
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
Alles super. Wir haben uns sehr wohl gefühlt und hatten tolle Tage in der Toskana. Danke :)

Deal 2019 Tuscany Villa le Capanne with pool
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.

Holiday House "Le Stagioni di Bacco"
Wir hatten wundere 12 Tage in Monsummano. Das Haus liegt optimal um die Toscana zu erkunden. Die Lage ist eifach top! Zu Fuss erreicht man gute Restaurants, Eisdielen und Cafés. Wir können die Unterkunft wärmstens weiter empfehlen und Kommunikation mit Daniele war spitzenmässig!! Vielen Dank für den tollen Aufenthalt! 👌😀👍

Villa a Montepulciano con Piscina
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!

Charming estate with views
Bernardino und seine Frau Luciana haben sich bestens um uns gekümmert. Eine grosse Unterkunft, top Service, feines Essen und sehr freundlich. Absolut zu empfehlen! 10/10

Il Vichiaccio Villa con jacuzzi nel Chianti
We spent a week at Il Vichiaccio and I already miss the house. The house was perfect for a family of 5 adults. We felt immediately at home, had all what we needed. The location and views are awsom, even more beautiful than in the pictures. Plenty of great wineries and restaurants in the ares. Beatrice is a great host, answered every question we had, gave us recommendations and even helped us when our daughter didn't feel well. We strongly recommend!

Casa del Sole
Nous avons passé un superbe séjour chez Carlo et Elena. Le jardin clôturé et la piscine étaient de vrais plus. Sans compter toutes les petites attentions que Carlo a pu avoir pour nous, et même un cadeau pour notre petit chiot. Le logement est paisible entouré de montagnes avec une belle vue. Nous recommandons cette maison et son hôte car tout était parfait!

Casa Rustica, Cembroni 55022 Jacuzzi + 2 bathrooms
Siamo stati accolti dalla gentilissima signora Adolfina che ci ha dato tutte le informazioni sulla casa e sui dintorni. La casa è spaziosa, pulita, accogliente e completa di tutto. Il giardino è ben tenuto e abbiamo potuto godercelo sia noi che il nostro cane! Bellissima esperienza, da ripetere. Host consigliatissimo
Family- and pet-friendly home rentals

La Maison di Monica & Simona
Viešnagė labai patiko: būstas erdvus ir jaukus (dar gražesnis, nei nuotraukose :)), buvo viskas, ko reikia: patalynė, rankšluosčiai, viskuo aprūpinta virtuvė. Šeimininkai draugiški ir, nors nedaug kalba angliškai, bet viską paaiškina :)... Miestelis irgi žavus - kupinas istorinio dvelksmo. Visai netoli (nuo būsto gal 5 min. pėsčiomis) yra nedidelė terminė versmė - gana karšta, tad tik vienas iš mūsų maudėsi, bet kojas pamirkėme visi ;)... Miestelio bare vaišinomės vynu - buvo labai malonu pabendrauti su vietiniais gyventojais. Žodžiu, šilčiausi atsiliepimai - ačiū už viską!

Back Home - Apartment in Pienza
Valeria sempre gentile e disponibile. Arrivando con le biciclette è stata super flessibile nell'orario del check in e senza nessun problema ci ha fatto sistemare le bici in casa. Appartamento pulito e confortevole e appena fuori le mura di Pienza quindi estraneo al trambusto turistico. Lo consiglio

A due passi dal centro e lontano dal caos
Le logement de Stefania est idéal pour passer quelques jours sur Florence. Il y a tout le nécessaire et le centre reste accessible à pied ou en bus. Le frigo est un peu bruyant la nuit et cela a pu nous gêner de temps en temps.

APPARTAMENTI 3 persone+ 4 persone
Claudia ist eine tolle Gastgeberin, immer sehr hilfsbereit und super nett. Wir haben uns sehr wohl gefühlt. Die Appartements haben alles was man braucht, das Pool ist super - sehr sauber und mit einem wunderbaren Blick. Die lage ist auch top - in etwa 15 Minuten ist man in der Volterra und bis zu San Gimignano braucht man nur eine halbe Stunde. Wir kommen sehr gerne wieder und bedanken uns für das leckere Öl und den schönen Urlaub!

loft nel cuore del chianti toscano
Très bon séjour passé chez Giulia. Maison agréable et spacieuse. Bon emplacement pour découvrir le Chianti et ses chemins blancs.

