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Family-friendly holiday rentals in San Gimignano

Find and book unique family-friendly homes on Airbnb

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Popular amenities for San Gimignano family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Cottage
4.95 out of 5 average rating, 139 reviews

Il Fienile, Cottage in the country with Jacuzzi

MilesRating, 5 stars1 week ago
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 :)
Guest favourite
Home
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Guest favourite
Home
4.98 out of 5 average rating, 107 reviews

Holiday House "The Seasons of Bacchus"

KanchayaRating, 5 stars6 months ago
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👍🏼
Guest favourite
Loft
4.89 out of 5 average rating, 131 reviews

CASA AL BOSCO 1

AlejandraRating, 5 stars6 months ago
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!
Superhost
Home
4.86 out of 5 average rating, 255 reviews

Charming estate with views

BriRating, 5 stars1 week ago
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!
Guest favourite
Villa
4.94 out of 5 average rating, 167 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

AnnabelleRating, 5 stars2 weeks ago
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!
Top guest favourite
Cottage
4.99 out of 5 average rating, 129 reviews

Villa di Geggiano – Guesthouse

LauraRating, 5 stars3 weeks ago
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!
Guest favourite
Flat
4.93 out of 5 average rating, 28 reviews

Il Fienile, pool, hot tub, sauna, quiet located

TatianaRating, 5 stars7 months ago
Everyone was very nice, the neighbors were very nice, A nice place to rest, a big thank you personally to Maria. For the address, the GPS told us that we had arrived, but we had to continue the road for about 300 m. And Borgo Isora will be on your left. The road is winding to get there, you have to be careful. Very nice place to go.

Family- and pet-friendly home rentals

Superhost
Flat
4.78 out of 5 average rating, 189 reviews

La Maison di Monica & Simona

JurgitaRating, 5 stars1 week ago
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!
Top guest favourite
Flat
4.9 out of 5 average rating, 163 reviews

Back Home - Apartment in Pienza

MorganRating, 5 stars1 month ago
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!
Guest favourite
Guest suite
4.95 out of 5 average rating, 169 reviews

Within walking distance of the center and away from the chaos

HannaRating, 5 stars1 week ago
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.
Superhost
Flat
5 out of 5 average rating, 4 reviews

APARTMENTS 3 people + 4 people

KasiaRating, 5 stars33 months ago
Claudia is a great host, 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!
Superhost
Home
4.8 out of 5 average rating, 100 reviews

loft in the heart of Tuscan Chianti

CharlotteRating, 5 stars6 months ago
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.
Guest favourite
Farm stay
4.9 out of 5 average rating, 168 reviews

House at Gianni - Leccio

Dav Et LaetRating, 5 stars3 days ago
We were delighted with our stay at the farm! The environment is amazing. The apartment was clean and bigger than the pictures. We were able to have farm products (meat, dough, 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, stay in the heart of nature really exotic and relaxing. Very responsive, friendly and attentive host 👍👍
Top guest favourite
Apartment
4.99 out of 5 average rating, 176 reviews

Pink like the sunset sky

JingmingRating, 5 stars6 days ago
Very lovely place, clean and beautiful. Lucia is very friendly and responsive for everything. Thank you
Guest favourite
Flat
4.91 out of 5 average rating, 162 reviews

Pieve di Caminino Historic Farm

SusannaRating, 5 stars2 months ago
the property is a dream.. we stayed in the Foresteria, better than the photos!!! Perfect place for those looking for tranquility while respecting and in full contact with nature. Emiliano is a wonderful host, he made us find the fireplace lit, he allowed us to bring our dogs and leave them free in his beautiful estate and he gave us many tips on activities to do in the surroundings... we can't wait to go back !!

Family-friendly home rentals with a pool

Superhost
Home
4.88 out of 5 average rating, 50 reviews

Tuscan Villa with Privacy,Pool,near towncentre

GaiaRating, 5 stars3 days ago
Paradise environment, in a spectacular setting, very close to the center. House full of all comforts, elegant, perfect for a total relaxing stay. Antonio is always ready to meet your every request, kind, friendly and hospitable. Definitely back!!
Guest favourite
Villa
4.86 out of 5 average rating, 83 reviews

Tuscan Villa

DeeRating, 5 stars7 months ago
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.
Top guest favourite
Villa
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars6 months ago
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!
Superhost
Flat
4.9 out of 5 average rating, 10 reviews

12/14 people, WiFi, SW pool, catering

AndreaRating, 5 stars2 weeks ago
Beautiful farm and very competent and available host. Definitely recommended
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars6 months ago
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!
Top guest favourite
Flat
4.98 out of 5 average rating, 107 reviews

La Felce Country House

GarrettRating, 5 stars7 months ago
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!
Guest favourite
Farm stay
4.94 out of 5 average rating, 171 reviews

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza

BradRating, 5 stars1 week ago
Sabrina and her family were very accommodating and amazing host! The whole stay was superb In every way and my whole family as well as myself noted it couldn’t have been a better experience. From the amazing home cooked breakfast, to the cleanliness of the house, and the well thought out and led cooking class/dinner we enjoyed every aspect. Sabrina was very welcoming and made you feel like family :) I would highly recommend to anyone looking for a peaceful farm style stay that wants to experience Tuscany.
Guest favourite
Flat
4.91 out of 5 average rating, 34 reviews

Casa Colle

SallyRating, 5 stars7 months ago
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.

Quick stats about holiday rentals that are family-friendly in San Gimignano

  • Total rentals

    490 properties

  • Nightly prices starting at

    £8 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

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