
Holiday rentals with a pool in Castellina in Chianti
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Top-rated rentals with a pool in Castellina in Chianti
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House rentals with a pool

New Florence "Afrodite" suite with pool
Wir hatten einen tollen Aufenthalt in Florenz, Simone war sehr nett und wir konntetn sogar früher einchecken das war seeehr nett und hat uns vieles erleichtert. Simone hat sich auch während dem Aufenthalt nach unserem Befinden erkundigt. Der Parkplatz befindet sich nocht auf dem Grundstück aber es gab viele Möglichkeiten in unmittelbarer Nähe zu parkieren.

Villa Due Pini Marti con piscina privata
Mycket trevlig vecka i det mysiga huset och den fina omgivningen. Perfekt ställe att umgås med vuxna barn med respektive. Tillsammans göra utflykter och laga mat i det hemtrevliga köket och ha poolhäng. Fin vecka för oss som gillar Italien.

La Limonaia della Torretta
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!

Cottage di Campagna con Piscina “Il Melograno”
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

Casa dei Vasi
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!

"Casa Elisa", casa con piscina ai piedi di Cortona
Het verblijf 'Casa Elisa' was beter dan we hadden verwacht. Het is een groot huis met zelfs een kelder met sauna. Het zwembad in de tuin (met buitendouche en toilet) en het huis zelf waren brandschoon. Er was geen stofje of spinnenweb te ontdekken (zelfs niet achter een kast die wij verschoven om bij een stopcontact te kunnen). Het uitzicht vanaf het balkon was adembenemend en de omgeving was fantastisch. Je bent zo in plaatsjes zoals Siena, Arezzo, Perugia en er is vlakbij ook een groot meer waar wij een dag een bootje hebben gehuurd (aanrader). Kortom, we kunnen het iedereen aanraden om bij Lorenzo te boeken. De communicatie met Lorenzo was ook uitstekend, goed te bereiken via app en spreekt goed Engels. Zijn vader komt elke dag even het zwembad checken en schoonmaken en zijn moederdag heel lief een heerlijke taart gebakken.

Casa Liliana
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.

Beautifully restored villa with private pool
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

""Beautiful Villa with PRIVATE pool in Tuscany""
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.

Relax in farmhouse among the Chianti vineyards
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.

ideale per due + loggiato, piscina nella fattoria
Super Unterkunft, noch schöner als auf den Bildern und mit sehr herzlichen und hilfsbereiten Gastgebern :) Das stattliche Anwesen ist wunderschön gelegen mit vielen Tieren und herrlichen Blick über die Ebene. Das ganze Casentino Valley ist gut mit dem Fahrrad, Bahn oder Auto zu erreichen. Besonders Freundlich war es für uns Unterstützung von den Gastgebern bei der An-und Abreise mit dem Zug zu erhalten und Fährräder für Unternehmumg vor Ort zur Verfügung gestellt zu bekommen. Leider war das Wetter Anfang Mai nicht so gut, aber sonst alles einfach wunderschön! Vielen Dank!

Trilocale con 2 camere e giardino privato, piscina
nous avons passé un agréable séjour et Sylvia à été parfaite. rien à dire. merci.

Tuscan country apartment in a lovely olive grove
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.

Luxury Views aircon Shared Pool parking cooking
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!

lovely farm- apartment (Fox)
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.

Poggiolieto Studio - on hills 10' from city center
Absolutely best place to stay near to Florence! We was tired of a car trip and decided to stay in Florence not in the city. And this apartment was best option! Super clean, easy to communicate and a lot of space on the territory of the house. Thanks Chiara and Giovanni!
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
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!

Villa Pergo is an ancient charming country villa
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

Esplora la natura al centro di Vigneti Chianti
Rita was an amazing host! She made everything easy. She is super warm and friendly. Genuinely kind. Her recommendations were spot on for the activities that we like. The apartment was adorable, and the grounds are beautiful. You can eat outside or swim. I hope we will be back. I highly recommend both Rita and her property.

Historic home with exclusive pool
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!

Aurora by Interhome
Wir hatten einen schönen Aufenthalt.

Villa di charme sulle colline del Chianti
Wir haben in im Haus von Francesca sehr wohl gefühlt, es ist eine Oase im Grünen mit einer herrlichen Aussicht auf Weinreben und Olivenbäumen. Das Haus ist es geschmacklos eingerichtet, die Kunst komplettiert das Ensemble. Der Pool und die Terrasse sind wunderschön für entspannte Urlaubstage. Einen Hinweis erlauben wir uns, es wäre schön, wenn bei der Objektbeschreibung klar gewesen wäre, das Francesca gleich im Nebenhaus wohnt.

Villa il Palagio nelle campagne toscane
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!!

Suite Casa Luigi con piscina esclusiva
Giovanna is a kind and welcoming host, and her place is gorgeous. We really enjoyed our time there, and would go back. The location is outside of town in Tuscany and it’s lovely and peaceful. The grounds are amazing. She’s truly a thoughtful host and this is a great place to stay.
Quick stats about holiday rentals with a pool in Castellina in Chianti
Total rentals
30 properties
Nightly prices starting at
$125 AUD 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
Wi-Fi availability
30 properties include access to Wi-Fi
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Parco delle Cascine
- Mercato Centrale
- Piazza della Repubblica
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- The Boboli Gardens
- Pinocchio Park
- Cavallino Matto
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Casa Barthel