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Featured Villas in Poggibonsi

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor pool
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
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, (32)
"Lovely property, very comfortable. Good location to explore Tuscany. There is an excellent supermarket less than 10 minutes away. Families would be very comfortable here."
Your panoramic house in Tuscany between vineyards and olive groves.
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, (46)
"This place exceeded all of our expectations. The host and his family were amazing and very accommodated. Perfect size for two couples. Bedrooms and bathrooms were private. The location was perfect. We were able to take daily trips everywhere in Tuscany between 15 minutes and one hour. The house and pool were even better than the pictures portray. The place came stocked with everything you need For your vacation. If ever back in Tuscany I would definitely stay here again."
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Macinella Friendly and Artistic apartment "Sunflower 1"
Pool
Macinella Friendly and Artistic apartment "Sunflower 1"
9.0 out of 10, Wonderful, (21)
"I rated as a 4 instead of 5 for two reasons. 1) the beds were fine but could have been better. (2) the drive on gravel roads were a bit iffy when it rained. Stelio and the rest of the group were very friendly and responsive and the views were amazing . If you walk across the road you can see San Gimignano which was very cool. Also convenient to many of the towns."
Macinella Friendly and Artistic apartment "Sunflower 1"
Entire Tuscan farmhouse with private pool between Siena and Florence
Outdoor pool
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
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, (73)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Outdoor pool
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
10.0 out of 10, Exceptional, (98)
"The entire experience (pre-booking, booking, and our stay) was positive. Barbara quickly responded to my inquiries before and after booking and greeted us upon arrival. Plus, she prepared two delicious meals for our group that we enjoyed at the outside dining area—from which we had gorgeous views of the San Gimignano skyline. There are uninterrupted views of San Gimignano from inside, too: from the kitchen, the living room, and one of the bedrooms. We savored those views our entire stay. The...
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
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)
"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
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)
"The villa is beautiful and homey and well stocked — and Simon, Pham and Aliah were the most helpful and generous managers. I want to come back for longer!!"
Villa with private pool overlooking San Gimignano. Exclusive use of the property
VILLA TORRI - Villa Torri
Fridge, oven, dishwasher, toaster
VILLA TORRI - Villa Torri
9.4 out of 10, Exceptional, (23)
"We liked landscapes all around this area House is fully equipped and spacious Host is very kind"
VILLA TORRI - Villa Torri
Villa Paneretta - 15 nights rental: 5% discount
Interior
Villa Paneretta - 15 nights rental: 5% discount
10.0 out of 10, Exceptional, (15)
"Everything was as advertised. Spotless, lovely and incredible vistas in every direction! We will be back!!"
Villa Paneretta - 15 nights rental: 5% discount
Idyllic Countryside Retreat with Rustic Elegance
Fridge, microwave, oven, stovetop
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
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
Villa L'Elsa - Villa L' Elsa
Pool
Villa L'Elsa - Villa L' Elsa
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 L'Elsa - Villa L' Elsa
Villa Zambra by MMega
Fridge, microwave, oven, stovetop
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
Villa Vianci RBO, your home away in Tuscany
Fridge, microwave, oven, stovetop
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
Exclusive Farmhouse Pool & View of San Gimignano
Outdoor pool
Exclusive Farmhouse Pool & View of San Gimignano
10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
La Badia 2
Seasonal outdoor pool
La Badia 2
10.0 out of 10, Exceptional, (1)
"Our flight was diverted to another airport, so we were 6 hours later than expected, but able to communicate and get a quick response throughout. It's quite a small place, but there are only two of us, and we had everything we needed. The road in could be quite bumpy or extremely bumpy depending on which way, but we were able to do it in our economy car. The property host was there to meet us in the dark in a downpour, and made us feel welcome- even with a strong language barrier. Pros: view...
La Badia 2
Tignano, Barberino Val d'Elsa, Florence and Chianti
Pool
Tignano, Barberino Val d'Elsa, Florence and Chianti
10.0 out of 10, Exceptional, (1)
"Belle expérience Toscane"
Tignano, Barberino Val d'Elsa, Florence and Chianti
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
Outdoor pool, pool umbrellas, pool loungers
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
Property grounds
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
VILLA TORRI - Villa Torri
Fridge, oven, dishwasher, toaster
VILLA TORRI - Villa Torri
9.4 out of 10, Exceptional, (23)
"We liked landscapes all around this area House is fully equipped and spacious Host is very kind"
VILLA TORRI - Villa Torri
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.

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 68 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.