
House holiday rentals in Poggibonsi
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House rentals with a pool

Private villa/swimming pool in Tuscany
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!

Charming estate with views
Nous avons adoré notre séjour chez Bernardino ! Le paysage est magnifique, l’endroit est très propre et la piscine est un vrai plus pour se détendre. Bernardino est un hôte attentionné, toujours à l’écoute et prêt à aider à tout moment. Merci pour cette belle expérience !

Podere Tignano, 4-bedroom villa in the Chianti!
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Casetta Melograno - Cozy farmhouse in Chianti
I don’t have the words to describe how beautiful this apartment on the hillside is. The apartment itself is nice and cosy and spacious, and the kitchen contains a little bottle of olive oil produced from their own olives. But it is the location, the gardens and the little farm and the view across the valley which can take your breath away. Sonia is happy and welcoming and patient. She showed us around the wine and olive farm and was always approachable when we contacted her. There are two guest apartments side by side, but it is quite private nonetheless. Note that you can hear sounds from the other apartment quite easily. I cannot recommend this enough! Would love to come back.

The Owl: view, pool and garden
We stayed 5 amazing days at Il Gufo and loved every minute. Jacopo is an amazing host and went out of his way throughout to make our stay great. Even meeting us locally and showing us the way to the house. We highly recommend staying at The Owl. The location, high in a valley provides spectacular views and is perfect to relax and unwind. We do not know what was better. The location, accommodations or the fact that we met Jacopo and became immediate friends. That combination made for the greatest memories. Also Luba, their beautiful dog, immediately loved us and greeted us ever time we returned. A little secret, he is an amazing chef and if you get a chance to go to his restaurant do it. Also his dinner recommendations were great. We had dinner at Corte Dei Frati 2 times. Thank you Jacopo for making our 30th Anniversary trip so amazing. We feel privileged to have met you and we will return on our next trip to Italy. You are an amazing person and host. Love Steve & Vicki

Podere Collina
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!

Casa di Lyndall - Entire house with exclusive pool
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

Casa di campagna privata con giardino, Wifi e A/C
It gave us exactly what we needed, a private and calm place to relax with a beautiful view, lots of space by the pool, around the garden, and if we wanted to be on our own, in our separate space. The hosts were really friendly and had great suggestions for places to go and always were responsive in case we needed anything, but they also gave us the space we needed – just what we were looking for. Thank you for a great time in Tuscany!
Weekly house rentals

[Chianti]LOFT Garden free parking to San Gimignano
Giulia è stata molto disponibile per l'orario di checkin, già sul posto appena arrivati. Ci ha mostrato l'appartamento e dato alcuni consigli. È stata molto disponibile a cambiarci subito la coperta quando gli abbiamo comunicato che avevamo avuto caldo la notte. Appartamento come da foto. Lo consiglio come punto di appoggio; noi siamo labbiamo scelto per fare un operazione agli occhi alla clinica di Poggibonsi, a 5 minuti di macchina. Nei giorni successivi ci siamo spostati comodamente a San Giminiano, Certaldo, Siena, Monteriggioni e Firenze.

Villa Mocarello "IL CIPRESSO"
Abbiamo deciso d trascorrere il capodanno in questa località usandola come base per poterci spostare e scoprire le bellezze toscane. fin dal primo approccio, alla prenotazione, Fabio e Alessandra si sono dimostrati estremamente amichevoli e di supporto. tutte le indicazioni sono state precise,puntuali e dettagliate. l'accoglienza, da parte di Mamma Antonella è stata super calorosa e ci ha fatto sentire come se fossimo a casa. l'appartamento è estremamente curato, di ottimo gusto e pulitissimo. la cucina offre tutta la strumentazione necessaria e vi sono una serie di piccoli pensieri per gli ospiti molto apprezzati. Grazie davvero per questo splendido soggiorno,la vostra gentilezza e il calore con il quale ci avete accolto ha reso ancora più speciale questa esperienza

