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Vacation rentals with a pool in San Gimignano

Find and book unique homes with a pool on Airbnb

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Popular amenities for San Gimignano rentals with a pool

House rentals with a pool

Guest favorite
Home in Florence
5 out of 5 average rating, 5 reviews

New Florence "Afrodite" suite with pool

DanielRating, 5 stars1 week ago
Wir waren im April drei Nächte in diesem Apartment und es entsprach genau den Bildern. Die Unterkunft ist großzügig, modern ausgestattet und das Bett sehr bequem. Besonders positiv: Die gute Anbindung mit dem Bus ins Stadtzentrum sowie die kostenlosen Parkplätze direkt an der Unterkunft. Ein kleiner Minuspunkt war die schwache Belüftung – trotz Klimaanlage war es recht feucht im Raum, sodass Kleidung morgens leicht klamm war. In der Dusche fehlten Ablagen für Duschgel und Handtuchhalter. Trotz dieser Kleinigkeiten war es ein sehr angenehmer Aufenthalt. Der Gastgeber war sehr freundlich und hat schnell reagiert. Wir würden definitiv wiederkommen und können die Unterkunft empfehlen.
Superhost
Home in Montopoli
4.93 out of 5 average rating, 42 reviews

Villa Due Pini Marti con piscina privata

UlrikaRating, 5 stars7 months ago
Mycket trevlig vecka i det mysiga huset och den fina omgivningen. Perfekt ställe att umgås med vuxna barn med respektive. Tillsammans göra utflykter och laga mat i det hemtrevliga köket och ha poolhäng. Fin vecka för oss som gillar Italien.
Guest favorite
Home in Florence
5 out of 5 average rating, 9 reviews

La Limonaia della Torretta

OksanaRating, 5 stars1 week ago
I had the most amazing experience staying at this beautiful villa in Florence. The location was perfect—peaceful, private, and surrounded by stunning views that took my breath away, especially from the parking area. The villa itself was incredibly cozy and charming—so well maintained and full of character. Honestly, I didn’t want to leave. I’d live there if I could! The pool was a dream—relaxing, and the perfect spot to unwind with the Tuscan countryside all around you. Our host, Leonardo, was absolutely fantastic—so friendly, welcoming, and helpful throughout our stay. You can tell he really cares about making guests feel at home. This place was everything I hoped for and more. I would 100% come back again. Highly recommend!
Top guest favorite
Home in Pistoia
5 out of 5 average rating, 8 reviews

Cottage di Campagna con Piscina “Il Melograno”

FedericaRating, 5 stars8 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 favorite
Home in Fornaci di Barga
4.87 out of 5 average rating, 75 reviews

Nature and relax with swimming pool

GiuliaRating, 5 stars5 days ago
Siamo stati solo 3 giorni e purtroppo abbiamo incontrato cattivo tempo, ma questo non ci ha impedito di sfruttare l'immenso giardino che con due bambini piccoli è stata la salvezza🙂 La casa offre molti spazi (eravamo due famiglie) lasciando modo di avere la giusta tranquillità e privacy all'occorrenza. Alessandro è stato molto disponibile e gentile e la sua mamma, che abbiamo conosciuto prima di andarcene, è una signora molto simpatica e affabile.
Guest favorite
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", casa con piscina ai piedi di Cortona

AlessandroRating, 5 stars4 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.
Superhost
Home in Casanova
4.89 out of 5 average rating, 37 reviews

Casa Liliana

LaurienRating, 5 stars1 week ago
We really loved our stay, the beautiful surroundings and the place was even better than the pictures. Alfredo was very responsive and friendly. Would really recommend if you’d like a peaceful stay with close proximity to local Tuscan villages to explore.
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 stars16 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 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.
Superhost
Condo in Rosignano Solvay-Castiglioncello
4.74 out of 5 average rating, 23 reviews

