Holiday rentals in Poggibonsi

Holiday home in San Gimignano

4.97 out of 5 average rating, 118 reviews

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. in Experience your experience in San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with an independent entrance, first floor and breathtaking views of the Tuscan hills. Private parking space available upon request. Entrance, living room, 2 double bedrooms, kitchen, and large bathroom. city tax to add to the price, €2.5 per person per night.

Holiday home in Poggibonsi

4.95 out of 5 average rating, 173 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

4.99 out of 5 average rating, 178 reviews

Home in Gambassi Terme

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Flat in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Superhost

4.75 out of 5 average rating, 136 reviews

"In the heart of Poggibonsi"

Our small apartment is in its own historic center of the city. In a beautiful square with restaurants of typical Tuscan cuisine. Just a short walk from the bus and train station, just a 5-minute walk away. Immediately close to a small shopping center. 10 meters away is an hourly disco parking and another free parking at the station. Great location to practically and quickly reach the main attractions, San Gimignano, Siena, Florence, Colle di Val d 'Elsa

4.98 out of 5 average rating, 228 reviews

Apartment in Poggibonsi

Amaryllis House

Delightful two-room apartment located on the first floor in a central area. It consists of a living area with a sofa, kitchen, and laptop; a bedroom with a very comfortable double bed; a bathroom with a spacious and comfortable shower. Suitable for up to 2 people. Has a large terrace. It is a 10-minute walk to the station. Free parking in front of the house or at most within 200 m. Wi-Fi access available. You can walk to Siena Eye Laser in a few minutes.

Superhost

4.69 out of 5 average rating, 222 reviews

Apartment in Poggibonsi direction San Gimignano

Apartment on the first floor in the center, in an old building. , Double bed and Spacious double sofa bed (190x160) , Free parking starting from 100 m , Discount (Coop 250 meters, Lidl 750 meters, Penny 1.9 km) , easily reachable from the station (train-bus). Nearby locations: , San Gimignano (11 km by bus 15 minutes) , Siena (30 km by bus / train 30 minutes) , Volterra (35 km) , Florence (44 km by bus / train 50 minutes)

Superhost

Home in Poggibonsi

4.89 out of 5 average rating, 254 reviews

Tuscan Counrtry Detached House. Wi-Fi Free

Update: Air conditioning starting June 1st, 2025. Enjoy the summer with a cool breeze! Do you want to spend your holiday in a typical Tuscan barn? This is your place! Charming renovated barn for families / groups. Located in the heart of the Tuscan countryside at 2km from Poggibonsi. Ideal for a relaxing holiday and in a great location for visiting San Gimignano (13km), Siena (25km), Florence (35km).

4.92 out of 5 average rating, 107 reviews

Cozy apartment in the central area

VERY COMFORTABLE APARTMENT consisting of two bedrooms, bathroom and living room-kitchen with bright view on large terrace, located near the Siena Eye Laser clinic, downtown and main transport services, in fact it is about 600 meters from the train station and about 50 meters from the bus stop. Free parking is available for those traveling by car. Smoking is not allowed inside the apartment.

4.89 out of 5 average rating, 198 reviews

Farm stay in Simignano

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

4.94 out of 5 average rating, 131 reviews

Hut in Poggibonsi

Lovely barn with pool between Siena and Florence

An Independent characteristic House inside the garden of our Property. Free WiFi, Aria Condizionata, furnished veranda and Private Parking. Big Garden and equipped Pool to share only with me and my family! Siena & Florence both at Short Distance. Nearest town 5 KM away

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Popular amenities for Poggibonsi holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Poggibonsi

4.95 out of 5 average rating, 62 reviews

Il Casale di Villore, Poggibonsi, Siena, Tuscany, Morellino Apt.

OllieRating, 5 stars1 week ago

We had a wonderful few days here while touring Italy. The pool is fantastic as well as the additional facilities such as boules and table tennis. There is plenty of outdoor seating to enjoy the sunset on an evening. We would love to come back here again and would highly recommend.

4.94 out of 5 average rating, 64 reviews

Casa Sornano - apartment with a view over Chianti

SabrinaRating, 5 stars3 weeks ago

Communication with Gael was extremely easy. Although he was out of town, co-hosts Angelo and Alessandro were super friendly and attentive. We really felt at home. We would return a million times, for sure!!!

4.81 out of 5 average rating, 52 reviews

From "Jack and Adriana."

VincenzoRating, 5 stars2 weeks ago

Everything is perfect!

Apartment in Figline Valdarno

4.87 out of 5 average rating, 54 reviews

Agriturismo Casavecchia, l'Olivo

AnthonyRating, 5 stars4 weeks ago

We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.

4.97 out of 5 average rating, 34 reviews

Apartment in Tuscany with giant oak tree

AngelRating, 5 stars4 days ago

Rudi and Lydie were excellent hosts. Always kind and attentive to any needs we had. They explained the whole Airbnb to us in detail. He was always on the lookout for our arrival and the communication was excellent, at all times we felt safe and comfortable, his house and garden are very nice, we definitely recommend them!

4.91 out of 5 average rating, 44 reviews

Apartment in Poggibonsi

MD Apartment

MartinRating, 5 stars2 weeks ago

Serena is a kind, warm and attentive host. The apartment is well furnished, very clean and maintained. It offers its own parking space and is easily accessible. We felt very comfortable on site and can recommend the accommodation in every way.

5 out of 5 average rating, 16 reviews

Home in Poggibonsi

Relax in Chianti countryside

NealRating, 5 stars1 month ago

What a special place in the Tuscan hills! Beautiful house, quiet setting, yet just a short drive to many of the highlights of Tuscany. Roberto and his wife were wonderful hosts, very welcoming, and more than helpful with our non existent Italian! Really the perfect retreat! We will hope to return next time we visit the region. Grazie Mille, Roberto!