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Family-friendly vacation rentals in Grassina

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Grassina family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Cottage in San Casciano In Val di Pesa
4.95 out of 5 average rating, 137 reviews

Il Fienile, Cottage in the country with Jacuzzi

JaimeeRating, 5 stars1 week ago
We loved our visit to Massimo's home. We stayed in this home during our Tuscany tour. Beatrice allowed us to leave our luggage before check in which was very convenient as we didn't want to leave them in the car during our visit to Siena. While it was a bit far from places like Pienza and Cortona (about 1 1/2 hours), it was incredibly convenient to our car drop off in Florence and our visits to Siena and San Gimignano. I HIGHLY recommend using the link they send to arrive. I once simply typed in the address and Google Maps took me to three locations in San Casciano (one up a very steep mountain!) before I remembered that I had a different link. I can't say enough about relaxing in a hot top over looking the vineyards as the sun sets. You should definitely pay the extra cost!
Guest favorite
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 favorite
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
Home in Gaiole in Chianti
4.86 out of 5 average rating, 254 reviews

Charming estate with views

BriRating, 5 stars1 day 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
Apartment in Centro Storico
4.94 out of 5 average rating, 297 reviews

M&G Apartment your home away from home

DonielleRating, 5 stars1 week ago
Our stay in Florence was incredible thanks to Max’s hospitality. The property was very secure, walkable to all of Florence’s beautiful surroundings. Near a park, which was perfect for my children. He included great local recommendations, offered to arrange car services, and even included some wonderful family history with our checkin. The space is gorgeous and convenient. Would absolutely stay here again and again!
Guest favorite
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 stars2 weeks ago
Lovely place where I stayed with my friends. We all had a good time because the house is equipped with all amenities both in the kitchen and in the bedrooms. A magical place
Guest favorite
Home in Rignano sull'Arno
4.94 out of 5 average rating, 119 reviews

LA CASA DELL' AMBRA-ANCIENT BARN RENOVATED-

BrooklynRating, 5 stars2 weeks ago
If you want a peaceful, Tuscan stay with panoramic picturesque views, then this is your place! We were welcomed with homemade cakes, bread, and wine! After a long day of travel this perk was so appreciated. Our stay was perfect! After a long day of walking and driving to either Lucca, San Giminagno, Chianti Classico or Florence the hot tub relaxed our achy legs. The beds were comfortable and the showers were hot. We loved this home so much that we hope to return with our families in the future! This home made our visit to Italy PERFECTO!
Guest favorite
Condo in Centro Storico
4.89 out of 5 average rating, 111 reviews

Fortress Area, Attic with Terrace, Jacuzzi, A/C

DenizRating, 5 stars6 days ago
We had a lovely stay at this apartment. The location is very central, about a 15-minute walk to the train station and just 10–15 minutes to major attractions like the Uffizi Gallery. The apartment was clean and had all the basic essentials we needed for a comfortable stay. The little garden was a sweet bonus, perfect for a quiet moment after a day of exploring. The hosts were also very kind and flexible, allowing us to leave our luggage after check-out, which we really appreciated. Highly recommended for a convenient and cozy stay in Florence.

Family- and pet-friendly home rentals

Guest favorite
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 Borgo San Lorenzo
4.82 out of 5 average rating, 308 reviews

Country house in Mugello

MauroRating, 5 stars2 weeks ago
Nice accommodation, worth it.
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
Home in Greve in Chianti
4.74 out of 5 average rating, 129 reviews

Comfortable house Greve in Chianti

CarlRating, 5 stars6 months ago
Our stay here was perfect! It is such a lovey Tuscan place that made us feel right at home. It is a short 10 minute walk from the center of Greve and it provides lovely views of the surrounding areas. Luana is very kind and quick to respond to our questions. We highly recommend this place for future guests! The only advice we can give for guests staying anywhere in Tuscany is to pick up some mosquito spray - they are everywhere.
Top guest favorite
Vacation home in Panzano
4.97 out of 5 average rating, 141 reviews

Fienile Santa Teresa

MarnieRating, 5 stars5 months ago
Very private and peaceful. Beautiful view and the house was well equipped and comfortable. Host was very responsive and helpful.
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
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 236 reviews

House between Firenze, Arezzo, chianti e Siena

JimRating, 5 stars3 days ago
We loved Oscar's place. The restaurant was fantastic for breakfasts and dinners. The property was beautiful. This would be a special place for small wedding! The pool was inviting too! It was a pleasant surprise to meet all of their animals! 2 horses, 2 pigs, ducks, goats, sheep, chickens. rooster, cats and 2 dogs! We had excellent wine with amazing food while watching gorgeous sunsets. Oscar's and family are it easy and comfortable.
Superhost
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.

Family-friendly home rentals with a pool

Superhost
Home in Volterra
4.88 out of 5 average rating, 49 reviews

Tuscan Villa with Privacy,Pool,near towncentre

RachelRating, 5 stars19 months ago
We had a quick 36 hour stop here during our honeymoon trek though Italy and Sara’s place was a great place to reset and relax for a bit. We loved visiting Volterra (relatively tourist free compared to our other stops) and the guest villa we stayed in was very cozy and comfortable. Sara and her husband were very helpful with anything we needed and they even left us a bottle of champagne on our last night!
Superhost
Farm stay in Montaione
4.86 out of 5 average rating, 7 reviews

Margherita

SusanneRating, 5 stars8 months ago
We had a lovely time with Cristiana and Sergio. The apartment "La Margherita" was very clean and spacious. The children enjoyed the pool and there was plenty of room for everyone. We received helpful tips and Cristiana was always open to questions and responded very quickly. For chess lovers, there is a beautiful board in a great location. Highly recommended!
Guest favorite
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.
Top guest favorite
Farm stay in Castelfiorentino
4.93 out of 5 average rating, 146 reviews

Amazing view, pool and relax, 5 adults

JenniferRating, 5 stars3 weeks ago
I had tears of joy upon arrival. This home is exactly what you dream of in Tuscany. It is nestled on a hill with beautiful gardens, amazing sunrises and sunsets, a private outdoor table space and you can hear the birds singing all around you. The house had a private gated yard with parking that makes you feel safe. The home has so much Italian charm. It was a little cold during our stay in March, but there was lots of extra blankets to use at night and access to firewood. I would love to return in the summer to see the vineyards and use the pool. Everything was wonderful, including our very welcoming hosts.
Top guest favorite
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!
Top guest favorite
Villa in Certaldo
4.89 out of 5 average rating, 143 reviews

Tuscan farmhouse with private pool and views

DorothyRating, 5 stars6 months ago
Fantastic accommodation with lovely views of the countryside. Especially loved the fire place and large spacious kitchen. Charley and Ann were very gracious hosts and I would have no problem recommending this accommodation to anyone who wants to visit Tuscany. The accommodation was within 30 mins of most tourist towns and trains which made it excellent for day trips.
Superhost
Home in Florence
4.9 out of 5 average rating, 153 reviews

Il Melograno, Florence hills & pool & olive oil

LorenzoRating, 5 stars3 months ago
The place is stunning. Wonderful cozy and private house in the middle of the Tuscany hills, just 10' away from Florence historical city centre. Perfect for families with small children or young couples. Beniamino is a wonderful host, always responsive and ready to help. We had a wonderful time
Guest favorite
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 Grassina

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    620 reviews

  • Rentals with a pool

    30 properties have a pool

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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