
Holiday rentals with a pool in Asciano
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Top-rated rentals with a pool in Asciano
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House rentals with a pool

Cercis - La Palmierina
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!

Casa di Lyndall - Entire house with exclusive pool
Wir hatten eine wunderbare Woche in Lyndalls Haus in Lecchi in Chianti! Das Grundstück, das Haus und der Pool waren sogar größer und schöner als erwartet. Die Landschaft ist traumhaft – perfekt zum Entspannen. Die Küche war hervorragend ausgestattet, sodass wir fast jeden Tag gekocht haben. Auch die Restaurant-Empfehlung im Ort war ein Volltreffer. Wir haben uns rundum wohlgefühlt und würden jederzeit gerne wiederkommen. Vielen Dank, Lyndall!

Antico Borgo Ripostena – n. 8 Casa Vecchia
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)

Country House in the Crete Senesi
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!

House Rigomagno Siena
Wir hatten eine wunderbare Zeit in diesem absolut niedlichen Haus, das inmitten atemberaubender Natur liegt. Die Ruhe ist einzigartig – man hört nur das Zwitschern der Vögel, und hin und wieder zeigen sich Rehe am Waldrand. Einfach magisch! Der Pool war top gepflegt und man hatte richtig Ruhe. Ein echtes Highlight war für uns die Küche: So liebevoll eingerichtet und außergewöhnlich gut ausgestattet – das haben wir so noch nie erlebt! Der Gasherd und der hochwertige Backofen haben das Kochen zu einem Vergnügen gemacht. Gastgeber Diego war unglaublich freundlich, aufmerksam und herzlich. Man fühlt sich bei ihm sofort willkommen und bestens umsorgt. Ein perfekter Rückzugsort für alle, die Natur, Ruhe und liebevolle Details zu schätzen wissen.

Paluffo Stillo House
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!

Infinity view
Wir haben eine Woche in diesem Haus verbracht und waren rundum zufrieden. Die Lage ist ruhig und idyllisch, mit einem weiten Blick über die toskanische Landschaft – besonders vom Infinity Pool aus ein echtes Highlight. Der Pool ist sehr gepflegt und bietet genug Platz zum Schwimmen und Entspannen. Das Haus ist sauber, gut ausgestattet und geschmackvoll eingerichtet – modern. Küche, Badezimmer und Schlafzimmer waren in einwandfreiem Zustand. Die Gastgeberin war sehr freundlich, gut erreichbar und hat bei Fragen schnell reagiert. Der Check-in verlief reibungslos, alle wichtigen Infos wurden vorab zur Verfügung gestellt. Gerne jederzeit wieder!

Casa Bada - Farmers House
We had a wonderful time staying here for five nights. The views are truly breathtaking. We also spent our first night taking part in a cooking class with our lovely hosts which was a true highlight of our trip. Enjoying the pool was an added bonus. You won't regret staying here!
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

L'Oliviera, 2 bedrooms stylish apartment
Die Wohnung ist sehr geschmackvoll und hochwertig, wie auf den Bildern eingerichtet. Sehr bequeme Betten! Auch die Außenanlagen entspricht der Beschreibung und ist im Sommer sicher ein schöner Ort zum Verweilen auch für einen längeren Aufenthalt. Wir hatten am Abend ein Problem. Francesco war schnell erreichbar und war am nächsten Morgen nach Absprache da und hat es toll gelöst! Vielen Dank dafür!! Wir empfehlen diese Wohnung gerne weiter und würden wieder buchen, wenn wir wieder in der Toskana sind. Wir hatten eine sehr schöne Zeit!

Adalberto Apartment inside the Manor of Fulignano
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

Casa Rebecca con piccola piscina privata
Das Ferienhaus und der Garten mit Pool ist wunderschön. Das Haus ist liebevoll im eingerichtet im Toskana Stil. Alles war sehr sauber und es hat an nichts gefehlt. Wir haben uns wie zu Hause gefühlt und haben in den Betten sehr gut geschlafen. Benedetta und ihr Vater sind sehr liebe und hilfsbereite Gastgeber, die uns jederzeit unsere Fragen beantwortet haben und sehr gute Empfehlungen für Besichtigungen und Restaurants gegeben haben. Als unser Auto repariert werden musste ist der Vater mit uns in die Werkstatt gefahren und war bei der Übersetzung behilflich. Danke nochmals für die selbstlose Hilfe. Wir werden diesen schönen Urlaub immer als das kleine Paradies in Erinnerung behalten, das von sehr lieben Menschen geführt wird. Wir können es nur empfehlen.

