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Vacation rentals with a pool in Montalcino

Find and book unique homes with a pool on Airbnb

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Popular amenities for Montalcino rentals with a pool

House rentals with a pool

Top guest favorite
Home in Castiglion Fiorentino
5 out of 5 average rating, 36 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
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 Castellina in Chianti
4.98 out of 5 average rating, 111 reviews

StageROOM03 -Chianti Idillic Country living

DanielRating, 5 stars2 weeks ago
We loved the villa. It was private and had an incredible setting. Ivan was very responsive and incredibly helpful in suggesting restaurants and other activities. The only issue we had was finding the unit when we arrived. It was a little confusing at first to find our way to the villa.
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 Tavarnelle Val di Pesa
4.92 out of 5 average rating, 150 reviews

La Casa di Nada Home

ClaireRating, 5 stars1 week ago
We had the best week in Nada’s home with our friends who travelled from Australia. The villa was so cute and cosy and had everything you would need. Nada is a great host who was very responsive and extremely friendly, it was just a shame we didn’t get to meet her in person. The main highlight for us was when Viola (Nada’s daughter) came to the villa and did a cooking class with us. It was fantastic and one not to be missed! We made bruschetta, homemade pasta and sauce and a lemon tiramisu. We made pasta and bruschetta literally every night after as it was just so good. From the villa we travelled around in our hire cars and saw the delightful towns/villages such as San Giginano, Certaldo, Siena, Greve in Chianti, climbed up the hill to Montefioralle, Radda in Chianti, Volpaia and the local village of Barberino Val D’Elsa. I highly recommend you visit each as all close enough for a day out it combine a couple in a day. You will not be disappointed at Casa Di Nada. We loved it 😊
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 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 favorite
Condo in Monte San Savino
4.96 out of 5 average rating, 51 reviews

La Foresteria | Casa Granaio

RhiannonRating, 5 stars2 weeks ago
This place is even more beautiful than the photos show! We are travelling round Italy for our honeymoon and this has been our highlight. From the amazing grounds to the incredible food at the little restaurant it’s all been perfect. Thank you Marian for excellent communication and being so accommodating. What a fantastic place - Grazie!!
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.
Top guest favorite
Condo in Cinigiano
5 out of 5 average rating, 92 reviews

Appartamento Spinosa a Podere Capraia

FlorianRating, 5 stars2 weeks ago
We had a wonderful time at Alberto‘s and Laura‘s - it turned out that we didn’t do as many trips into the surroundings as planned because we just wanted to enjoy the beauty of the garden and the amazing views. It was the perfect ending of a fantastic vacation in Italy - I hope we will be back next year :) We received a fantastic welcome, home made bread, jam and pasta - and immediately felt like home. Grazie! One thing to mention is that the apartment is kind of thin-walled towards the second apartment - that didn’t bother us at all, but might be of interest for fellow travellers who are sensitive to noises. All in all, certainly one of the best accommodations we have stayed in!
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.
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!

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 Castiglione d'Orcia
4.67 out of 5 average rating, 30 reviews

Casa Frati by Interhome

JoJoRating, 5 stars2 weeks ago
Overall the location and charm of the property were stunning. Spacious bedrooms and living areas (beware uneven flooring, to be expected in an old farmhouse, my elderly father struggled). NOTE: we have not been asked for a cash deposit with Airbnb before and were surprised when a man came about 3 hours after we arrived to collect €400 cash. He spoke no English and used his phone to call someone who could speak to me. The host had not said he would be coming, or who he was. I contacted Airbnb support who said I could pay through the resolution centre. As others mentioned, there were no oil, salt, pepper etc, although a few dishwasher tablets. The jacuzzi and sauna work with tokens for €8 each. Didn’t use so not sure how long you get. BUT, this is a stunning property with unbeatable views in the heart of Tuscany, tucked away on a hillside down a gravel track. Would definitely book again. Pool is pristine, towels spotless, beds comfortable.
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!!

Quick stats about vacation rentals with a pool in Montalcino

  • Total rentals

    390 properties

  • Nightly prices starting at

    G$10,455 GYD before taxes and fees

  • Total number of reviews

    7K reviews

  • Family-friendly rentals

    270 properties are a good fit for families

  • Pet-friendly rentals

    250 properties allow pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

Destinations to explore

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