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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Poggibonsi

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Pool

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (80)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Property grounds

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (107)
"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Your panoramic house in Tuscany between vineyards and olive groves.
Exterior

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (39)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Relais Badia a Passignano
Land view from property

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Exclusive Farmhouse Pool & View of San Gimignano
Outdoor dining

Exclusive Farmhouse Pool & View of San Gimignano

10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Pool

Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14

9.8 out of 10, Exceptional, (7)
"My family and I stayed here for almost a full week in the spring, and had an amazing time. The host was extremely responsive about the check-in process leading up to the stay, during the stay whenever we had any issues, and even after our stay when we needed to recover an item that was left behind. There were some slight hiccups with the house during our stay (garage door opener was out of batteries one time and the shower drain clogged one time), but the host was proactive as can be and quick...
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Property grounds

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

10.0 out of 10, Exceptional, (54)
"Nice house with a beautiful pool , well located to visit Tuscany. "
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
The timeless elegance with private pool
Outdoor pool

The timeless elegance with private pool

10.0 out of 10, Exceptional, (1)
"The villa has great charm and character, a huge living room where you can spend time with friends, as well as outdoor spaces and the swimming pool. It is an excellent point to visit San Gimignano Colle val d'elsa Florence and Siena. Thanks Luca for hosting us"
The timeless elegance with private pool
Macinella Friendly and Artistic apartment "Sunflower 1"
Exterior

Macinella Friendly and Artistic apartment "Sunflower 1"

9.0 out of 10, Wonderful, (22)
"Traditional accommodation in a great location. In the middle of the sweet Tuscan hills. Very nice property, ambience Italian warmth and great atmosphere. always gladly again..."
Macinella Friendly and Artistic apartment "Sunflower 1"
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Property grounds

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

10.0 out of 10, Exceptional, (5)
"Amazing location with everything you need for a relaxing and pleasant stay! Uncomplicated check-in and check-out, fast replies to any questions. Thanks a lot Arianna and Natale!"
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Villa 'Beccalorzo' with Private Pool, Wi-Fi and Air Conditioning
Exterior

Villa 'Beccalorzo' with Private Pool, Wi-Fi and Air Conditioning

10.0 out of 10, Exceptional, (1)
"Absolutely stunning. Every detail was taken care of. This home and property exceeded what you see in the photos. "
Villa 'Beccalorzo' with Private Pool, Wi-Fi and Air Conditioning
Villa Zambra by MMega
Outdoor dining

Villa Zambra by MMega

10.0 out of 10, Exceptional, (1)
"Beautiful villa in an ancient tower! Immaculate and beautifully furnished Easy commute to Tuscany points of interest"
Villa Zambra by MMega
Vintage 70s Home - your place in Tuscany. Holiday Home, Events & Retreats.
Property grounds

Vintage 70s Home - your place in Tuscany. Holiday Home, Events & Retreats.

10.0 out of 10, Exceptional, (4)
"What an experience it was staying in the 70s vintage home. Natalie and Lorenzo were the best hosts we have ever had- such wonderful people who helped us out with everything we needed. The home was perfect- safe for our toddler and with the best views and very well kitted out. We enjoyed that we could walk into the village. We highly recommend this place!!"
Vintage 70s Home - your place in Tuscany. Holiday Home, Events & Retreats.
Entire Tuscan farmhouse with private pool between Siena and Florence
Outdoor dining

Entire Tuscan farmhouse with private pool between Siena and Florence

10.0 out of 10, Exceptional, (3)
"We had a wonderful visit to the area and loved the home and property. The check-in and departure was very easy. We had many questions before our arrival and every time we received a prompt reply"
Entire Tuscan farmhouse with private pool between Siena and Florence
Casabianca 12, Emma Villas
Pool

Casabianca 12, Emma Villas

10.0 out of 10, Exceptional, (1)
"The views from the property are just as shown in the pictures. The home is at the top of a hill, so the views are absolutely beautiful and scenic. One of the main reasons we rented was because of the stone kitchen and it was even better than pictured. The owner was kind enough to leave us pasta which certainly helped on the first night. Looking forward to renting there again soon."
Casabianca 12, Emma Villas
private Villa with A/C, Wifi, Swimming Pool in the heart of Chianti (Tuscany)
Exterior

private Villa with A/C, Wifi, Swimming Pool in the heart of Chianti (Tuscany)

9.0 out of 10, Wonderful, (2)
"This is a great home with all the amenities a traveling family cares to have. The owners were very helpful during our stay and helped make the trip more memorable! Highly recommend this if you want to stay in a real Tuscan villa that’s been modernized to enhance your stay!"
private Villa with A/C, Wifi, Swimming Pool in the heart of Chianti (Tuscany)
Villa with private pool overlooking San Gimignano. Exclusive use of the property
Pool

Villa with private pool overlooking San Gimignano. Exclusive use of the property

10.0 out of 10, Exceptional, (20)
"Great place, fantastic house with good swimming pool and a terrace on wich you can have diner overlooking the landscape and SanGimignano on the hill and admire the tramonto ‘"
Villa with private pool overlooking San Gimignano. Exclusive use of the property
Relais Badia a Passignano - Merlot Apartment
Exterior

Relais Badia a Passignano - Merlot Apartment

Relais Badia a Passignano - Merlot Apartment
Idyllic Countryside Retreat with Rustic Elegance
Exterior

Idyllic Countryside Retreat with Rustic Elegance

10.0 out of 10, Exceptional, (2)
"The pictures do not do this place justice. The pool and pool house are incredible for lunch gatherings the design of the pool is the best we’ve ever had. Each room has AC unit and all appliances are top of the line. Rooms are spacious and bathrooms are old worldly but top class. Emanuele met us at the property and showed us around. And was available for questions by phone. We can not speak highly enough of this home!!"
Idyllic Countryside Retreat with Rustic Elegance
Villa Vianci RBO, your home away in Tuscany
Outdoor dining

Villa Vianci RBO, your home away in Tuscany

10.0 out of 10, Exceptional, (1)
"Friends and family gathered at this wonderful villa in Tuscany for a week in September. Everything about this place is extraordinary. Incredible vistas & sunsets. Magnificent home with beautiful furnishings. I cannot recommend this place enough."
Villa Vianci RBO, your home away in 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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Frequently asked questions

How much do villas in Poggibonsi cost?
Villas in Poggibonsi range between and per night. These stays offer the privacy to enjoy your own space at a price that's gentle to your wallet. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Poggibonsi?
Poggibonsi has 102 villas to pick from. Find a stay that's right for you quickly and easily by checking the "Villa" box under the "Property type" tab in our filter tool.
What is there to do near my villa in Poggibonsi?
Poggibonsi has enough sights and activities to keep you amused for weeks (or months!), starting with Tenuta Torciano Winery. Monteriggioni Castle, Isole e Olena Winery and Sovestro in Poggio Winery are other renowned attractions. If you're sticking around a while, Castello di Monsanto and Buondonno Winery will add the finishing touches to your itinerary.