VILLA LE PERGOLE - Florence
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.

House between Firenze, Arezzo, chianti e Siena
Nous avons été de suite sous le charme de cette propriété. Tout ici compose l'image qu'on peut se faire de la belle campagne Toscane. Tout en haut de la colline surplombant la vallée, la vue y est splendide et romantique. La propriété a été renovée avec le confort d'aujourd'hui tout en conservant son âme d'autrefois. On s'y sent de suite bien, l'energie est bienfaisante, la nature, les animaux, tout est en harmonie! L'accueil, la cuisine d'Oscar, la superbe piscine, la terrasse ombragée, les petits-dejeuners copieux fait maison! C'est plus qu'un coup de coeur, cet endroit est une pépite! Nous reviendrons!

La Casetta
Können wir absolut empfehlen ! Ist alles so wie im Text beschrieben und auf den Foto´s zu sehen. Liegt ca 2 km außerhalb vom total schnuckeligen Örtchen Casole de Elsa. Von Andrea + Barbara gab´s alle nötigen Infos zur Anreise und viele tolle Tipps vor Ort, immer mit den dazugehörigen Links. Zum Beispiel verzögerte sich unsere Anreise verkehrsbedingt auf ca. 22:15 Uhr. War kein Problem, wir standen in Kontakt und als wir ankamen, hat uns Andrea persönlich in Empfang genommen. Und wenn wir während unseres Aufenthaltes eine Frage hatten, kam immer sehr zügig eine Antwort. (Wo man in Siena am Besten parken kann, wie gelangt man am Besten nach Florenz, ...)

Casa Luna-Splendida vista piscina e natura toscana
A little paradise in Tuscany with the most breathtaking view. We spend alot of the days at the house, swimming in the pool, cooking and generally feeling at home! They surprised us with fresh cherries 🍒 a few times and were happy to explain the beautiful routes you can walk around. We will def be back! ❤️
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Podere Vignali by Interhome
We had a wonderful stay! The house is perfect for larger groups or families – everyone having their own bathroom was a real plus. It was very clean and well maintained, and the pool area was lovely and well cared for. The kitchen is well equipped, and the property overall offers plenty of space to relax. The surroundings are beautiful and peaceful – we spotted fireflies at night, heard owls, and even saw a porcupine! A true nature experience. We received great tips from the host’s father. Carlo and Giovanna were always very kind and helpful. Communication with the host was smooth and friendly throughout. The house is a great base for exploring the area, though you do need a car to reach most shops – the little store in Pari is charming but quite small. The road to the house is a bit bumpy, but manageable. All in all, a great place to unwind and enjoy time with family and friends. Thank you for everything!

Esplora la natura al centro di Vigneti Chianti
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

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!

Private Tuscan Villa, pool,Hot Tub, near Siena
Fabio’s house was absolutely wonderful! Janine was super helpful, and the place was so clean and comfortable. It fit our 2 large families easily! Thank you for letting us stay and relax and take in the gorgeous countryside!

Villa di charme sulle colline del Chianti
We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.

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
I looked at dozens of other ABBs before choosing Giovanna's place and I know I made the best choice after staying. The setting is absolutely beautiful and peaceful. Lounging at the pool was so nice. We had the pool all to ourselves which is hard to find with other ABBs. The home is a nice large space and very clean. The views out the window are great. Giovanna was so nice and welcoming just a wonderful person. We enjoyed having a drink with her and Luigi. I highly recommend her place.
Quick stats about holiday rentals with a pool in Asciano
Total rentals
510 properties
Nightly prices starting at
₹4,300 before taxes and fees
Total number of reviews
6.3K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
240 properties allow pets
Rentals with dedicated workspaces
120 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Lake Bolsena
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Kite Beach Fiumara
- Marina di Grosseto beach
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Tenuta Le Velette