
Family-friendly vacation rentals in Grassina
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Top-rated family-friendly rentals in Grassina
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Popular amenities for Grassina family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi
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!

Holiday House "The Seasons of Bacchus"
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👍🏼

CASA AL BOSCO 1
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!

Charming estate with views
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!

M&G Apartment your home away from home
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!

The Vichiaccio Villa with Jacuzzi in Chianti
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

LA CASA DELL' AMBRA-ANCIENT BARN RENOVATED-
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!

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

Within walking distance of the center and away from the chaos
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.

Country house in Mugello
Nice accommodation, worth it.

Holiday in the Chianti Senese
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.

Comfortable house Greve in Chianti
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.

Fienile Santa Teresa
Very private and peaceful. Beautiful view and the house was well equipped and comfortable. Host was very responsive and helpful.

APARTMENTS 3 people + 4 people
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!

House between Firenze, Arezzo, chianti e Siena
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.

loft in the heart of Tuscan Chianti
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

Tuscan Villa with Privacy,Pool,near towncentre
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!

Margherita
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!

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.

Amazing view, pool and relax, 5 adults
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.

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!

Tuscan farmhouse with private pool and views
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.

Il Melograno, Florence hills & pool & olive oil
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

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2
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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- Duomo di Firenze
- Ponte Vecchio
- Teatro Verdi
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Basilica of Santa Maria Novella
- Uffizi Gallery
- Piazzale Michelangelo
- Parco delle Cascine
- Mercato Centrale
- Stadio Artemio Franchi
- Pitti Palace
- Santa Maria della Scala
- Basilica di Santa Croce
- The Boboli Gardens
- Pinocchio Park
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Vecchio
- Teatro Tuscanyhall
- Piazza della Repubblica
- Teatro della Pergola
- Podere La Marronaia, Sosta alle Colonne
- Palazzo Medici Riccardi