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Villa holiday rentals in Poggibonsi

Find and book unique villas on Airbnb

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Popular amenities for Poggibonsi villa rentals

Private villa rentals

Guest favourite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

JasminRating, 5 stars3 weeks ago
Wir haben uns sehr wohl gefühlt bei Beatrice und Alessandro. Es ist ein wunderbarer Ort um Urlaub zumachen! Wir werden definitiv wieder kommen!
Top Guest favourite
Villa in Centro Storico
5 out of 5 average rating, 40 reviews

Charming villa 15' walk to center stunning view

ChristineRating, 5 stars2 days ago
Wonderful villa with a beautiful outdoor area- fruit trees, roses, and flowers. We enjoyed the wine, snacks and fresh fruit the host had for us upon arrival. This was our last stop in Italy. Bedding, mattresses and AC has not been great in the places that we have stayed, and never was there a fan. This villa had a comfortable bed , great ac, and a ceiling fan in the bedroom. My husband said his best night sleep the entire trip. We were missing our dogs and cats and we loved having theirs visit us daily! The hosts were traveling so we didn’t get the chance to meet them. They regularly checked in on us to make sure everything was good and provided local recommendations. Given the reviews and accommodation, I’m sure they are amazing! If you’re ever in Florence, this place is worth the stay.
Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova di Bricciano

JacquesRating, 5 stars1 month ago
Nous avons découvert un endroit incroyable avec une vue et un décor fééerique typiquement de la Toscane. Les hôtes Andréa et Fabio sont très accueillants et disponibles, et la maison était impéccable et identique aux photos. C'est plus qu'un 5 étoiles! Nous sommes des fervents de la location par AIrbnb, et ce fut le plus bel endroit que nous avons connu, un coup de coeur! Nous avons pu également profiter d'une dégustation de vin à leur vignoble familial, et ce fut une très belle et enrichissante expérience. Nous avons passé des moments mémorables en Toscane et c'est beaucoup à cause de cette location. De plus, il y a un petit village à proximité, et nous avons découvert de délicieux restaurants. Cette villa est également près de Florence et Sienne. Nous vous recommandons très fortement cet endroit.
Guest favourite
Villa in Asciano
4.93 out of 5 average rating, 88 reviews

Casa Bianca gorgeous Tuscan home, Crete Senesi

Johannes KarlRating, 5 stars6 days ago
Entspannend, angenehmer Aufenthalt mit toller Aussicht, schön angelegtem Garten und nicht zu weit von Siena entfernt
Superhost
Villa in Poggibonsi
4.79 out of 5 average rating, 70 reviews

Charming poolside house

AndreasRating, 5 stars6 days ago
Sehr schöne Wohnung auf dem Land. Tolle Aussicht vom Pool. Gemütliche Sitzmöglichkeiten auf der großen Terrasse. Wir haben uns sehr wohl gefühlt.
Top Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars2 weeks ago
Vi hadde et fantastisk opphold i villaen. Et moderne hus i rolige omgivelser med vakker utsikt. Brigitta var svært hjelpsom og svarte raskt på våre henvendelser både før og under oppholdet.
Top Guest favourite
Villa in San Leolino
4.99 out of 5 average rating, 109 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

ElkeRating, 5 stars1 week ago
Unser Aufenthalt bei Marta und ihrer Familie hätte schöner nicht sein können. Wir haben uns vom ersten Moment absolut wohl gefühlt. Das Anwesen ist absolut weitläufig, liebevoll ausgestattet, unglaublich toll gepflegt und mit Liebe geführt. Marta und Ihre Familie sind absolut liebenswert und kümmern sich ganz reizend um ihre Gäste. Es werden einem alle Wünsche erfüllt. Der Pizza-Abend war ganz wunderbar und für uns ein gelungener Abschluss unseres Aufenthaltes. Wer traumhaftes, abgelegenes toskanisches Ambiente und liebevolle Gastgeber sucht ist in "Poggio del Fattore" genau richtig.
Superhost
Villa in Colle di Val d'Elsa
4.89 out of 5 average rating, 27 reviews

