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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 favorite
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
Cottage in San Casciano In Val di Pesa
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 favorite
A metal staircase leads to a loft area, framed by a wall adorned with a mural of grapevines. The space features light-colored wooden flooring and is illuminated by natural light from a nearby window.
Home in Monsummano Terme
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 favorite
A spacious outdoor area is shown, featuring comfortable lounge chairs and a wooden table set for dining. The setting includes lush greenery and a stone wall, creating a peaceful atmosphere. A shaded patio area enhances the inviting outdoor space, perfect for relaxation.
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!
Superhost
A sunlit sunroom features large windows adorned with sheer curtains, allowing natural light to fill the space. A cozy white sofa is positioned next to a small wooden table with chairs, while indoor plants add a touch of greenery to the inviting atmosphere.
Home in Gaiole in Chianti
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!
Top guest favorite
A welcoming living area highlights a decorative fireplace framed by ornate mirrors, illuminated by natural light from large windows. Cozy seating includes an orange armchair and a wooden coffee table rests atop an intricately patterned rug. Wall art adds character to the space.
Apartment in Centro Storico
4.94 out of 5 average rating, 298 reviews

M&G Apartment your home away from home

YairRating, 5 stars1 week ago
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!
Guest favorite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa
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 favorite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
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 favorite
A warm bedroom features a cozy working fireplace made of stone. A spacious bed is dressed in neutral tones, complemented by soft lighting from a bedside lamp. An arched window allows natural light to enter, framed by wooden shutters.
Farm stay in Figline e Incisa Valdarno
4.93 out of 5 average rating, 352 reviews

Romantic stay at a bio-agritourism in Florence

TravisRating, 5 stars1 month 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
A panoramic view of Sasso Pisano is captured, featuring historic stone buildings nestled among lush green hills. The clock tower stands prominently, while tree-covered slopes provide a natural backdrop, highlighting the town's rustic charm and tranquil setting.
Apartment in Sasso Pisano
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 favorite
An open living space features a colorful polka-dotted sofa and a small dining table surrounded by vibrant chairs. The kitchen area is organized with shelves displaying kitchenware and appliances, with a warm wooden ceiling enhancing the cozy atmosphere.
Apartment in Pienza
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 favorite
A bright living area features a beige sofa with a pink cushion and a red coffee table, complemented by a sleek kitchenette and a minimalist bookshelf filled with various books. Natural light is captured through a nearby door, enhancing the open feel of the space.
Guest suite in Centro Storico
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.
Guest favorite
A serene bedroom features a wrought iron bed with white linens and a soft brown quilt. Natural light filters in through a partially open door, revealing an outdoor area. A small wooden table holds a vase with flowers, complementing the rustic decor.
Home in Pievescola
4.93 out of 5 average rating, 124 reviews

Antico Borgo Ripostena – n. 5 Garage

KeriRating, 5 stars6 months ago
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.
Superhost
A swimming pool is depicted with clear blue water, reflecting sunlight. A child is seen jumping into the pool, creating ripples. A second child can be observed swimming nearby, with lush green trees and rolling hills visible in the background.
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 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!
Superhost
A spacious living area features a wooden-beamed ceiling and large windows allowing for natural light. A red sofa and rustic wooden table create a comfortable setting. A stone fireplace is positioned in the corner, adding a warm element to the welcoming environment.
Home in Gaiole in Chianti
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.
Top guest favorite
The stone farmhouse features vibrant red shutters and a terracotta roof. A spacious patio area contains a wooden dining set, surrounded by lush green grass and tall cypress trees. The exterior is complemented by well-maintained stone pathways, inviting guests to explore the outdoor space.
Villa in San Leolino
5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

VeraRating, 5 stars6 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 favorite
A rustic wooden cart is positioned under the shade of large trees, with a child and an adult seated on it. A sheep grazes nearby, while the agriturismo buildings are seen in the background, surrounded by lush greenery.
Farm stay in Sovicille
4.9 out of 5 average rating, 168 reviews

House at Gianni - Leccio

Dav Et LaetRating, 5 stars2 days ago
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

Superhost
Home in Volterra
4.88 out of 5 average rating, 50 reviews

Tuscan Villa with Privacy,Pool,near towncentre

GaiaRating, 5 stars2 days ago
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!!
Top guest favorite
A clear blue pool is framed by lush greenery and terracotta paths, with several lounge chairs positioned nearby. The house sits atop a gentle hill, surrounded by tall trees and vibrant shrubs, offering a serene perspective of the Tuscan landscape.
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 favorite
A large private swimming pool features clear turquoise water, surrounded by sun loungers and umbrellas. Olive trees are visible nearby, and a traditional farmhouse stands in the background against a clear blue sky, providing an inviting outdoor space for relaxation.
Villa in Baco
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.
Superhost
Apartment in Montespertoli
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 favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
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 favorite
A serene pool area is surrounded by lush greenery, featuring a large swimming pool with colorful floats. Comfortable sun loungers are positioned nearby on the stone deck, offering a relaxing spot to soak in the sun. Soft clouds drift across a clear blue sky.
Apartment in La Felce
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 favorite
A clear blue pool is seen in the foreground, reflecting the sky. In the background, a rustic stone building with a wooden door is positioned beside olive trees and rolling hills. The scene is framed by a few distant hills.
Apartment in Capannori
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.
Guest favorite
An inviting infinity pool is surrounded by lush greenery and trees, with several lounge chairs positioned nearby. A sun terrace provides ample space for relaxation, and a rustic stone building is visible in the background, complementing the serene outdoor atmosphere.
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

    $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

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