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Holiday rentals with a pool in Casole d'Elsa

Find and book unique homes with a pool on Airbnb

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Popular amenities for Casole d'Elsa rentals with a pool

House rentals with a pool

Top guest favourite
Home in Barberino Tavarnelle
5 out of 5 average rating, 109 reviews

Infinity pool in Chianti

VeerleRating, 5 stars6 days ago
Dear Anna, nu we bijna terug een week in België zijn, dringt het nog meer tot ons door hoe prettig het verlof was in Toscane. Ik wil je hartelijk danken voor je goeie zorgen en betrokkenheid. We hebben zo genoten van je mooie huis -waar alles aanwezig was-, het mooie zwembad en de prachtige wijnhuizen en steden in de buurt. Ik wil je ook een dik compliment geven voor je prachtige planten op het hele domein. Het is niet simpel om die zo gezond te houden onder de Italiaanse zon. Kortom, ik zal je huis aan iedereen aanbevelen en wens je nog veel succes met de werken in het nieuwe, naburige huis. Veel groetjes aan je echtgenoot en zoon. Baci Veerle & co
Guest favourite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
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!
Guest favourite
Home in San Miniato
4.93 out of 5 average rating, 134 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars3 weeks ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
Superhost
Home in Figline Valdarno
4.96 out of 5 average rating, 108 reviews

The Owl: view, pool and garden

FrankRating, 5 stars6 days ago
Ein unvergesslicher Aufenthalt im Herzen der Toskana! Die Wohnung liegt traumhaft schön in der Natur – umgeben von sanften Hügeln, Weinbergen und unzähligen Olivenbäumen, die in der Sonne silbern schimmern und das Landschaftsbild einfach magisch machen. Die Aussicht ins Tal ist atemberaubend schön – man könnte stundenlang einfach nur dastehen und schauen. Der 28 Meter Pool? Besser geht es nicht – perfekt gelegen mit Panoramablick, absoluter Ruhe und einer Atmosphäre, die zur puren Entspannung einlädt. Was diesen Ort aber wirklich besonders macht, sind die Menschen: Jacopo, Sophia und ihre Kinder haben uns mit einer so herzlichen Offenheit empfangen, dass wir uns sofort wie bei guten Freunden gefühlt haben. Es ist einfach schön, solchen Menschen zu begegnen – authentisch, warm und voller Lebensfreude. Und dann war da noch Luba, die Schäferhündin – ein echtes Herz auf vier Pfoten! Sie hat uns jedes Mal mit solcher Freude empfangen, dass wir sie sofort ins Herz geschlossen haben.
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

SilvanRating, 5 stars4 days ago
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!
Top guest favourite
Home in Volterra
4.93 out of 5 average rating, 180 reviews

Podere Collina

DeanRating, 5 stars4 weeks ago
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!
Guest favourite
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.
Guest favourite
Home in Certaldo
4.91 out of 5 average rating, 130 reviews

Paluffo Stillo House

LeahRating, 5 stars3 weeks ago
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!!!

Apartment rentals with a pool

Guest favourite
Apartment 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 favourite
Apartment in Asciano
4.91 out of 5 average rating, 152 reviews

Appartamento Loggiato 3 in toscana vicino Siena

JanRating, 5 stars2 weeks ago
We hebben een onvergetelijke 14 dagen doorgebracht op deze droomplek. Het huis is prachtig gelegen op een heuvel met 360 graden kilometers ver schitterend uitzicht. Het is goed bereikbaar en centraal gelegen zodat vele bekende plekken in Toscane goed bereikbaar zijn. Het appartement heeft alles wat je nodig hebt om te koken, zelfs is er een Bialetti Moka koffiezetter aanwezig voor de liefhebber maar ook een gewoon koffiezetapparaat. De Coop supermarkt en bakker zijn binnen 15 minuten rijden te vinden. Anna, Francesca en hun team houden alles op en top schoon, ze zijn goed bereikbaar en spreken goed Engels. Ook hun moeder komt dagelijks langs om te controleren af alles in orde is. Bij het zwembad is het heerlijk vertoeven met een uitzicht waar je nooit genoeg van krijgt. Alles is uitstekend geregeld, iedereen heeft zijn eigen plekken buiten. Een top plek!
Guest favourite
Apartment 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.
Guest favourite
Apartment 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 favourite
Apartment 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
Apartment 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 favourite
Apartment 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.
Top guest favourite
Apartment in Castellina in Chianti
4.92 out of 5 average rating, 60 reviews

Apartment with terrace and stunning view

LeonRating, 5 stars2 weeks ago
Der Aufenthalt bei Raisa war unfassbar schön. Die Unterkunft und insbesondere die Aussicht ist noch viel schöner als auf den Bildern zu sehen. Raisa hat sich wahnsinnig viel Mühe gegeben uns alles zu angenehm wie möglich zu machen. Die Hunde (Saila und Yango) sind Mega knuffig, der Pool ist toll und das gesamte Anwesen echt malerisch. Mit dem Auto sind schöne Städtetrips etc. gut machbar und wir würden uns freuen irgendwann nochmal wieder zu kommen.

Home rentals with a private pool

Guest favourite
Home in San Casciano Val di Pesa
5 out of 5 average rating, 5 reviews

Sole by Interhome

MarkRating, 5 stars2 weeks ago
Incredible host. Incredible house. You feel like you are inside a postcard. The most beautiful views are all around you. We did not want to leave. Just breathtaking.
Guest favourite
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!
Superhost
Farm stay in Sovicille
5 out of 5 average rating, 7 reviews

Private Tuscan Villa, pool,Hot Tub, near Siena

CharleneRating, 5 stars13 months ago
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!
Top guest favourite
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.
Guest favourite
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 favourite
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.
Guest favourite
Home in Greve in Chianti
4.96 out of 5 average rating, 28 reviews

Casa 360 by Interhome

AnneRating, 5 stars1 month ago
I cannot say enough about how much we loved this place! The house is adorable, the views are spectacular and Borgo Savignola wine is outstanding! We were lucky enough to have Luzius prepare 2 dinners for us and they were both amazing. My family and I had a wonderful stay and truly hope to go back!
Guest favourite
Villa in Castiglione d'Orcia
4.95 out of 5 average rating, 102 reviews

Wp Relais Villa Vignalunga

MatthewRating, 5 stars1 week ago
Family of 5 here, 3 small kids. A wonderful stay! We toured surrounding villages in the morning and came back to the pool to beat the heat in the afternoon. The private cooking class with Valentina was the absolute highlight of the trip!

Quick stats about holiday rentals with a pool in Casole d'Elsa

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹5,160 before taxes and fees

  • Total number of reviews

    260 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Casole d'Elsa
  6. Rentals with pools