
Family-friendly vacation rentals in San Gimignano
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in San Gimignano
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for San Gimignano family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi
This was our second time at Il Vichiaccio and I hope it's not the last. In fact, this Airbnb is the entire reason we had Tuscany on our trip itinerary. Beatrice and Massimo are the most wonderful hosts in the world. Besides simply being great people to chat with, they are hospitable in providing some of their homemade wine and eggs. There's nothing more special than relaxing in the hot tub with the vineyard views and walking up the hill to dinner at Il Cavaliere in the castle. Our only complaint is that we did not see the kitty cat this time! She was our favorite host when we visited 3 years ago. Oh well, I guess we'll have to book again soon and try once more :)

Holiday House "The Seasons of Bacchus"
The house is so nice, clean and cozy. Daniele gives us many helpful tips and place to go, very nice and proactive host.We enjoy our stay very much thanks to Daniele. The place is peaceful and easy to go anywhere, Pisa, Lucca, Florence and Cinque terra. Such a lovely house , highly recommend for family trip👍🏼

CASA AL BOSCO 1
We had a very pleasant time here. Carlotta was very friendly from the start, and even recommended local grocery stores. This place is a hidden gem! You are surrounded by beautiful trees & nature, but close enough to the town where you can easily catch the train to Florence. We absolutely loved it!

Charming estate with views
We had such a lovely stay at Bernardino’s villa! He greeted us when we arrived and made sure we had everything we needed. The home is very charming and peaceful, and centrally located to explore Tuscany. Would definitely recommend!

M&G Apartment your home away from home
Massimiliano is a great host. Lives in the apartment next door so very easy to get inside and readily available to help. The apartment has a bit of that old school charm that we personally enjoyed. Clean apartment, clean bedding, bedrooms are good size (one bedroom with large bed, fit two adults and a baby), and the other bedroom has three single beds. The living area has a small couch in it (fits two adults max) and a small TV. The only two things I would advise on are that the elevator doesn’t work to get you to the third floor, so be ready to carry your luggage up two flights of stairs. The second, floor is screeching in the living area anytime you step on it. Didn’t bother us, but flagging for you. Finally, the location is about a 10 minute walk away from the actual city centre. Again, not a big deal for us since we are a young active family but just to make you aware. There are some amazing coffee shops along the way though so we did enjoy the stroll. Overall great stay, thanks!

The Vichiaccio Villa with Jacuzzi in Chianti
Beatrice was a wonderful host and accommodating of our needs traveling with a two year old. She was very responsive and gave amazing recommendations for places to eat and visit. The location is stunning - even more beautiful than the pictures! Every direction you look has rolling vineyards. We opted to have them cook a special birthday meal one of the nights, and it was delicious. The only small downside is there isn’t a common area to spend time in besides the kitchen (just the layout of the house). We loved it and hope to come back some day!

Villa di Geggiano – Guesthouse
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!

Romantic stay at a bio-agritourism in Florence
From the location, to the space itself, everything was perfect and an amazing place to stay the weekend. Our favorite part was the fireplace in the bedroom! we would love to come back!
Family- and pet-friendly home rentals

La Maison di Monica & Simona
Really enjoyed the stay: the place is spacious and cozy (even more beautiful than in the pictures :)), there was everything you need: bed linen, towels, everything equipped with kitchen. The hosts are friendly and although they don't speak much English, but they explain everything:)... The town is charming too - full of historical buzz. There is a small thermal spring quite close (from the property maybe 5 min walk) - quite hot so only one of us bathed, but our feet were all soaked;)... We had a wine at the townhome's bar - it was very nice to interact with the locals. Literally, the warmest feedback - thank you for everything!

Back Home - Apartment in Pienza
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

Within walking distance of the center and away from the chaos
We had a fantastic experience at Stefania's place! It's a beautiful studio which was spotlessly clean and has everything you might need. Slightly out of the centre of Florence (in a lovely area, we recommend the walk from the flat to Piazzale Michelangelo for stunning views) but you can get the 11 bus into the city. The bus isn't always reliable on weekend and evening so we often walked back to the flat, the hill looks intimidating but it's a relatively easy walk. Stefania was very responsive and had good recommendations for us. There is also a super cute cat in the building that was friendly.

Antico Borgo Ripostena – n. 5 Garage
Marina's place is one of the most beautiful places I've ever seen. The attention to details, the amenities and her communication made our stay very relaxing and enjoyable. Thanks Martina for a great stay in Tuscany.

APARTMENTS 3 people + 4 people
Claudia is a great hostess, always very helpful and super nice. We felt very comfortable. The apartments have everything you need, the pool is great - very clean and with a wonderful view. The location is also great - in about 15 minutes you are in the Volterra and up to San Gimignano you only need half an hour. We will be happy to come back and thank you for the delicious oil and the nice holiday!

loft in the heart of Tuscan Chianti
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.

Poggio del Fattore-Villa with pool, hilltop, Chianti
A truly stunning place with incredibly welcoming hosts. The villa exceeded our expectations in every way. The interior is filled with beautiful historic furniture, details, paintings, and books. The cozy fireplace in the living room added a special charm. We loved making pizza in our very own wood-fired oven, using the outdoor BBQ, and dining al fresco surrounded by breathtaking views. Every moment at Poggio del Fattore felt special, offering the perfect blend of comfort and authenticity. Highly recommended for anyone looking to experience the beauty of the Tuscan countryside in style!

