
Family-friendly vacation rentals in Poggibonsi
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Poggibonsi
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Podere Vergianoni immerso nelChianti con piscina
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.

"In the heart of Poggibonsi"
Our small apartment is located in the historic center of the city. In a beautiful square with restaurants serving typical Tuscan cuisine. Within walking distance of the bus and train station, just a 5-minute walk away. Immediately next to a small shopping mall. 10 meters away there is a parking lot with a parking disc system and another free parking lot at the station. Excellent location to quickly and conveniently reach the major attractions, San Gimignano, Siena, Florence, Colle di Val d'Elsa

Gallery Apartment near Chianti
Confortevole e luminoso appartamento in centro di Poggibonsi a 150 mt dalla Clinica Siena Eye Laser e da tutti i servizi necessari. Ampio Parcheggio pubblico adiacente al palazzo. Posizione strategica per raggiungere le città d'arte come Firenze, Siena, San Gimignano, Volterra, Pisa ed i bellissimi borghi del Chianti. Gallery Apartment è dotato di tutti i confort e saprà accogliervi come a casa vostra. Potrete sedervi ai tavolini nelle 2 terrazze e bere un buon chianti o un caffè al mattino.

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.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Casa Amaryllis
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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Poggio Massiccioli
Cozy apartment for 4 people furnished in Tuscan style and with exposed beams nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.
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).

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.

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,

Casa al Gianni - Hut
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!
Popular amenities for Poggibonsi family-friendly rentals
Family-friendly home rentals with a hot tub

A Big Dream in a Little Tower.

"Red Rose" apartment with view of Siena.

Il Fienile, Cottage in the country with Jacuzzi

Torretta Apartment

San Giovanni in Poggio, Villa Meriggio 95 sqm

Romantic Siena summer spa Francigena road

La Villa farm stay - L'Olivo, Pool & Hot Tub

Charming estate with views. A/C in the bedrooms
Family- and pet-friendly home rentals

Bright apartment with terrace and towers view

Antico Borgo Ripostena – n. 9 Oil Mill

Fienile Santa Teresa

Casa Al Poggio & Chianti view

House for the Coast

Lovely barn with pool between Siena and Florence

Monteriggioni Castello, holiday house in Tuscany

In the center of Tuscany
Family-friendly home rentals with a pool

Tenuta Chiudendone in Tuscany

StageROOM03 - Idyllic Chianti cottage near Siena

Stone House with Exclusive Pool Codilungo in Chianti

Explore Chianti from a Charming Stone House

apartment with great views

Countryside Dream farm in Tuscany

Agriturismo I Gelsi

Podere Villetta La Colombaia
When is the best time to visit Poggibonsi?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$18,202 GYD | G$16,738 GYD | G$20,922 GYD | G$23,433 GYD | G$23,433 GYD | G$26,153 GYD | G$26,362 GYD | G$26,571 GYD | G$27,617 GYD | G$26,780 GYD | G$20,713 GYD | G$21,341 GYD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Quick stats about vacation rentals that are family-friendly in Poggibonsi

Total vacation rentals
Explore 40 vacation rentals in Poggibonsi

Nightly prices starting at
Poggibonsi vacation rentals start at G$12,553 GYD per night before taxes and fees

Verified guest reviews
Over 1,500 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Poggibonsi vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Poggibonsi rentals

4.8 Average rating
Poggibonsi stays are highly rated by guests—averaging 4.8 out of 5!
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- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Mercato Centrale
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Marina di Cecina
- Porta Elisa
- Del Chianti
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Spiagge Bianche
- Eremo Di Camaldoli
- Cala Violina
- Piazza del Duomo (Pisa)
- Piazza della Signoria
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Piazza della Repubblica
- Parco delle Cascine




