Vacation rentals in Poggibonsi

5 out of 5 average rating, 250 reviews

Condo in Noce

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

4.99 out of 5 average rating, 188 reviews

Home in San Gimignano

Garden House

"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

Vacation home in Poggibonsi

4.95 out of 5 average rating, 171 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, 275 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, 225 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.

4.74 out of 5 average rating, 133 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.

4.69 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)

4.89 out of 5 average rating, 253 reviews

Home in Poggibonsi

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).

4.91 out of 5 average rating, 103 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.

5 out of 5 average rating, 116 reviews

Villa Mocarello "IL LECCIO"

This romantic apartment is located on the second floor of a 19th century Leopoldinian Villa. The independent entrance can be reached walking through the lush garden surrounding the house. The Villa is located in a strategic position in the middle of Tuscany, close to Florence, Siena and San Gimignano. the bus station is about ten minutes on foot, the train station about fifteen minutes,

4.89 out of 5 average rating, 195 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!

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Popular amenities for Poggibonsi vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Poggibonsi

4.87 out of 5 average rating, 15 reviews

In the Heart of Tuscany

LowriRating, 5 stars3 weeks ago

Really lovely stay at Viola’s, hospitable and looked exactly like the pictures. Lovely staff and such a spacious and clean location- would recommend.

4.94 out of 5 average rating, 63 reviews

Casa Sornano - apartment with a view over Chianti

SarahRating, 5 stars1 month ago

We had a wonderful stay at casa Sornano. The unit was large, well stocked and clean. It was in a quiet rural location 10 minutes from Poggibonsi. The host Alessandro communicated very clearly and was very responsive to our requests. He went above and beyond to make us feel comfortable. They were also very accommodating for our baby, providing a cot and highchair. Also the recommendations they provided were all amazing- contributing to our really wonderful stay in Tuscany.

4.95 out of 5 average rating, 61 reviews

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

JohnRating, 5 stars1 month 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

Home in Barberino Tavarnelle

4.97 out of 5 average rating, 71 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars6 days ago

How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

4.82 out of 5 average rating, 49 reviews

From "Jack and Adriana."

MauroRating, 5 stars1 week ago

The lady welcomed us with extreme cordiality and kindness, offering us a bottle of wine. Positive experience

4.97 out of 5 average rating, 33 reviews

Apartment in Tuscany with giant oak tree

MirandaRating, 5 stars1 week ago

Rudi and Lydia are amazing people. Extremely welcoming, 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 piece of private garden, but apart from that, you can look everywhere and use it. We had wonderful days and will definitely be back. We have friends with us

Apartment in San Gimignano

4.98 out of 5 average rating, 41 reviews

Herons Superior Apartment - Splendid view!

JanineRating, 5 stars1 month ago

Words can’t describe how beautiful the view is from the apartment! We had a lovely week in San Gimignano with our six month old. So peaceful and everything within walking distance. Communication was great and use of the parking garage was much appreciated. Would definitely recommend!