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Vacation rentals with a pool in Asciano

Find and book unique homes with a pool on Airbnb

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Popular amenities for Asciano rentals with a pool

House rentals with a pool

Guest favorite
Home in Arezzo
4.9 out of 5 average rating, 167 reviews

Interno Italiano

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Guest favorite
Home in Asciano
4.94 out of 5 average rating, 36 reviews

Family Forest - Piscina nelle Crete Senesi

JánRating, 5 stars1 week ago
Apartmán nás skutočne očaril, izby pekné, čisté s klimatizáciou, štýlové, v obývačke veľká Tv, kuchyňa so všetkým čo tu má byť. Samotný "rezort" bol na kopci s krásnymi výhľadmi, obrovská záhrada, bazén, všetko štýlové také Toskánske, okolie prenádherné, pohoda, kľud,pokoj, všetko čo tu potrebujete tak aj nájdete. Ako vravia Taliani, je to tu " Tutto bene"
Guest favorite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars3 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Guest favorite
Home in Certaldo
4.87 out of 5 average rating, 63 reviews

Paluffo Torre House

AzaleaRating, 5 stars2 months ago
Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.
Top guest favorite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
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!
Guest favorite
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Casa Vecchia

LucyRating, 5 stars2 weeks ago
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 :)
Superhost
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month ago
Valeria und Simone haben eine super schöne und saubere Wohnung! Wir haben uns von Anfang an sehr wohlgefühlt. Die Wohnung bietet einen super Ausgangspunkt für zahlreiche Wanderungen und Ausflüge. Während unseres Aufenthaltes haben wir immer gute Tipps und Ratschläge von den beiden bekommen. Unser Hund hat sich auch sehr wohlgefühlt und da das Grundstück komplett eingezäunt ist, konnte er sich frei bewegen. Wir würden jederzeit wiederkommen. Es war eine unglaublich schöne Zeit!
Guest favorite
Home in Rigomagno
4.96 out of 5 average rating, 101 reviews

House Rigomagno Siena

Marco JustusRating, 5 stars1 week ago
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.

Condo rentals with a pool

Guest favorite
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment

TomRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars1 month ago
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.
Superhost
Condo in Castelnuovo Berardenga
5 out of 5 average rating, 5 reviews

San Rocco - Bellavista - Castello di Bossi

GaiaRating, 5 stars10 months ago
La struttura è meravigliosa, immersa nel verde e con una piscina dalla vista incredibile. La camera era pulitissima e con tutti i comfort possibili. Abbiamo interagito molto con una gentilissima signora della reception, molto cordiale e disponibile. Il vino che abbiamo degustato inoltre era eccezionale , vale la pena soggiornarci anche solo per una notte! Estremamente raccomandato
Guest favorite
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 472 reviews

Casa Rebecca con piccola piscina privata

MonikaRating, 5 stars1 week ago
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.
Guest favorite
Condo in Rifredi
4.92 out of 5 average rating, 167 reviews

VILLA LE PERGOLE - Florence

JennaRating, 5 stars2 weeks ago
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.
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week ago
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!
Guest favorite
Condo in Sesto Fiorentino
4.95 out of 5 average rating, 100 reviews

Ginestra: Private Pool Overlooking Florence

LauraRating, 5 stars2 months ago
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.
Guest favorite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
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, ...)

Home rentals with a private pool

Guest favorite
Home in San Casciano In Val di Pesa
4.84 out of 5 average rating, 93 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

JanetRating, 5 stars2 months ago
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!
Guest favorite
Cottage in Barberino Tavarnelle
4.97 out of 5 average rating, 193 reviews

Stone House with Exclusive Pool Codilungo in Chianti

SarahRating, 5 stars2 weeks ago
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!
Top guest favorite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Esplora la natura al centro di Vigneti Chianti

BaileyRating, 5 stars2 weeks ago
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.
Guest favorite
Villa in San Miniato
4.85 out of 5 average rating, 41 reviews

Historic home with exclusive pool

AylaRating, 5 stars11 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 favorite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 47 reviews

Villa di charme sulle colline del Chianti

JessicaRating, 5 stars2 weeks ago
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.
Home in Panicale
4.91 out of 5 average rating, 22 reviews

Podere Molinaccio-Luxury Tuscan-style Eco Villa

KristinaRating, 5 stars5 days ago
Absolutely amazing stay at this villa. Pool was perfect, villa was stunning, AC was much appreciated in the 90 degree heat, and the host was one of the very best ever! She was as our personal concierge helping set up a private chef, olive oil and wine tasting, truffle hunting and more. We spent a week and could have stayed longer there is so much to explore in Umbria and Tuscany and we absolutely loved it!
Guest favorite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio nelle campagne toscane

LizRating, 5 stars9 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
4.94 out of 5 average rating, 97 reviews

Suite Casa Luigi con piscina esclusiva

DerekRating, 5 stars3 days ago
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 vacation rentals with a pool in Asciano

  • Total rentals

    510 properties

  • Nightly prices starting at

    G$10,455 GYD 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

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Asciano
  6. Rentals with pools