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Family-friendly vacation 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 in San Casciano in Val di pesa
4.95 out of 5 average rating, 136 reviews

Il Fienile, Cottage in the country with Jacuzzi

KatharineRating, 5 stars2 weeks ago
We absolutely loved our stay at Massimo's home. It is a peaceful sanctuary with stunning views of the surrounding vineyards. There is plenty of room for adults to sleep comfortably. Massimo and Beatrice were helpful with providing recommendations in the area for wine tours and restaurants and friendly to us during the stay. Highly recommend it for a homey getaway in Chianti!
Guest favourite
Home in Monsummano Terme
4.98 out of 5 average rating, 106 reviews

Holiday House "The Seasons of Bacchus"

KanchayaRating, 5 stars5 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 in Reggello
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!
Guest favourite
Home in Gaiole In Chianti
4.86 out of 5 average rating, 253 reviews

Charming estate with views

GillianRating, 5 stars1 week ago
What a fantastic find!! Bernadino and Edoardo were superb hosts at the beautiful house overlooking the vineyards. It had all the amenities you could wish for and was spotlessly clean. Edoardo cooked for us one evening and it was so delicious and reasonably priced. I would gladly have had her cook for us every evening!! A perfect stay, couldn’t have asked for more 😊
Top guest favourite
Apartment in Centro Storico
4.94 out of 5 average rating, 295 reviews

M&G Apartment your home away from home

TimothyRating, 5 stars3 weeks ago
Max was great! Very responsive and friendly. The apartment itself was very nice—quite clean.
Guest favourite
Villa in San Casciano in Val di Pesa
4.94 out of 5 average rating, 165 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

GretaRating, 5 stars5 days ago
Lovely place I stayed with my friends. We all had a good time because the house is equipped with all the comforts both in the kitchen and in the rooms. A magical place
Top guest favourite
Cottage in Geggiano
4.99 out of 5 average rating, 128 reviews

Villa di Geggiano – Guesthouse

PeggyRating, 5 stars1 week ago
A peaceful and relaxing stay in the beautiful countryside. The unit is private & gorgeously renovated & bedroom overlooks vineyard. The hosts- Andrea & his brother were very welcoming, helpful and friendly, with lots of local suggestions. The main villa tour is also amazing. All in all a wonderful stay! Thank you!
Guest favourite
Farm stay in Figline Incisa Valdarno
4.94 out of 5 average rating, 351 reviews

Romantic stay at a bio-agritourism in Florence

TravisRating, 5 stars3 weeks ago
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

Superhost
Apartment in Sasso Pisano
4.78 out of 5 average rating, 187 reviews

La Maison di Monica & Simona

MaximeRating, 5 stars3 months ago
Monica is very welcoming. The value for money is very good. Be careful if you have small children because there are slightly steep stairs to access the accommodation.
Top guest favourite
Apartment in Pienza
4.9 out of 5 average rating, 162 reviews

Back Home - Apartment in Pienza

MorganRating, 5 stars3 weeks ago
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!
Guest favourite
Guest suite in Centro Storico
4.95 out of 5 average rating, 167 reviews

Within walking distance of the center and away from the chaos

ValentinRating, 5 stars1 month ago
Matrace is of memory foam. I slept very well but just something you should know if you don‘t like this type of matrace. Extra blankets were there and overall super comfortable bed. Wifi speed was fine, not as fast as I would have liked. Host was really nice. We would definitely come back here! Use the app „easypark“ for nearby affordable parking on a „pay as you go“ basis. Shop im the nearby esselunga supermarket.
Superhost
Home in Staggia
4.87 out of 5 average rating, 39 reviews

Holiday in the Chianti Senese

JosefinRating, 5 stars8 months ago
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.
Superhost
Apartment in Volterra
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 it only takes half an hour to get to San Gimignano. We will be happy to come back and thank you for the delicious oil and the beautiful vacation!
Superhost
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft in the heart of Tuscan Chianti

CharlotteRating, 5 stars5 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.
Top guest favourite
Villa in San Leolino
5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

VeraRating, 5 stars5 months ago
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!
Guest favourite
Farm stay in Sovicille
4.9 out of 5 average rating, 164 reviews

House at Gianni - Leccio

AndrewRating, 5 stars1 week ago
Had a very great time staying here. Cristina was very friendly and communicative with us on how to get in and happy to answer any questions or help us out with our stay if needed. We found the place we stayed in to be very nice, had a really fun farm feel that we enjoyed. The grounds were well kept and it was nice to be able to walk around a little bit and explore the area and see all of the animals.

Family-friendly home rentals with a pool

Top guest favourite
Villa in Siena
4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

MarkRating, 5 stars6 months ago
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!
Guest favourite
Villa in Baco
4.86 out of 5 average rating, 83 reviews

Tuscan Villa

DeeRating, 5 stars6 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 in Ortignano Raggiolo
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
Apartment in Montespertoli
4.89 out of 5 average rating, 9 reviews

12/14 people, WiFi, SW pool, catering

MartinaRating, 5 stars24 months ago
The place is magnificent and very well kept, clean and super cozy. It's a little out of the way but we chose it just for the secluded location and surrounded by nature; in any case with a halfhour by car you can get to several wonderful places. Nicola was very kind and helpful. I highly recommend a stay here, it's refreshing!!
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 stars5 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
Apartment in La Felce
4.98 out of 5 average rating, 107 reviews

La Felce Country House

GarrettRating, 5 stars6 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
Apartment in Capannori
4.91 out of 5 average rating, 34 reviews

Casa Colle

SallyRating, 5 stars6 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.
Guest favourite
Farm stay in Gaiole In Chianti
4.97 out of 5 average rating, 100 reviews

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2

KimberleyRating, 5 stars6 months ago
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

    $56 CAD 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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