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Compare 103 Vacation Homes in Poggibonsi with updated reviews, rates, and availability.

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Casa Pineta

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany

9.6 out of 10, Exceptional, (46)
"The villa was a fantastic opportunity to get away from the hustle of city life. The local town was old world and friendly. The restaurant, La Toppa, was amazing. The owner of the restaurant & villa ands his family was very friendly, responsive and helpful. Wonderful stay in Tuscany. "
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Chianti Craft House Badia a Passignano
Point of interest

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"The apartment is at the heart of the small village, central to several great restaurants and practically across the street from the incredible 11th century abbey. The place was very clean and has been recently renovated, but still had a very historic feel to it. Emanuel, our host, was very friendly and gracious. He offered several personal recommendations to restaurants and a wine tasting at a nearby castle, all of which were great! Would definitely stay here again!"
The price is SAR 645
SAR 891 total
includes taxes & fees
31 Jan - 1 February 2025
Chianti Craft House Badia a Passignano
San Gimignano: ancient house renovated in the heart of San Gimignano
Interior

San Gimignano: ancient house renovated in the heart of San Gimignano

9.0 out of 10, Wonderful, (2)
"ancient Town. beautiful vistas, very interesting place......good for 2 couples or couple with children only issue was could not get warm water in shower this was brought to attention of manager when we left .....Concetta was very kind and was an immense help with our late check in"
San Gimignano: ancient house renovated in the heart of San Gimignano
Medieval 11-story tower, 143 steps, with dreamy top terrace
Outdoor dining

Medieval 11-story tower, 143 steps, with dreamy top terrace

10.0 out of 10, Exceptional, (4)
"We had such a wonderful stay. The views from the rooftop are incredible. Very private and a lovely way to enjoy sunset, sunrise and the views of the town and countryside. The host is lovely and was very accommodating."
The price is SAR 1,563
SAR 2,013 total
includes taxes & fees
31 Jan - 1 February 2025
Medieval 11-story tower, 143 steps, with dreamy top terrace
Vedi Torre by Interhome
Pool Outdoor

Vedi Torre by Interhome

9.6 out of 10, Exceptional, (7)
"This is a very nice home with a pool overlooking Tuscany. The sunsets are beautiful. The accommodations were comfortable. The check in process was very brief. Despite asking for help many times with the WiFi and stove issues, we did not get resolution. The host was very brief and seemed too busy to assist us. Despite this, we enjoyed our stay in this beautiful villa. It was fantastic for our large group of 9."
Vedi Torre by Interhome
Tusci Loft San Gimignano - Un Piccolo Gioiello nel Città
Living area

Tusci Loft San Gimignano - Un Piccolo Gioiello nel Città

9.8 out of 10, Exceptional, (9)
"Lovely Tuscan countryside views visible in the distance from our apartment windows! Very tastefully decorated. We had a nice comfortable stay overall. Still fresh from reno as in the photos but showing some wear and in need of a bit of maintenance and attention to updating some instructions and soft furnishings. No dryer instructions though every other appliance instructions were available. Parking and the grocery store is available at the opposite end so be prepared to walk at least 10-15...
Tusci Loft San Gimignano - Un Piccolo Gioiello nel Città
Betulla C, San Gimignano, Italy
Aerial view

Betulla C, San Gimignano, Italy

10.0 out of 10, Exceptional, (3)
"Wir haben eine wundervolle Woche in Betulla C verbracht. Die Wohnung war sehr sauber und es ist alles vorhanden was man im Urlaub benötigt. Das parkähnliche Grundstück und der Pool sind sehr gepflegt. Vom Grundstück aus hat man außergewöhnlich schöne Aussichten. Organisation und Schlüsselübergabe waren perfekt. Wir können die Unterkunft gerne weiterempfehlen und würden diese auch bei einem nächsten Toskana- Urlaub wieder buchen."
Betulla C, San Gimignano, Italy
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Terrace/patio

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
2 bedroom accommodation in San Gimignano
outside

2 bedroom accommodation in San Gimignano

10.0 out of 10, Exceptional, (1)
2 bedroom accommodation in San Gimignano
"VILLA DONELLA" a corner of Tuscany history, just minutes from San Gimignano
Exterior

"VILLA DONELLA" a corner of Tuscany history, just minutes from San Gimignano

9.4 out of 10, Exceptional, (9)
"Charming apartment with good outside space and private parking. Cristina and Claudia are lovely and very helpful. Quite near a main road which although can be noisy during the day, is quiet at night. PAM supermarket just up the road as is petrol station. Need to drive into Poggibonsi, too far to walk. Easy train journey to both Florence and Siena. San Giminagno is about 10 minutes drive. apartment well placed for exploring the area. Easy drive from Pisa Airport. Would definitely recommend."
"VILLA DONELLA" a corner of Tuscany history, just minutes from San Gimignano
holiday home "Under the walls of Leonardo"
Room

holiday home "Under the walls of Leonardo"

8.6 out of 10, Excellent, (4)
"I would recommend this property to anybody who is interested there is everything I needed there"
The price is SAR 313
SAR 508 total
includes taxes & fees
31 Jan - 1 February 2025
holiday home "Under the walls of Leonardo"
Holiday Home 'Casa Ernesto - Porzione Di Colonica' with Private Garden and Wi-Fi
Outdoor dining