Tuscany .Countryhouse on the Florence's hills
We stayed at Flora House as a family trip with my parents and had a wonderful time. The house is beautiful, peaceful, and perfect for a relaxing vacation. The kitchen is very well equipped, and we really enjoyed cooking meals together with fresh ingredients from the host’s farm. It was a great place to unwind and spend quality time as a family. Highly recommended!

casa palme
Alessandra and her husband made us feel at home from the moment we walked into their home. It was absolutely beautiful! The boys loves playing hide and seek in all of there hidden compartments. I loved the view from their swing. Alessandra went above and beyond helping us with anything we needed. She even brought over a thermometer and medication when I told her I wasn’t feeling well. Her kindness and compassion meant so much to my family and I. I truly don’t have enough words to describe how grateful I am to have found this beautiful rental.

Agriturismo Podere San Martino (apartment for two)
Onwijs fijn appartement dat goed koel blijft tijdens warme dagen. Uitzicht vanaf het prive terras was adembenemend en het appartement was smetteloos schoon. Alles behalve een weegschaal om de koffer te wegen was aanwezig, echter die was binnen een half uur geleend van de ontzettend vriendelijke eigenaresse (die overigens olijfolie en honing van eigen kweek aanbiedt).

Casa Maurino
Such a wonderful gem of a place to stay. Views were top notch and all within walking to our favorite dinner restaurants and town center. Just an amazing experience and location. Rossana was a great host- very communicative. She decorated her place with really nice special touches. We will return!

THE BREATHE.Molino di Canonica. Original Apartment
Uns erwartete eine sehr schöne, spezielle Unterkunft, in der alles notwendige vorhanden war. Wir haben uns sehr wohl gefühlt. Bedingt durch die enge Straßenführung konnten wir leider mit den Fahrrädern nicht so oft fahren, mit dem Auto jedoch haben wir die Gegend ausführlich erkundet und die vielen wunderschönen Städte besichtigt.wir können die Unterkunft auf jeden Fall weiterempfehlen.

Montalcino Townhouse with Private Panoramic Garden & Spa
We loved staying in Montalcino at Lisa's place. Lisa was a fantastic host and responded quickly. She gave us her picks for restaurants, wine tastings, etc, which were excellent choices. The Airbnb was ideally situated right off the main square. It has a yard, which we enjoyed, and a very functional kitchen with everything we needed. The king-size bed was very comfortable and had high-quality linens. This is a hilltop city, so keep this in mind for anyone unable to walk up steeper inclines throughout the city. We enjoyed the exercise and the stunning views. We stayed for a week and I could have easily stayed longer as we got to know the restaurants, stores and the area. Montalcino is a charming place to spend your time. It was a good location from which to take day trips. There is so much to do in the general area. We highly recommend you stay here; it was the highlight of our trip, and we felt like we were in good hands. Thank you, Lisa!
Private house rentals

Family Forest - Piscina nelle Crete Senesi
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!

Apartment in ex-Torre in Ponzano Barberino V.E
Andrew e Albana si completano, ti fanno sentire subito il benvenuto e sanno metterti a tuo agio, persone con tanta esperienza di vita. Abbiamo apprezzato molto i biscotti, il caffè, il latte, tutto il necessario per fare un ottima colazione , compresa una bella bottiglia d'acqua che era fondamentale, sono quei piccoli gesti che fanno la differenza. Con Andrew potresti stare a parlare per ore senza mai stufarti, Albana invece ci ha dato delle belle dritte, specialmente sul parcheggio di villa Costanza, seguendo i suoi consigli abbiamo risparmiato tempo e fatica, il che non guasta mai. L' appartamento era pulitissimo, ben arredato e tranquillo. Grazie mille un abbraccio.

La casina ridente in Toscana con vista mozzafiato
Stella nos recebeu muito bem, foi simpática e prestativa. A casa estava muito limpa e organizada. O espaço e aconchegante. O lugar é extraordinário, muito bonito, com natureza exuberante e uma vista maravilhosa. Stella recomendou lugares para visitar e restaurantes da região que gostamos muito. Somente elogios, nenhuma reclamação.