Villa l'elsa beautiful country home with view - vi

MichaelRating, 5 stars2 weeks ago
Incredible Tuscan villa with the best owners and rental group. We had a family of 9 including a baby and the house was exactly what we needed - very spacious, accommodating owners, beautiful views, and a perfect location for visits to wineries and other tourist attraction cities. Irida was very responsive if we had any issues, and Francesca catered to our every need throughout our week stay. Upon arrival, Irida was there to give us a tour of the house and get us all set up with everything we would need for the baby etc. It was a level of service we hadn’t ever experienced with Airbnb! The house itself is beautiful as well, we loved sitting on the patio and greatly enjoyed the pool. Best of Mas set up many experiences for our group - welcome dinner & cooking class, private tours & transfers, wine tastings, lunch/dinner reservations, you name it they took care of it. Our group had the vacation of a lifetime thanks to Best of Mas with this rental property and the experiences they provided

Luxury villa rentals

Top Guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Top Guest favourite
Villa in Barberino Tavarnelle
5 out of 5 average rating, 36 reviews

Valluccia 51

FlorisRating, 5 stars1 month ago
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.
Top Guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 15 reviews

villa "La Fonticina"

KathyRating, 5 stars1 week ago
Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 125 reviews

Villa a Montepulciano con Piscina

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Top Guest favourite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa con giardino. Il Giardino del Cardinale.

ShaneRating, 5 stars3 weeks ago
Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.
Guest favourite
Villa in Greve in Chianti
4.93 out of 5 average rating, 27 reviews

Luxury villa in Tuscany Panzano in Chianti

KatieRating, 5 stars1 month ago
Unbelievable! The views were breathtaking, the villa was stunning, all in all a perfect Tuscan experience
Top Guest favourite
Villa in Cavriglia
4.99 out of 5 average rating, 133 reviews

Villa Poggio a Mandria in Chianti

VaughnRating, 5 stars2 weeks ago
A beautiful place, beautiful surroundings, great hosts, great pool, just everything was perfect. Didn’t want to leave. Felt like home and couldn’t wait to get back there on the days we ventured out.
Guest favourite
Villa in Lastra a Signa
4.98 out of 5 average rating, 62 reviews

"La Falterona" Villa 15 km Florence

ChristopherRating, 5 stars2 weeks ago
We were a group of 10, 5 couples. I think I speak for everyone when I say our stay was the ultimate, authentic Tuscan experience. The Villa had plenty of areas to have the group all together to eat , drink and generally just enjoy life!. We were also blessed with perfect weather so we could take full advantage of the outdoor spaces as well. The highlight had to be our cooking class Domizio arranged with local chef Luciano Piacenza. He is a remarkable chef, incredibly knowledgeable and detail oriented with an amazing flair for teaching and making it so much fun for all. Lucian also created an amazing Tuscan meal on the evening of our arrival that will go down as the best chicken I have ever eaten. If you are looking for this experience, book it now and just count the days because it will be the trip of a lifetime.

Villa rentals with a pool

Guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 19 reviews

Villa Gelsomino, your dream in Tuscany

LenaRating, 5 stars2 months ago
Wir waren mit einer Gruppen von 4 Paaren und drei Kleinkindern unterwegs. Und hat die Unterkunft super gefallen. Jedes Paar hatte sein eigenes Badezimmer und alles war super sauber. Die gesamte Anlage war sehr gepflegt. Es gab einen Tennisplatz, einen Fußballplatz, Kicker, Volleyball und einen tollen Kinderspielplatz. Besser ausgestattet kann die Anlage nicht sein. Zudem ist die Lage der Unterkunft perfekt um die Toskana zu erkunden. Wir waren rundum zufrieden und würden sofort wiederkommen.
Guest favourite
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Guest favourite
Villa in Castiglione d'Orcia
4.97 out of 5 average rating, 118 reviews

