Holiday houses in Poggibonsi

Farm stay in San Gimignano

4.89 out of 5 average rating, 208 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

Holiday home in Poggibonsi

4.95 out of 5 average rating, 172 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.

Condo in Colle di Val d'Elsa

4.98 out of 5 average rating, 180 reviews

DorminColle - Tuscan-style apartment

Appartamento luminoso e spazioso, composto da confortevole camera matrimoniale con tv, condizionatore portatile, con al suo interno bagno completo di doccia e servizi igienici. Terzo posto letto situato in caratteristica area soppalcata con travi in legno dotato di letto. Ampia cucina dotata di lavastoviglie, macchina del caffè, microonde, erogatore acqua filtrata, Salone con tv e divano, sala da pranzo con vista sul Borgo Antico. Parcheggio gratuito a 150 mt visibile dell’appartamento.

4.99 out of 5 average rating, 276 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

4.98 out of 5 average rating, 227 reviews

Condo 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

4.75 out of 5 average rating, 134 reviews

"In the heart of Poggibonsi"

Our small apartment is in its own historic center of the city. In a nice 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

4.93 out of 5 average rating, 118 reviews

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

4.87 out of 5 average rating, 181 reviews

Casa Luce Modern Urban Chic Apartment in Tuscany

Enjoy Tuscany in our cozy cute apartment, very conveniently located between Florence and Siena and ideal if you want to explore the countryside. The neighborhood is quiet with free parking outside the building. There is a market store, bar, butcher, beauty salon, and cafes all nearby walking distance. Also you can come to visit our organic farm and get fresh veggies, fruit and eggs you can cook at home. Smoking is allowed only on the balcony.

4.91 out of 5 average rating, 323 reviews

Apartment in Gavignano

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams immersed in the rolling hills of the Tuscan countryside. Equipped garden, free wi-fi, equipped shared swimming pool, wood-burning oven and barbecue,washing machine are available for guests. The apartment was obtained from a charming stone farmhouse of 1800 recently renovated according to the Tuscan tradition and divided into three comfortable apartments

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, 106 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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Poggibonsi holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Poggibonsi

4.93 out of 5 average rating, 45 reviews

Villa in Poggibonsi

Villa with pool in Chianti Area

RickRating, 5 stars1 week ago

Our stay at Mariella's beautiful home was a highlight of our five week trip throughout Italy. Peacefully situated between Florence and Siena, this villa offers a welcoming respite from the hustle and bustle of the cities. It was also super convenient to the vineyards throughout Chianti. Waking up every morning to the sunrise views over the valley and enjoying a glass of wine in the evening were the perfect beginning and ending to each day. The pool was even larger than we imagined and provided days of entertainment sprinkled in during a week of sightseeing and wine tasting. I cannot recommend this home, location, or host enough. You will NOT be disappointed!

4.95 out of 5 average rating, 61 reviews

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

JohnRating, 5 stars2 months ago

We spend here 4 nights with our dog and felt right at home. I love nature and I love to cook and the kitchen being small has everything and a window on the Tuscan landscape, Considering we were not lucky with the weather Antonio gave us a few great tips what to do and we had an amazing time! Also special shoutout to sweet Tilda ❤️ we miss her already John Olya Floyd

Guest suite in Poggibonsi

4.78 out of 5 average rating, 116 reviews

Santa Lucia - Siena

KiraRating, 5 stars1 month ago

We had a really nice time. The location is great for exploring Tuscany, the way to the accommodation is a bit adventurous, but you get used to it. The accommodation is very cozy and has its own charm.

4.94 out of 5 average rating, 87 reviews

Condo in Poggibonsi

Gallery Apartment near Chianti

NinaRating, 5 stars2 weeks ago

The apartment is very beautiful. We found everithing we needed. The owners left us fresh water and milk in the fridge, so we colud make us a coffee. There were also some packed sweets left for us. We stayed only one night because we were exploring different places in Tuscany. Giuseppe and Laura were very helpful with advices and very responsive, so we had no problems with check-in. The street is a bit busy, but no problem finding a free parking place near by. We had a great short stay there.

4.98 out of 5 average rating, 52 reviews

App.Falegnameria

AlfredoRating, 5 stars1 month ago

Beautiful stay and lovely hosts

4.97 out of 5 average rating, 33 reviews

Apartment in Tuscany with giant oak tree

MirandaRating, 5 stars2 weeks ago

Rudi and Lydia are great people. Extremely hospitable, helpful and with a broad interest. The yard is beautiful. You reach the house via a strada bianca. The cottage is well and attractively decorated. You have a private garden, but apart from that, you can look and use it anywhere. We had wonderful days and will definitely come back. We have friends with us

Barn in Castellina in Chianti

5 out of 5 average rating, 26 reviews

Cipressini 2 - pool and amazing views

BrandonRating, 5 stars2 weeks ago

We cannot say enough about how fantastic our stay was. Maybe the most gorgeous property we’ve ever seen - even better than the pictures! Pia was incredibly helpful, sent us a whole printout of recommendations for different restaurants, wineries, and things to do. She is incredibly kind, responsive, and proactive - she thought of everything you may need during your stay and gave us a tour of our home. Waking up in the Tuscan countryside and watching the sun rise over the vineyards was relaxing and beautiful. The sunsets were breathtaking to see over the rolling hills in Chianti. Castellina was a cute little town with fantastic places to eat and panoramic views of the valley. And on top of all that, we made a new friend in the Public Relations Manager, Teo - you can be sure you’ll be greeted with a wagging tail and a happy little smile. Couldn’t recommend this place highly enough!