Countryhometuscany - House with Garden -
We had a wonderful stay in this beautiful accommodation in Tuscany. The views are stunning, and the property includes a small, fenced garden, which was perfect for our dog. There's also a large pool available to all guests, which was a huge plus. Having a car is a must. The location is ideal for visiting local spots like Siena, San Gimignano, and Val d’Orcia. The host provides a fantastic guidebook with recommendations, and we were never disappointed by any of the places he suggested. The fully equipped kitchen made it easy to prepare meals, and we enjoyed relaxing dinners in the garden under the lights. Overall, it's a cozy and comfortable place, perfect for a Tuscan vacation

L'Uva Fragolina. House, Garden, Panoramic View
Ein Toskanischer Traum. An manchen Tagen musste ich mich kneifen um zu begreifen das ich nicht in einem Film bin. Meine Freundin und ich haben eine wunderbare Zeit in der Region und auch im Haus gehabt. Es war sauber und ordentlich. Die Küche war einzigartig und wir haben gerne auch draußen gegrillt. Wir haben es einfach genossen und uns wie zuhause gefühlt. Endlich mal Entspannung und Ruhe, die man nur noch selten erlebt. Vielen Dank für das Vertrauen über dieses wunderbare Stückchen Toskana. Für alle Ruhe suchenden oder Menschen die wirklich erleben wollen was Toskanischer Flair bedeutet ein Pflichtziel. Wir kommen gerne wieder!

Chianti House Stunning view 20 min. from Florence
What a place! An absolutely perfect little hideaway in an absolutely gorgeous location. This charming abode has exactly what you need to completely escape and soak in the stunning surroundings of the Tuscan landscape. Even though it rained quite a bit of our visit, sitting on the veranda overlooking the pool and rolling hills nice and dry under the tent was magical - the lush view could never get old! The stone space is as quiet and cozy as can be - comfortable bed and couch, very functional kitchen, nice bathroom. Pretty antiques make the space homey. My husband even jumped in the very cold pool in the rain and now we want to come back in the summer sun to enjoy it more. Tommaso was incredibly sweet and offered recommendations and walked us through the whole place upon check in - and he was kind and responsive the whole time. Really can’t recommend this experience enough!

La Cipressina Relax in Tuscany
Wir haben uns sehr wohlgefühlt. Sogar an unser Baby wurde gedacht und extra Utensilien bereitgestellt. Die E-Ladestation konnten wir nicht gleich nutzen, aber einige Stunden später was schon ein Techniker da und hat das Problem behoben 👍 Die Lage ist super, viele Sehenswürdigkeiten sind schnell erreichbar. Wir hatten leider viele Moskitos, aber das ist ein natürliches Vorkommnis 😃 Die Waschmaschine war sehr praktisch besonders wenn man länger auf Reisen ist 👍 Vielen Dank für den tollen Aufenthalt

Casa Anna
Il soggiorno a casa di Annalisa stato fenomenale, lei è stata così carina da venirci a prendere alla stazione con l'auto, anche se la casa dista soli 15 minuti a piedi dalla stazione. La sua gentilezza, accoglienza e ospitalità sono stati preziosi, ci hanno fatto sentire a casa. Tutto funzionava in casa, abbiamo usato la cucina, la terrazza e internet. Ci ha fatto trovare anche un ventilatore, anche se la casa era fresca. Ci ha dato informazioni sui ristoranti vicini da raggiungere fra cui uno buonissimo, LA PISTA, dove lavora anche lei e dove ti trattano come papi. La casa è una bomboniera, tutta fiocchetti e lenzuola pulite e candide. Lei cura ogni minimo particolare e si vede. Conosce l'arte di accogliere e ci mette il cuore. Utilissime le informazioni su come raggiungere la magnifica Certaldo Alta con la funicolare, panorama mozzafiato. Il letto era comodo e il bagno pulitissimo. Che chiedere di più? Un posto dove andare per staccare dalla città e ricaricare le pile. Grazie!!!
Quick stats about house rentals in Poggibonsi
Total rentals
10 properties
Nightly prices starting at
$77 SGD before taxes and fees
Total number of reviews
270 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Coop, Pam Barberino Val D'Elsa and Centro Commerciale Valdelsa
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Spiaggia Libera
- Teatro Verdi
- Palazzo Vecchio