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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 :)
Superhost
A charming house is framed by lush greenery, with several trees dotting the manicured lawn. The exterior features warm tones, complemented by a covered porch area. Various plants provide a natural ambiance, enhancing the serene outdoor space.
Home in Montespertoli
4.84 out of 5 average rating, 116 reviews

I Limoni Apartment in Tuscany

FrancescaRating, 5 stars1 day ago
We spent a few days with the family in this wonderful property. The host was very nice; she recommended some great places to eat and was always accommodating to every request. The property was wonderful with truly priceless views. I highly recommend it
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 stars2 days 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 stars4 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, 170 reviews

Within walking distance of the center and away from the chaos

MonikaRating, 5 stars1 week ago
Stefania was very welcoming and easy to communicate with. Her home is in a nice area away from the crowds. We chose to walk into the centre but there is a bus station close by.
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.
Guest favorite
Farm stay in Bucine
4.98 out of 5 average rating, 43 reviews

Boggina. Private villa with pool, walk to village

AnnaRating, 5 stars8 months ago
Boggina was such a beautiful setting for our two families. There is no air conditioning, but the house kept beautifully cool by using the shutters in the day and using fans at night. The bedrooms were dreamy, full of trinkets from families past. The pool was fantastic and we enjoyed a lovely wine tasting tour! We basically didn’t want to leave! Many thanks team Marco 😊
Guest favorite
Cottage in Bagno A Ripoli
5 out of 5 average rating, 29 reviews

Borgo Spedaletto 3 – Dolcevita Holiday

MathewRating, 5 stars4 days ago
Charming little cottage perfect for a small family in the hills near Florence. Had everything we needed. About 25 minutes drive through the country to central Florence so perfect for day trips in. Lovely walks in the olive groves around the cottage.
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 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 stars1 week 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!
Guest favorite
The exterior of a restored stone house is showcased, featuring natural stone walls adorned with potted plants and flowers. A wooden bench sits invitingly near the entrance, and a soft curtain sways in the light breeze, adding a touch of charm to the peaceful setting.
Home in Casamona
4.87 out of 5 average rating, 142 reviews

Stone Cottage in Tuscan Countryside

BasRating, 5 stars2 weeks ago
Great stay and great host!

Family-friendly home rentals with a pool

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.
Guest favorite
A scenic view of a stone house surrounded by greenery shows a shared pool area with sun loungers and an umbrella. Olive trees dot the landscape, providing a serene backdrop of the Tuscan countryside.
Hut in Poggibonsi
4.94 out of 5 average rating, 129 reviews

Lovely barn with pool between Siena and Florence

JamieRating, 5 stars6 months ago
Great stay here during our time in Tuscany. The roads can be as you approach Michele's place so definitely recommend a small suv or something like that. Michele's was very friendly and flexible on things and even brought us a few things to do laundry with. There are two sweet cats that live on the property and one will come and greet you every morning if you're nice to it. We stayed here while spending time in Florence, Siena and the town of Poggibonsi is about 15 minutes away if you need groceries or a close dinner.
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
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 stars2 weeks 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!!
Guest favorite
A serene pool with a smooth surface reflects the surrounding greenery. Tall cypress trees and lush garden areas border the pool, complemented by colorful plants and a well-maintained lawn. The sky is bright and clear, adding to the tranquil ambiance of the outdoor space.
Home in Cerbaia
4.9 out of 5 average rating, 21 reviews

Villanuova Power 2

AndrewRating, 5 stars8 months ago
Great location - close if you are flying into/from the Florence airport - extremely close to to Villa Antinori - Dario Ceccini in Panzano - San Gimignano - Siena, etc. Pictures are representative of the apartment - grounds exceed the pictures. Grounds are very well maintained. The pool is exceptional. Great cats and dogs to welcome you throughout the day. Kitchen is very workable, knives are sharp, gas stove and kitchen utensils are stocked and ready for your carbonara or amatriciana. Plenty of staff is located on premises but are not at all intrusive. 11 out of 10. Will return.

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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