100mt from the sea - apt w/pool, wifi & tv

MarkusRating, 5 stars8 months ago
Wir haben uns hier zu viert sehr wohl gefühlt. Das Appartement war sauber und Fabio war stets erreichbar, wenn wir eine Frage hatten. Die Anlage inklusive Pool war sehr schön und die Nähe zu Meer, Restaurants und Einkaufsmöglichkeiten perfekt, um voll und ganz entspannen zu können. Wir können diese Unterkunft uneingeschränkt weiterempfehlen!
Top guest favorite
Condo in Bibbiena, AR
5 out of 5 average rating, 16 reviews

ideale per due + loggiato, piscina nella fattoria

ChloéRating, 5 stars9 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 favorite
Condo in Uzzano
4.81 out of 5 average rating, 21 reviews

Tuscan country apartment in a lovely olive grove

VeraRating, 5 stars8 months ago
Die Unterkunft ist wirklich ein Traum! Wir hatten eine schöne, erholsame Zeit bei Deborah. Der Pool und die Lage ist toll und Deborah gibt super Empfehlungen, ist total warmherzig und man fühlt sich wie zuhause. Und hat es so gut gefallen, dass wir nochmal wiederkommen möchten!
Superhost
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars20 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 favorite
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.
Superhost
Condo in Fiesole
4.88 out of 5 average rating, 183 reviews

Poggiolieto Studio - on hills 10' from city center

美穂Rating, 5 stars1 week ago
10代の子ども3名と、合計4人で4泊させてもらいました。到着からチェックアウトまで、Chiaraさんはとても丁寧で親切に対応してくれました。スーパーマーケットへの買い出しに車を出してくれたり、帰りのサンタマリアノベッラ駅までの送迎も快く引き受けてくれて、感謝しています。バス停までも徒歩15分なので、車がなくても過ごせました。調味料がたくさん揃えられていて、自家製の無農薬オリーブオイルを使うことができました。調理道具も揃っていたので、娘たちはパスタを作って庭でランチしていました。オリーブオイルはお土産に購入させてもらったので、旅が終わってからも楽しみです。部屋は決して広くはありませんが、4人で楽しく過ごすことができました。中心部の喧騒から離れた郊外の心地よい丘でフィレンツェ滞在を満喫したい方にオススメします。

Home rentals with a private pool

Guest favorite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 188 reviews

Stone House with Exclusive Pool Codilungo in Chianti

ElizabethRating, 5 stars1 week ago
Incredible location and hosts! The house was immaculate and exactly as described. We really had the best time and made use of all of the recommended restaurants and towns to visit nearby. We had an incredible trip and could not be more thankful to such kind hosts that made sure we had everything we needed and more.
Top guest favorite
Farm stay in Arezzo
4.97 out of 5 average rating, 224 reviews

Esplora la natura al centro di Vigneti Chianti

CameronRating, 5 stars1 week ago
We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.
Top guest favorite
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!
Guest favorite
Home in Pescia
4.84 out of 5 average rating, 19 reviews

Aurora by Interhome

Dr. KristinaRating, 5 stars6 months ago
Ein Paradies! Schwierige Zufahrt, die belohnt wird. Eine traumhafte Villa mit spektakulären Blick auf die Hügel der Toskana. Toll restauriert mit modernen und klassischen Anteilen, dazu noch eine absolute Ruhe, rundherum wunderschöne Natur. Ein Highlight: Der großzügige Indoor-Jacuzzi, wir haben eine wunderbare Woche gehabt, danke!!
Top guest favorite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 42 reviews

Villa di charme sulle colline del Chianti

WilhelmRating, 5 stars6 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 favorite
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 favorite
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 92 reviews

Suite Casa Luigi con piscina esclusiva

DanielleRating, 5 stars7 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 !!
Guest favorite
Villa in Castiglione d'Orcia
4.95 out of 5 average rating, 95 reviews

Wp Relais Villa Vignalunga

Hila & DeanRating, 5 stars2 weeks ago
Had the most amazing time in this beautiful place! Stayed for 5 nights, two families with young children, and felt at home once we got there. We were amazed by the design and surroundings. Not enough words to describe!

Quick stats about vacation rentals with a pool in San Gimignano

  • Total rentals

    530 properties

  • Nightly prices starting at

    ﺩ.ﺇ37 before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    320 properties are a good fit for families

  • Pet-friendly rentals

    240 properties allow pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

Destinations to explore

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