weeks ago
Had the most amazing time in this beautiful place! Stayed for 5 nights, two families with young children, and felt at home once we got there. We were amazed by the design and surroundings. Not enough words to describe!

Quick stats about vacation rentals with a pool in Castellina in Chianti

  • Total rentals

    30 properties

  • Nightly prices starting at

    $111 CAD before taxes and fees

  • Total number of reviews

    630 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Wifi availability

    30 properties include access to wifi

Destinations to explore