Wp Relais Borgo Vignalunga

SumeRating, 5 stars1 week ago
We had a lovely stay — the villa is absolutely beautiful and we had a great time enjoying the space and surroundings. The location is also ideal, close to stunning towns like Pienza. A few improvement points: there was no proper coffee-making equipment, just a few filters; the fireplace hadn’t been cleaned and had no firelighters; and the air conditioning didn’t work in about half the rooms. Also, the check-in wasn’t smooth — the time was moved to 16:00, but the cleaners were still busy when all 14 of us arrived. With a bit more attention to these details, it could be a truly exceptional stay.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 25 reviews

Luxury Tuscany Villa on the hill with private pool

EmmaRating, 5 stars3 weeks ago
We booked this for a girls holiday and we had the best week. We didn’t hire a car, we walked to a few of neighbouring towns and got a taxi to Lucca, and a train to Florence one day. Neighbouring towns have small supermarkets and the walks to them were enjoyable, the scenery is truly incredible. Lucca is beautiful and has incredible markets, it’s a must see if you stay here. The villa itself is exactly as shown in the pictures, the pool area is gorgeous, we sat around the table every night for dinner, and when it’s dark there’s clusters of fireflies sparkling in the roses, it was magical. Stefania was great, very responsive and there if we needed her. We’d definitely recommend and book this villa again in the future!
Guest favourite
Villa in San Gimignano
4.88 out of 5 average rating, 72 reviews

Lilium,delux farmhouse in the chianti hills

CharlotteRating, 5 stars2 weeks ago
We had a fantastic stay at Concetta's beautiful home! The house itself is gorgeous and traditionally Tuscan. It is also in the most incredible scenery and sitting outside and taking in the view was an absolute joy. However, by far the best thing about our stay was Concetta and her husband Paolo. They could not have done more to make us feel more at home and it honestly felt like we were part of the family while we were there (including making us the most incredible meal, which I would strongly recommend you do if you stay!) Their hospitality, helpfulness and warmth made it feel like a true escape and I could not recommend it more.
Top Guest favourite
Villa in Volterra
5 out of 5 average rating, 24 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars3 weeks ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Guest favourite
Villa in Buonconvento
5 out of 5 average rating, 11 reviews

Beautiful tuscan country house

LukasRating, 5 stars1 month ago
Das Haus ist schön und sehr gross. Es liegt etwas ausserhalb von Buonconvento und bietet absolute Privatsphäre. Ein Auto ist von Vorteil. Die Zimmer sind grosszügig, es gibt Mückennetze über allen Betten und genügend Badezimmer und WCs für alle. Generell ist das Haus sehr gut ausgestattet, sowohl in der Küche als auch sonst. Der Pool ist etwas erhöht, schön, gross, mit natürlichem Schatten rundherum und bietet eine herrliche Aussicht auf die umliegende Landschaft. Im riesigen Garten kann man Essen, Verweilen, Spielen... Es gibt sogar einen kleinen Basketball-Court. Aber Achtung: Gleich nebenan gibt es wilde Brombeeren und der Ball kann verloren gehen :) In Buonconvento gibt es einen Coop, eine feine Gelateria und eine gutes Caffé mit den berühmten und feinen Produkten von Le Dolcezze di Nanni. Für eine gute Pizza lohnt sich die Fahrt ins Restaurant Mulinum etwas ausserhalb, sie haben eine eigene Mühle und verarbeiten ihr eigenes Getreide. Wir können das Haus sehr empfehlen.
Top Guest favourite
Villa in Sinalunga
5 out of 5 average rating, 44 reviews

Gli sterpi

NatalieRating, 5 stars2 weeks ago
Sandrine’s Airbnb was by far the best accommodation we’ve ever experienced—a peaceful paradise nestled in the hills of Tuscany. What made it truly unforgettable, though, was the incredible generosity of our hosts. Sandrine welcomed us with a warm smile and thoughtfully provided delicious food and drink throughout our stay. She also shared wonderful recommendations for places to visit and things to see. It was a true blessing to meet such kindhearted and gracious people. 🙏

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Poggibonsi
  6. Villa rentals