
Villa holiday rentals in Poggibonsi
Find and book unique villas on Airbnb
Top-rated villa rentals in Poggibonsi
Guests agree: these villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for villa rentals in Poggibonsi
Private villa rentals

Villa Via Francigena
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.

Charming villa 15' walk to center stunning view
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.

Casanova of Bricciano
What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.

La Cipresseta Estate | Cipresso House
Really nice place. Sweet and super helpful hostess. We are coming back

Charming poolside house
We will definitely come back!

La Macina Farmhouse And Olive Oil Estate
We stayed at La Macina Farmhouse for ten nights in October 2024. The photos do not not truly capture how special this 16th century villa is, it is magical. There were days we did not leave the villa as it had everything we could want or need and was such a nice retreat from the cities we visited in the surrounding region. It is perfectly located in the hills above Lucca, day trips to Firenze, Sienna, Pisa, Carrara, Forte di Marmi and Parma are easy to drive to for daily adventures. The restaurants in the surrounding hills were incredible with great menus at very reasonable prices. I highly recommend this property and Lucca Apartments & Villas for their exceptional service.

Montemarcoli
We had an amazing stay at the villa. A modern house in a quiet environment with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.

Luxury villa in Tuscany Panzano in Chianti
Unbelievable! The views were breathtaking, the villa was stunning, all in all a perfect Tuscan experience
Luxury villa rentals

Luxury Villa on Chianti Wine Estate
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.

Casa Bianca, a gorgeous Tuscan home in Crete Senesi
Photos do not do justice to the amazing views. Very special place.

Valluccia 51
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.

villa "La Fonticina"
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.

Romantic Villa with private pool and fabulous view
Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!

Beautiful tuscan country house
The house is beautiful and very big. It is located just outside of Buonconvento and offers complete privacy. A car is an advantage. The rooms are spacious, there are mosquito nets above all beds and enough bathrooms and toilets for everyone. In general, the house is very well equipped, both in the kitchen and otherwise. The pool is slightly elevated, beautiful, large, with natural shade all around and offers a magnificent view on the surrounding countryside. In the huge garden you can eat, linger, play... There is even a small basketball court. But beware: right next door there are wild blackberries and the ball can be lost :) In Buonconvento there is a coop, a fine gelateria and a good coffee with the famous and fine products of Le Dolcezze di Nanni. For a good pizza, the drive to the Mulinum restaurant is worth it a little outside, they have their own mill and process their own grain. We highly recommend the house.

Villa with garden. The Cardinal's Garden.
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.

Podere La Casetta - 2 People - Private Pool
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.
Villa rentals with a pool

Villa Gelsomino, your dream in Tuscany
The villa was perfection for the 5 of us, from the space to the amenities- football field, pool, gym, bbq pit, it was great for an adult family with varied interests. The service was so warm and non intrusive, its evident Jerose and Anita take such pride in maintaining a high standard and are always working, whilst keeping a professional distance. Thank you for making this trip so memorable and wonderful. We will be back!

Bellagatta, an Enchanting spot in Val d'Orcia
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!

Luxury Tuscany Villa on the hill with private pool
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!

Lilium,delux farmhouse in the chianti hills
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.

Romantic Villa with private pool - "Il Pollaio"
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!

The twigs
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. 🙏

Unique Villa in Tuscany
A stunning property, completely private and quiet. Large outdoor heated pool was well maintained with perfect outdoor eating and sitting areas. We ate out on the terrace every night. Luc recommended the closest Osteria which we all loved, and also recommended the spot to see those iconic views of Tuscany with the avenues of cypress trees. All 6 of us had joyful experience. Highly recommended.

la Balza
Wonderful farmhouse and experience! Very peaceful! Alessandro invited us to a dinner/wine tasting at his family vineyard. Great and delicious experience! Thanks Alessandro!
Destinations to explore
- House rentals Poggibonsi
- Family-friendly rentals Poggibonsi
- Pet-friendly rentals Poggibonsi
- Rentals with a patio Poggibonsi
- Flat rentals Poggibonsi
- Apartment rentals Poggibonsi
- Rentals with a washing machine and dryer Poggibonsi
- Rentals with outdoor seating Poggibonsi
- Rentals with pools Poggibonsi
- Villa rentals Province of Siena
- Villa rentals Tuscany
- Villa rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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