House at Gianni - Leccio
Our stay on the farm enchanted us! The environment is amazing. The apartment was clean and bigger than the pictures. We were able to have farm products (meat, pasta, eggs, beers) and enjoy the facilities (ping pong, freesbee, badminton) The kids loved being able to see the pigs and donkeys up close. A fireplace to top it all off, a stay in the heart of nature that is truly exotic and relaxing. Super responsive, friendly and attentive host. 👍👍
Family-friendly home rentals with a pool

Tuscan Villa with Privacy,Pool,near towncentre
Heavenly environment, in spectacular scenery, very close to the center. House full of all comforts, elegant, perfect for a totally relaxing stay. Antonio is always ready to meet your every request, kind, friendly and hospitable. Definitely to be returned to!!

Enchanting Rose Garden Pool Villa
We booked Villa Montechiarone as part of our wedding at Montechiaro Organic Winery to house a group of 7 guests. The property sits around 500m from the winery itself, with views out over the Tuscan countryside, it's a breathtaking location and the villa itself is an incredible space. There are 2 huge indoor living areas, a well equipped kitchen, 4 spacious bedrooms and an outdoor covered terrace, as well as the garden and pool area. There is real character in the property in the way it is decorated as well as the imposing facade of the building itself. The pool area is spacious and well placed to take in the most of the view, and there is a car port with parking for at least 4 cars covered, with plenty more room if required beyond. Overall perfect for housing our guests who had a great experience and were very thankful for the help whilst checking out also!

Tuscan Villa
Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.

12/14 people, WiFi, SW pool, catering
Beautiful farm and very competent and available host. Definitely recommended

Casa di Lyndall - Entire house with exclusive pool
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!

La Felce Country House
Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!

Casa Colle
We had a very relaxing few days staying with Lucy and her family, and their dog Amber. They were really friendly and welcoming, and always ready to answer any queries we had. The pool area was lovely, and extremely peaceful. The accommodation was spacious, very clean and comfortable. The village is small with a butchers and bakers, a couple of restaurants and a bar. We did a lovely circular walk from the property through the woods to the nearby hill top village, Castel Vecchio. There’s nothing in the village but it’s very pretty and the views are great. You need a car to get to the supermarket and Lucca is a very easy 20 minute drive away. We had a super time and thank you Lucy for your generous hospitality.

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2
Paula has not only created a beautiful sanctuary that perfectly reflects Tuscan culture, but offers wine tasting and a vineyard tour on her property. The location of this gem of a place is centrally located in the Chianti region , making it a perfect home base for day trips to Assisi, Firenze and nearby small villages that offer great restaurants and quaint shops. The region is cycling friendly, as well as offering places for day hikes. Staying here for five days was one of highlights of our Italian adventure.....and we highly recommend experiencing the perfect place to stay in Tuscany and the warmth and friendliness that Paula, Ferderico and her staff offer!!
Quick stats about vacation rentals that are family-friendly in San Gimignano
Total rentals
490 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
12K reviews
Pet-friendly rentals
200 properties allow pets
Rentals with a pool
320 properties have a pool
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Destinations to explore
- Florence Vacation rentals
- Pisa Vacation rentals
- Elba Vacation rentals
- Bologna Vacation rentals
- Cinque Terre Vacation rentals
- Portofino Vacation rentals
- Riviera di Levante Vacation rentals
- Genoa Vacation rentals
- Italian Riviera Vacation rentals
- Rome Vacation rentals
- Verona Vacation rentals
- Venice Vacation rentals
- Rentals with a hot tub San Gimignano
- Rentals with outdoor seating San Gimignano
- Smoking-friendly rentals San Gimignano
- Rentals with breakfast San Gimignano
- Rentals with a fire pit San Gimignano
- Fitness-friendly rentals San Gimignano
- Apartment rentals San Gimignano
- Rentals with a washer and dryer San Gimignano
- Kid-friendly rentals San Gimignano
- Farmstay rentals San Gimignano
- Villa rentals San Gimignano
- Pet-friendly rentals San Gimignano
- Vacation home rentals San Gimignano
- Rentals with a fireplace San Gimignano
- Rentals with an EV charger San Gimignano
- Cottage rentals San Gimignano
- House rentals San Gimignano
- Bed and breakfasts San Gimignano
- Luxury rentals San Gimignano
- Rentals with a patio San Gimignano
- Rentals with pools San Gimignano
- Condo rentals San Gimignano
- Hotel rentals San Gimignano
- Family-friendly rentals Province of Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Spiaggia Libera
- CavallinoMatto
- Spiaggia Verruca
- Uffizi Gallery
- Piazzale Michelangelo
- Parco delle Cascine
- Stadio Artemio Franchi
- Mercato Centrale
- Piazza della Repubblica
- The Boboli Gardens
- Teatro Verdi
- Pitti Palace
- Basilica di Santa Croce
- Pinocchio Park
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Things to do San Gimignano
- Food and drink San Gimignano
- Things to do Province of Siena
- Food and drink Province of Siena
- Art and culture Province of Siena
- Sightseeing Province of Siena
- Nature and outdoors Province of Siena
- Sports activities Province of Siena
- Tours Province of Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Wellness Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Things to do Italy
- Sightseeing Italy
- Nature and outdoors Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Sports activities Italy
- Tours Italy
- Entertainment Italy
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes