
Family-friendly vacation rentals in Poggibonsi
Find and book unique family-friendly homes on Airbnb
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$12,550 GYD per night before taxes and fees

Verified guest reviews
Over 1,740 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!
Top-rated family-friendly rentals in Poggibonsi
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 143 reviews
Casa al Gianni - Hut
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!
4.93 out of 5 average rating, 294 reviews
Gallery Apartment near Chianti
Comfortable and bright apartment in the center of Poggibonsi, 150 meters from the Siena Eye Laser Clinic and all the necessary amenities. Ample public parking adjacent to the building. Conveniently located for reaching the cities of art, such as Florence, Siena, San Gimignano, Volterra, Pisa and the beautiful villages of Chianti. Gallery Apartment is equipped with all amenities and will welcome you as if you were at home. You can sit at the tables on the 2 terraces and drink a good Chianti or coffee in the morning.
4.95 out of 5 average rating, 154 reviews
From "Jack and Adriana."
Relax with the whole family in this quiet accommodation. Spacious apartment in Poggibonsi, furnished in Florentine style and with attention to the smallest details. Equipped with two reserved parking spaces, one of which is covered. 18 minutes from the Siena Eye Laser Clinic. In 15 minutes on foot you can reach the train station and the shopping mall. A 5-minute walk to the tobacco shop, bar, bakery, public pool and bike/pedestrian path. Perfect for the cities of Siena, Florence, San Gimignano and Volterra.
4.83 out of 5 average rating, 125 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.
5.0 out of 5 average rating, 352 reviews
Sangi Chianti Vacations
Sangi Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, near San Gimignano. 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 5 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.
4.91 out of 5 average rating, 113 reviews
Laura Chianti Holidays
Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment is halfway between Florence and Siena, and 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, 342 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
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.
4.98 out of 5 average rating, 290 reviews
Poggio Massiccioli
Cozy apartment for 4 people furnished in Tuscan style and with exposed beams immersed in the rolling hills of the Tuscan countryside. Guests have access to a furnished garden, free Wi-Fi, a shared swimming pool, a wood-burning oven, a 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.
4.92 out of 5 average rating, 389 reviews
Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
4.96 out of 5 average rating, 209 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.
4.91 out of 5 average rating, 162 reviewsPopular amenities for Poggibonsi family-friendly rentals
Family-friendly home rentals with a hot tub

SuiteLouise.pool, Hot Tub,homeGym & private Garden
4.91 out of 5 average rating, 128 reviews
Villa di Geggiano - Guesthouse
4.99 out of 5 average rating, 155 reviews
La Casetta
4.93 out of 5 average rating, 197 reviews
CasaDiManuela:TotallyPrivateChiantiVilla withTub
4.97 out of 5 average rating, 106 reviews
Nada Home
4.87 out of 5 average rating, 217 reviews
Farmhouse in Chianti with Swimming Pool
4.99 out of 5 average rating, 516 reviews
Agriturismo La Villa - L'Olivo, Pool & Hot Tub
4.98 out of 5 average rating, 241 reviews
Green Dome @ The Land Before Time Retreats
4.95 out of 5 average rating, 189 reviewsFamily- and pet-friendly home rentals

Case nell'aia Arco, apartment in Chianti and pool
4.98 out of 5 average rating, 129 reviews
Borgo Ripostena – n. 9 Frantoio
4.94 out of 5 average rating, 118 reviews
Casa Luce Modern Urban Chic Apartment in Tuscany
4.87 out of 5 average rating, 199 reviews
Villa dei 2 Ulivi (Abbadia Isola)
4.97 out of 5 average rating, 174 reviews
Suite in Castello di Valle
4.88 out of 5 average rating, 129 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
4.92 out of 5 average rating, 359 reviews
Small renovated barn
4.94 out of 5 average rating, 301 reviews
Florence Sunset Hills • Giogoli
4.88 out of 5 average rating, 342 reviewsFamily-friendly home rentals with a pool

Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Cercis - La Palmierina
4.96 out of 5 average rating, 147 reviews
Montegonfoli 5 apartment in farmhouse, 4+2 guests
4.84 out of 5 average rating, 266 reviews
Linearis apt B (4+2) Toscana
4.89 out of 5 average rating, 160 reviews
Il Castello di Ferrano - Castle in Tuscany
4.99 out of 5 average rating, 227 reviews
Charming Farmhouse Suite
4.99 out of 5 average rating, 135 reviews
Tenuta la Cipresseta | Casa Cipresso
4.98 out of 5 average rating, 41 reviewsWhen is the best time to visit Poggibonsi?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,172 GYD | G$20,917 GYD | G$21,545 GYD | G$24,055 GYD | G$23,218 GYD | G$22,591 GYD | G$26,356 GYD | G$26,565 GYD | G$27,611 GYD | G$26,774 GYD | G$20,708 GYD | G$21,336 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 |
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Gulf of Baratti
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





