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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 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.
Guest favorite
A serene outdoor space features a turquoise pool surrounded by well-maintained grass and trees. Comfortable sun loungers are placed beside the pool, and a gazebo with seating provides shade. Lush greenery and decorative planters enhance the garden's aesthetic.
Home in Florence
5 out of 5 average rating, 9 reviews

La Limonaia della Torretta

OksanaRating, 5 stars1 week 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 favorite
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 favorite
Home in San Lorenzo
5 out of 5 average rating, 22 reviews

Casa dei Vasi

MaxRating, 5 stars2 days ago
What a beautiful place. So tranquil. Despite other guests being in the other houses dotted around the same garden we never bumped in to them - it felt private and intimate. The garden is so beautiful, well looked after with good views down the valley. The house is cool and quiet, felt rustic and authentic but not dated or dusty, it managed to strike that balance really well. Lorenzo was super helpful and responsive, always quick to let us know about the place and had loads to recommend in the area. And Alba, the matriarch of this oasis, was just the sweetest and warmest person ever. So friendly and welcoming. She gave us both a big hug when we got there and I only wish I spoke some Italian to be able to thank her for everything. She brought us loads of delicious baked goods and just seemed so happy to have us there. Overall a really wonderful and memorable trip. The only regret is not booking one week later! The day we left the pool opened for the summer. We'll just have to come back!
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.
Superhost
A serene outdoor space is featured, with a shared swimming pool surrounded by lush greenery and neatly trimmed hedges. Several sun loungers are positioned nearby under shaded umbrellas. The scenic landscape includes rolling hills and scattered trees, contributing to the tranquil environment.
Home in Casanova
4.89 out of 5 average rating, 37 reviews

Casa Liliana

LaurienRating, 5 stars1 week 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 favorite
A private pool is situated within a spacious, well-kept lawn, surrounded by tall trees and lush greenery. Lounging chairs are placed beside the pool, providing a comfortable spot for relaxation. Clear blue skies create a serene atmosphere, enhancing the tranquil outdoor setting.
Home in Cortona
4.93 out of 5 average rating, 27 reviews

Beautifully restored villa with private pool

MartinRating, 5 stars4 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
A private swimming pool is framed by landscaped greenery, with steps leading into the clear water. The expansive water surface reflects the distant view of Lake Trasimeno and the surrounding landscape under a partly cloudy sky.
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
A private swimming pool is surrounded by lounge chairs and umbrellas, inviting relaxation. A hammock offers a serene spot to unwind. Lush greenery frames the pool area, and the apartment structure is visible in the background, blending with the natural landscape.
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
A two-level swimming pool is set amidst landscaped greenery, featuring a shallow area leading to deeper sections. Loungers are arranged in a sunbathing area surrounded by olive trees, while a rustic building is visible in the background, providing a scenic backdrop.
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
An aerial view highlights a spacious homestead surrounded by lush green fields and well-maintained gardens. The landscape features a combination of agricultural land and residential areas, with a road creating a natural separation between them. Trees provide a soft border to the property.
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.
Guest favorite
A serene outdoor pool with a stone border is surrounded by lush greenery, offering a peaceful view of the rolling hills in the distance. The bright blue water contrasts beautifully with the natural elements, providing a refreshing spot for relaxation.
Condo in Uzzano
4.81 out of 5 average rating, 21 reviews

Tuscan country apartment in a lovely olive grove

VeraRating, 5 stars8 months ago
Die Unterkunft ist wirklich ein Traum! Wir hatten eine schöne, erholsame Zeit bei Deborah. Der Pool und die Lage ist toll und Deborah gibt super Empfehlungen, ist total warmherzig und man fühlt sich wie zuhause. Und hat es so gut gefallen, dass wir nochmal wiederkommen möchten!
Superhost
A shared swimming pool is set within a serene garden, surrounded by olive trees. Comfortable lounge chairs are arranged around the pool, complemented by a neat patio area. The clear water reflects the sunlight, enhancing the inviting atmosphere of the outdoor space.
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 favorite
A spacious swimming pool is surrounded by manicured grass and framed by tall trees. Sun loungers are arranged on one side, and umbrellas provide shade, creating a relaxing outdoor space. A clear blue sky with scattered clouds adds to the serene atmosphere.
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.
Superhost
The swimming pool, surrounded by greenery, reflects the soft clouds above in its tranquil water. Two wooden lounge chairs sit on the grass near the pool, inviting relaxation in a serene setting amidst olive trees.
Condo in Fiesole
4.88 out of 5 average rating, 183 reviews

Poggiolieto Studio - on hills 10' from city center

美穂Rating, 5 stars1 week ago
10代の子ども3名と、合計4人で4泊させてもらいました。到着からチェックアウトまで、Chiaraさんはとても丁寧で親切に対応してくれました。スーパーマーケットへの買い出しに車を出してくれたり、帰りのサンタマリアノベッラ駅までの送迎も快く引き受けてくれて、感謝しています。バス停までも徒歩15分なので、車がなくても過ごせました。調味料がたくさん揃えられていて、自家製の無農薬オリーブオイルを使うことができました。調理道具も揃っていたので、娘たちはパスタを作って庭でランチしていました。オリーブオイルはお土産に購入させてもらったので、旅が終わってからも楽しみです。部屋は決して広くはありませんが、4人で楽しく過ごすことができました。中心部の喧騒から離れた郊外の心地よい丘でフィレンツェ滞在を満喫したい方にオススメします。

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
An aerial view showcases the expansive grounds of Villa Pergo, surrounded by lush greenery and fields. The infinity pool is highlighted, surrounded by sunbeds and shaded by cypress and ancient trees. The countryside landscape stretches into the distance, enhancing the villa's serene setting.
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
A shared infinity pool is surrounded by tall cypress trees, providing a tranquil atmosphere. Comfortable lounge chairs set along the poolside invite relaxation under the shade of a large umbrella. The lush greenery and rustic building in the background complement the serene setting.
Farm stay in Arezzo
4.97 out of 5 average rating, 224 reviews

Esplora la natura al centro di Vigneti Chianti

CameronRating, 5 stars1 week 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
The villa is surrounded by lush greenery and tall trees, providing shade to a spacious outdoor seating area with a pergola. Steps lead up to the entrance, framed by well-manicured hedges, while a stone barbecue area is positioned nearby.
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 favorite
A sunlit infinity pool is surrounded by a stone terrace adorned with comfortable lounge chairs and umbrellas. The tranquil landscape of rolling hills and trees extends in the background, complementing the rustic charm of the stone cottage structure.
Home in Pescia
4.84 out of 5 average rating, 19 reviews

Aurora by Interhome

Dr. KristinaRating, 5 stars6 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!!
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
A spacious room features polished black and white marble flooring, with large arched windows allowing natural light to fill the space. A glass-top table is elegantly set with decorative glassware, while a cozy seating area with a light-colored couch complements the tranquil ambiance.
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 !!

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 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

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