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Vacation rentals with a pool in Gaiole in Chianti

Find and book unique homes with a pool on Airbnb

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Popular amenities for Gaiole in Chianti rentals with a pool

House rentals with a pool

Guest favourite
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 Florence
5 out of 5 average rating, 4 reviews

New Florence "Afrodite" suite with pool

SarahRating, 5 stars4 days ago
Simone was great during our stay. Super responsive and helpful. The space was beautiful and comfortable for 2 people. Also, central to bus stops that get you into the city within 10 or so minutes. Would definitely recommend!
Guest favourite
Home in Florence
5 out of 5 average rating, 8 reviews

La Limonaia della Torretta

PhilippeRating, 5 stars8 months ago
Perfect stay in Leonardo's beautiful house. I highly recommend it to all travelers in Florence. The house is beautiful and the garden and the pool are extraordinary. Leonardo is extremely attentive and very kind. To be recommended absolutely.
Top guest favourite
Home in Pistoia
5 out of 5 average rating, 8 reviews

Cottage di Campagna con Piscina “Il Melograno”

FedericaRating, 5 stars7 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
Guest favourite
Home in Monte San Savino
4.99 out of 5 average rating, 69 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Tsz Kwan CarrieRating, 5 stars6 months ago
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.
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 stars3 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 favourite
Home in Certaldo
4.92 out of 5 average rating, 49 reviews

Converted barn in Tuscan olive grove

LydiaRating, 5 stars7 months ago
This has been by far one of the most perfect holiday villas we’ve rented! Nestled in the most peaceful of locations, the villa was absolutely charming! Waking up to the sounds of birds chirping was a definite mood booster! We were relieved to see that there were herbs, oils and cooking condiments ready to use. The pool was a huge bonus and we used it most days. Seeing as we went in August, the outdoor temperature was very very hot, but luckily the house remained cool with its air con system. For anyone who wants to escape the hustle and bustle and doesn’t mind hillside driving, we highly recommend it! I would just mention that a few more hooks in the bedrooms to hang things on would be beneficial but didn’t impact our enjoyment whatsoever! Thank you to Charly for excellent check in and check out instructions. Big hugs from the UK!
Superhost
Home in Lucignano
4.91 out of 5 average rating, 22 reviews

Casale con piscina privata

CarmenRating, 5 stars19 months ago
Wir waren als Großfamilie, mit 7 Erwachsenen und einem 11 Monat alten Baby, da. Der Ort ist optimal für eine größere Gruppe, auch weil die Schlafzimmer teilweise räumlich etwas auseinander liegen und so Privatsphäre möglich ist. Das ehemalige Bauernhaus ist sehr schön restauriert und jedes Schlafzimmer hat sein eigenes Badezimmer. Auch an Fliegengitter an den Fenster wurde gedacht. Der Pool ist mit seiner Größe herausragend und wurde jeden Tag gereinigt. In dem traumhaft angelegten und sehr gepflegten Garten, mit seinen schönen Büschen und vielen Olivenbäumen, haben wir uns sehr wohlgefühlt. Von Rossella bekamen wir gute Tipps, sie war sehr freundlich und hat uns persönlich zu guten Einkaufs-Adressen begleitet. Wir haben uns sehr wohlgefühlt und kommen gerne wieder!

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 stars15 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 Sovicille
5 out of 5 average rating, 3 reviews

Appartamento 2 camere e 2 bagni, cucina, piscina

MilanRating, 5 stars92 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 favourite
Condo in Bibbiena, AR
5 out of 5 average rating, 16 reviews

ideale per due + loggiato, piscina nella fattoria

ChloéRating, 5 stars8 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 Volterra
4.95 out of 5 average rating, 21 reviews

Trilocale con 2 camere e giardino privato, piscina

AtefRating, 5 stars8 months ago
nous avons passé un agréable séjour et Sylvia à été parfaite. rien à dire. merci.
Superhost
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars19 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, 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.
Guest favourite
Condo in Montieri
5 out of 5 average rating, 25 reviews

PodereCupiano "Le Fornaci"

LindaRating, 5 stars6 months ago
Francesco a été très accueillant et en plus, le site est magnifique et très bien entretenu. La piscine avec la vue sur les montagnes est vraiment superbe ! Un bel endroit pour se détendre en toute tranquillité. La route pour s'y rendre est un peu longue et très tortueuse, mais c'est souvent le cas en Toscane...

Home rentals with a private pool

Guest favourite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 187 reviews

Stone House with Exclusive Pool Codilungo in Chianti

LeeRating, 5 stars5 months ago
The Stone House was gorgeous - beautifully and thoughtfully decorated, with amazing views. It was private yet easy to get to many amenities/tuscany towns/wineries nearby. Emanuela and Giovanni were very responsive to our questions and requests. We requested for help to buy a bouquet of flowers to surprise our friend for her birthday on the day we arrive - not only did they take the time to help us buy it, they refused to let us pay for it! it was too cold for us to use the pool but I can imagine how wonderful it would have been if we could have used it. all in all, it was a great place to enjoy a dreamy tuscan holiday.
Top guest favourite
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 favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 223 reviews

Esplora la natura al centro di Vigneti Chianti

FrancisRating, 5 stars5 months ago
L’appartement de Rita est très bien situé dans la campagne tranquille près de la ville d’Aruzzo. L’environnement est soigné et Rita nous fais sentir bien accueillis et bienvenue dans sa jolie famille avec son mari Aliguero et sa fille Sonaly. La petite grange que nous avons occupé est totalement rénovée au goût du jour et équipée avec des des appareils de qualité. Notre séjour était mémorable et nous recommandons cet endroit sans hésiter. Merci Rita pour cet accueil chaleureux.
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!
Top guest favourite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 41 reviews

Villa di charme sulle colline del Chianti

WilhelmRating, 5 stars5 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 favourite
Villa in Cortona
4.93 out of 5 average rating, 46 reviews

Agriturismo Henni panoramic pool sauna and jacuzzi

SamuelRating, 5 stars8 months ago
Me and my friends had an amazing week. Great house, pool and many other thinks. Can highly recommend to try the pizza-stone oven. Our highlight was the amazing view over the surrounding area.
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 stars6 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 Gaiole in Chianti

  • Total rentals

    10 properties

  • Nightly prices starting at

    $98 CAD before taxes and fees

  • Total number of reviews

    150 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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