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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
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 stars2 weeks 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 stars2 weeks 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, 300 reviews

M&G Apartment your home away from home

NorhusnaRating, 5 stars1 day ago
Beautiful and cosy place located at a convenient location. We enjoyed our stay. Highly recommended!
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 stars3 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!
Guest favorite
A rustic two-story structure is framed by lush greenery, showcasing stone and brick elements. Windows are adorned with decorative iron bars and window boxes, adding character. The inviting exterior is complemented by a blue sky and gentle hillside, creating a serene countryside setting.
Home in Rignano sull'Arno
4.94 out of 5 average rating, 119 reviews

LA CASA DELL' AMBRA-ANCIENT BARN RENOVATED-

BrooklynRating, 5 stars3 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
A spacious living area features terracotta flooring and wooden beams, complemented by large windows allowing natural light. A dining table accommodates several guests, while a comfortable sofa and armchair provide seating. Artwork adorns the walls, enhancing the modern yet welcoming environment.
Condo in Centro Storico
4.89 out of 5 average rating, 111 reviews

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

DenizRating, 5 stars2 weeks 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
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 stars2 weeks 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.
Superhost
An exterior view of a rustic house showcases a spacious patio surrounded by lush greenery. Potted flowers and plants line the wooden fence, enhancing the inviting atmosphere. A gazebo can be seen on the patio, providing shade for outdoor relaxation.
Home in Borgo San Lorenzo
4.83 out of 5 average rating, 310 reviews

Country house in Mugello

Ubaid UrRating, 5 stars2 weeks ago
Lucrezia is a great person and she welcomed us at the entrance. We had a pleasant and peaceful stay. The only thing I would highlight is to be careful of any consumables as most of the stuffs expired many years ago and she still kept it, I don’t know for what reasons.
Superhost
A serene pool reflects the vibrant colors of the sunset, with gentle waves suggesting a peaceful ambiance. Lush greenery surrounds the area, creating a natural setting. The silhouette of a building and a lone tree can be seen in the background against the colorful sky.
Home in Staggia
4.87 out of 5 average rating, 39 reviews

Holiday in the Chianti Senese

JosefinRating, 5 stars9 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.
Guest favorite
A spacious bedroom features a comfortable bed with a textured blanket. Large windows offer natural light, framed by teal curtains. Two framed artworks adorn the wall above the bed, adding a touch of elegance to the room.
Apartment in Lastra a Signa
5 out of 5 average rating, 54 reviews

Only long term apt in a 17 century FARM

SarahRating, 5 stars7 months ago
Magical stay at Paola's. Hard to describe in a few words all the kindness she showed us, we immediately felt at home. Paola picked us up by car at the train station and welcomed us with a nice bottle of wine and pizza - delicious - hard to have a better arrival especially after a long journey. She was very proactive throughout our stay and even took us half a day to Chianti so we could visit a vineyard because we didn't have a car - we still can't believe her generosity! She is very attentive to all her guests and her property is beautiful, we enjoyed the pool and the apartment is wonderfully well decorated and equipped. We highly recommend staying at Paola's, the best Airbnb host we've ever had. Thanks again for everything Paola, you've been wonderful, and we're already dreaming of coming back! Arrivederci! :)
Top guest favorite
Vacation home in Panzano
4.97 out of 5 average rating, 144 reviews

Fienile Santa Teresa

CiroRating, 5 stars1 week ago
John and Christine are amazing hosts! The place is wonderful! Highly recommended!!
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 serene outdoor area features a swimming pool with clear blue water, bordered by wooden decking. Four lounge chairs face a vibrant garden of yellow flowers, offering expansive views of the surrounding hills and sky filled with fluffy clouds.
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 238 reviews

House between Firenze, Arezzo, chianti e Siena

IainRating, 5 stars6 days ago
What a hidden gem! It is exactly what you think of when it comes to an authentic Italian household! The pictures do not do it justice, the views are incredible! Every morning we were treated to a cloud inversion over the valley, it was jaw droppingly good! The food in the restaurant was top notch and reasonably priced also! The family are super friendly and would always greet us and go out of their way to have a conversation which made us feel really welcomed! The farm just down by the pool area is such a nice touch and the local dog Franchi is such a good boy too 😃 We would have loved to do the day trip with the family but we didn't have enough time as we were only there for 2 nigjt! We highly recommend staying here and would 100% go back in a heart beat!
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!

Family-friendly home rentals with a pool

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
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.
Top guest favorite
Farm stay in Castelfiorentino
4.93 out of 5 average rating, 147 reviews

Amazing view, pool and relax, 5 adults

JenniferRating, 5 stars1 month 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
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!
Top guest favorite
The spacious pool is surrounded by a sun terrace, featuring a clear blue surface that reflects the sky. Sun loungers and umbrellas are positioned nearby, framed by lush greenery and foliage, creating a relaxing outdoor environment.
Apartment in Montespertoli
4.89 out of 5 average rating, 19 reviews

Cozy Apart. in Cottage,4/5people,SWPOOL,AIRCO,WIFI

CristinaRating, 5 stars8 months ago
Wonderful place and Nicola was a fantastic host. The pictures were spot on. Nicola went above and beyond for us. Great recommendations and suggestions on where to go/ restaurants to try out. He was super helpful when a family member needed medicine and he was very responsive with finding an open pharmacy. I would absolutely recommend this place to anyone wanting peace and quiet with beautiful views of the vineyards. I will be back.
Top guest favorite
Villa in Certaldo
4.89 out of 5 average rating, 144 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
A circular pool is set within a natural landscape, surrounded by olive trees. The pool has a light blue hue, with a stone-tiled edge. A lounge chair is positioned nearby, adding to the outdoor relaxation space.
Home in Florence
4.9 out of 5 average rating, 155 reviews

Il Melograno, Florence hills & pool & olive oil

ThomasRating, 5 stars1 week ago
Lovely countryside place to stay. Host was extremely flexible for when we had a really late check-in as our train got cancelled. Would recommend.
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 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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