Holiday Home 'Casa Ernesto - Porzione Di Colonica' with Private Garden and Wi-Fi

10.0 out of 10, Exceptional, (2)
Holiday Home 'Casa Ernesto - Porzione Di Colonica' with Private Garden and Wi-Fi
THE CASINA OF SANT 'AGOSTINO
Private kitchen

THE CASINA OF SANT 'AGOSTINO

The price is SAR 293
SAR 419 total
includes taxes & fees
7 Jan - 8 January 2025
THE CASINA OF SANT 'AGOSTINO
The Photographer's House
Living area

The Photographer's House

9.8 out of 10, Exceptional, (9)
"The house is spacious, interesting and has everything needed for a holiday. The garden is a huge bonus - room to relax with a view (and grapes on the vine!). It was a joy to stay in an historic house in such an interesting town, with shops and restaurants within easy walking distance. We had a delicious meal at the owner’s restaurant too."
The Photographer's House
House with garden
Terrace / Balcony

House with garden

10.0 out of 10, Exceptional, (23)
"Nous avons passé un excellent séjour ! La maison est spacieuse et très confortable, il ne manque rien. Malgré la chaleur, elle reste relativement fraîche. Nous avons particulièrement apprécié la magnifique terrasse, fleurie, qui donne sur un très grand jardin, sans aucun vis à vis. L'endroit est très calme. La piscine, commune à la résidence, est grande et splendide, et il n'y avait pas beaucoup de monde, c'était très agréable. La maison est parfaitement située et nous a permis de sillonner...
House with garden
3 bedroom accommodation in Poggibonsi SI
area

3 bedroom accommodation in Poggibonsi SI

7.0 out of 10, Good, (2)
"Propriété bien distribuée dans un cadre champêtre très agréable Appartement spacieux avec de nombreuses baies vitrées donnant sur des terrasses. Attention chemin d’accès non goudronné avec de nombreuses ornières."
3 bedroom accommodation in Poggibonsi SI
CASAILCAMBIO Typical Tuscan hut recently renovated, about 45 square meters.
Room

CASAILCAMBIO Typical Tuscan hut recently renovated, about 45 square meters.

CASAILCAMBIO Typical Tuscan hut recently renovated, about 45 square meters.
4 bedroom accommodation in San Donato in P. FI
pool

4 bedroom accommodation in San Donato in P. FI

10.0 out of 10, Exceptional, (2)
"This is a wonderful house in a perfect location for touring Chianti and making day trips to Siena Florence and Lucca. The house is a short distance to the sublime little town of San Donato with great restaurants there or nearby"
4 bedroom accommodation in San Donato in P. FI
Vrbo Property
Living area

Vrbo Property

10.0 out of 10, Exceptional, (2)
"My daughter and I stayed for five days. The house was lovely and the setting was gorgeous. Very close to San Gimignano and to local winery Pieterserena Arrigoni."
Vrbo Property
Granaio - Il Casale di Villore, Poggibonsi, Siena, Tuscany
Outdoor dining

Granaio - Il Casale di Villore, Poggibonsi, Siena, Tuscany

10.0 out of 10, Exceptional, (34)
"Look no further!! BOOK THIS PLACE NOW!! Absolutely amazing stay! Beautiful Villa with a stunning view. Very comfortable and charming. Spacious, peaceful and quiet. Bed is comfortable, ample space for our suitcases, bathroom is large. Located among the rolling hills of Tuscany. Stay like a local! Antonio was very kind. Would absolutely stay here again."
Granaio - Il Casale di Villore, Poggibonsi, Siena, Tuscany
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.
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Other property types in Poggibonsi

Podere il Pino
Property grounds

Podere il Pino

9.2 out of 10, Wonderful, (13)
"Let’s start with the good: lots of communication and the lady was very kind and helpful. Beautiful views and peaceful. It was nice to look out and see green EVERYWHERE!! The perfect place to relax. The pool is so refreshing and clean. Our kids didn’t leave it. Ok. We didn’t either lol. Grapevine lined pergolas. I mean, OMG! How cute! Now, for some things to work on that round make this place better: I understand a lot of places around Italy don’t do air conditioning, so we had to keep the...
Podere il Pino
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Interior

SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI

10.0 out of 10, Exceptional, (5)
"Rented the property for a birthday celebration, it was great! There were anywhere from 10 to 14 people every day, there is plenty of room for all of us. The pool was fantastic. We were able to spend time together, but had privacy if we wanted it the property manager and owners were extremely responsive to all questions and requests. It was the perfect location in Tuscany thoroughly enjoyed ourselves. Thank you so much!!"
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Nice apartment in villa with pool, WIFI, TV, patio, panoramic view, parking, close to San Gimignano
Appartamento Ginestra

Nice apartment in villa with pool, WIFI, TV, patio, panoramic view, parking, close to San Gimignano

10.0 out of 10, Exceptional, (5)
"Très bon sejour"
Nice apartment in villa with pool, WIFI, TV, patio, panoramic view, parking, close to San Gimignano
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.