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Our top choices for Poggibonsi villas
1. Rooster House, Cooking Classes, and Opera
Rooster House, Cooking Classes, and OperaTavarnelle Val di Pesa
The price is NZ$249
includes taxes & fees
9 Nov - 10 Nov
2. Villa Montecastello
Villa MontecastelloMonteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
Alvaro
The price is NZ$638
includes taxes & fees
21 Nov - 22 Nov
3. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Villa in the Heart of Chianti — Peace, Views, and Authentic TuscanyCertaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
Kelly C.
The price is NZ$2,337
includes taxes & fees
9 Nov - 10 Nov
4. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36Colle Val D'Elsa
The price is NZ$23,720
includes taxes & fees
29 Nov - 30 Nov
5. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Villa 'La Petrosa' with Private Pool, Private Garden and BalconyRadda in Chianti
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
JIm B.
The price is NZ$2,167
includes taxes & fees
10 Nov - 11 Nov
6. "A Casa di Franca Villa con piscina"
"A Casa di Franca Villa con piscina"Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Anonymous traveller
The price is NZ$3,070
includes taxes & fees
9 Nov - 10 Nov
7. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 GuestsMontespertoli
The price is NZ$12,069
includes taxes & fees
15 Nov - 16 Nov
8. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
Ron M.
The price is NZ$15,237
includes taxes & fees
9 Nov - 10 Nov
9. Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa Milani with Shared Pool, Private Terrace & Wi-FiMontespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
Scott M.
The price is NZ$3,260
includes taxes & fees
9 Nov - 10 Nov
10. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suitesMontespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
Krista G.
The price is NZ$2,768
includes taxes & fees
29 Nov - 30 Nov
11. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,AircoMontespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
Elise D.
The price is NZ$2,732
includes taxes & fees
9 Dec - 10 Dec
12. Exclusive Estate | Personal Concierge & Heated Pool
Exclusive Estate | Personal Concierge & Heated Poolimpruneta
10.0 out of 10, Exceptional, (117 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Oli P.
The price is NZ$2,495
includes taxes & fees
9 Nov - 10 Nov
13. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37Firenze
The price is NZ$28,464
includes taxes & fees
9 Nov - 10 Nov
14. Villa Mami: A Tuscan retreat full of elegance and charm
Villa Mami: A Tuscan retreat full of elegance and charmToscana
10.0 out of 10, Exceptional, (1 review)
The price is NZ$5,096
includes taxes & fees
9 Nov - 10 Nov
15. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-FiGaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
Bernard K.
The price is NZ$3,124
includes taxes & fees
15 Nov - 16 Nov
16. Villa Capanna: A Window onto Tuscany
Villa Capanna: A Window onto TuscanyVico dʼArbia
The price is NZ$2,991
includes taxes & fees
9 Nov - 10 Nov
17. Villa Torre Among the Hills of Siena
Villa Torre Among the Hills of SienaVico dʼArbia
The price is NZ$2,991
includes taxes & fees
10 Nov - 11 Nov
18. Golden Hour - Wedding in Florence
Golden Hour - Wedding in FlorenceToscana
The price is NZ$5,874
includes taxes & fees
10 Nov - 11 Nov
19. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, JacuzziRignano sull'Arno
The price is NZ$9,787
includes taxes & fees
10 Nov - 11 Nov
20. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of TuscanyVaggio
The price is NZ$2,084
includes taxes & fees
9 Nov - 10 Nov
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Learn more about Poggibonsi
Medieval towers and historic buildings surround Poggibonsi's charming Piazza Cavour, where locals gather at outdoor cafés serving Tuscan specialities. Climb to Poggio Imperiale fortress for panoramic views, then visit nearby San Gimignano's famous towers or Siena's magnificent Piazza del Campo.