Casa in Toscana con piscina
Wir haben eine wunderbare Woche in Cristinas Haus in Fabbiano verbracht und dort unsere Auszeit vom Alltag sehr genossen. Das Haus ist wunderschön in den kleinen, ruhigen, sehr romantischen Ort eingebunden. Man geniest vom Garten aus einen wunderbaren Blick in das Tal und die Berge und kann vom Haus aus auch gleich eine schöne Wanderung aus unternehmen. Cristinas Empfang war sehr herzlich und gab uns das Gefühl, uns in ihrem Haus wirklich willkommen zu fühlen. Wir konnten sie jederzeit fragen, wenn wir Rat benötigten. Der Garten ist traumhaft. Leider war es für den Pool schon zu kalt. Dafür haben wir den Kamin sehr genossen. Trotz des durchwachsenen Wetters haben wir viel unternommen denn das Haus liegt zentral zwischen Meer, den Bergen und einiger sehr schöner Städte (z.B. Viareggio, Lucca, Pisa, Bargo). Da der Garten komplett eingezäunt ist, konnte sich auch unser Hund die ganze Zeit frei bewegen. Für kleine Familien, die Ruhe und Abgeschiedenheit lieben, ist das Haus ideal

Romantic cosy flat - Toscana Italy
Vi nød virkelig opholdet i Normas hyggelige bolig. Ægte Toscana stemning med den smukkeste udsigt. Tak til Norma og familie for deres varme velkomst og hjælp undervejs. Vi vil varmt anbefale stedet til vores familie og venner

La Manonera Farmhouse "La Casa Rosa for families"
Le seul chose que je pourrais dire de négatif c’est le manque d’éclairage pour la cuisine et salle à manger . Pour le reste tout est parfait si on aime le décor de la campagne:-)
Family-friendly home rentals with a pool

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.

Private Villa with swimming pool in Tuscany
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!

12/14 pers,WiFi,Sw-pool,catering
Bellissimo agriturismo e host molto competente e disponibile. Decisamente consigliato

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.

Podere Villanuova 2
Nous avons énormément apprécié notre séjour à Podere Villanuova. Le cadre est exceptionnel, le logement confortable et meublé avec goût. Sa localisation permet d'accéder facilement avec une voiture au tramway de Florence et est bien situé pour visiter toute la région. Maurizio a été un hôte très attentionné et de bon conseil et la communication avec Giuliana très agréable. Nous recommandons.
Quick stats about vacation rentals that are family-friendly in San Gimignano
Total rentals
490 properties
Nightly prices starting at
$14 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
Destinations to explore
- Rentals with outdoor seating San Gimignano
- Kid-friendly rentals San Gimignano
- Smoking-friendly rentals San Gimignano
- Rentals with an EV charger San Gimignano
- Rentals with a patio San Gimignano
- Rentals with pools San Gimignano
- Cottage rentals San Gimignano
- Vacation home rentals San Gimignano
- Rentals with breakfast San Gimignano
- Rentals with a firepit San Gimignano
- Rentals with a fireplace San Gimignano
- Pet-friendly rentals San Gimignano
- Villa rentals San Gimignano
- Fitness-friendly rentals San Gimignano
- Farmstay rentals San Gimignano
- Rentals with a hot tub San Gimignano
- House rentals San Gimignano
- Luxury rentals San Gimignano
- Bed and breakfasts San Gimignano
- Condo rentals San Gimignano
- Hotel rentals San Gimignano
- Apartment rentals San Gimignano
- Rentals with a washer and dryer 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)
- Gulf of Baratti
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Spiaggia Libera
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Spiaggia Verruca
- Parco delle Cascine
- Mercato Centrale
- Piazza della Repubblica
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- The Boboli Gardens
- Pinocchio Park
- Cavallino Matto
- Santa Maria della Scala
- Things to do San Gimignano
- Food and drink San Gimignano
- Things to do Province of Siena
- Sightseeing Province of Siena
- Tours Province of Siena
- Art and culture Province of Siena
- Food and drink Province of Siena
- Nature and outdoors Province of Siena
- Things to do Tuscany
- Tours Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Things to do Italy
- Entertainment Italy
- Sightseeing Italy
- Sports activities Italy
- Wellness Italy
- Art and culture Italy
- Tours Italy
- Nature and outdoors Italy
- Food and drink Italy