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Family-friendly holiday rentals in Grassina

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Grassina

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 104 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 501 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Top Guest favourite
The image depicts the entrance to a Tuscan farmhouse, characterized by warm-colored walls and traditional architectural features. A wrought iron gate leads to a cobblestone path framed by lush greenery and potted plants, creating a welcoming entrance to the property.
Apartment in Bagno A Ripoli
4.95 out of 5 average rating, 114 reviews

Live in a farmhouse with a garden near the center

Surrounded by a very large garden, in a typical Tuscan farmhouse, just 6 km from the historic center of Florence, a stone's throw from Viola Park, the Nottolino is the ideal place for all those who want to visit Florence without giving up a holiday of tranquility and relaxation. The strategic location, the convenience of private parking, and the proximity to the Florence South toll booth make it perfect not only for discovering Florence, but also the villages of Chianti and the cities of Tuscany.

Top Guest favourite
A shaded terrace offers panoramic views of rolling hills and lush greenery, with terracotta rooftops visible in the foreground. The clear sky enhances the vibrant landscape, highlighting the rich textures of the countryside.
Home in Impruneta
4.98 out of 5 average rating, 182 reviews

Tiny romantic tower on the hills of Florence

Think of a tiny charming ancient tower, embedded in a time into a small XIX century tuscan villa on the florentine hills. Think of a romantic place for a couple, with a bedroom and a living room which opens onto a breathtaking terrace in the countryside, with a bathroom and a tiny kitchen. Also think that in 20 minutes drive you are into Florence downtown. Well, this is the place! To get all this you have to climb three flights of stairs with no lift. But you'll see it surely worth the effort.

Guest favourite
A bright and spacious living room features a large marble coffee table and a pair of elegant chaise lounges. A striking painting hangs above a contemporary white sofa adorned with colorful cushions. Antique furnishings and a patterned rug enhance the room's sophisticated ambiance.
Apartment in Centro
4.94 out of 5 average rating, 363 reviews

Museum Suite - Luxurious unit with a River View -

After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

Top Guest favourite
A dining area features a round wooden table surrounded by white chairs, with glasses and a bottle set upon it. Large open windows frame a view of the Ponte Vecchio and the Arno River, allowing natural light to brighten the space.
Apartment in Centro
5 out of 5 average rating, 373 reviews

[Ponte Vecchio] Charm and Awesome view of Florence

Make your stay unique and treat yourself to an experience that you will carry within you for a lifetime. Located in the heart of Florence, this magnificent apartment is the ideal solution for those looking for an exclusive and prestigious site to combine with a central location, which is perfect for easily visiting the main sites of interest, all reachable in less than 10 minutes by foot. The views are on Ponte Vecchio, and you can enjoy one of the most fascinating panoramas of the city.

Top Guest favourite
A historic building featuring a stone facade and architectural details reminiscent of medieval castles. The structure has several windows and a notable tower, with shops visible on the ground level. The image captures the building against a clear blue sky.
Apartment in Florence
4.99 out of 5 average rating, 154 reviews

Florence castle apartment [2 bedrooms,2 bathrooms]

Elegant accommodation in an historic building in medieval castle style, equipped with every comfort. Overlooking the Tuscan hills, in a quiet residential neighborhood very close to the historic center. Well connected by public transports and 20 minutes walk from the main monuments. Outside the caos of the historic center, you will be into the authentic Florentine life. Downstairs you will find an excellent and elegant pastry shop, groceries, typical trattorias and a big supermarket.

Guest favourite
A lush garden surrounds the farmhouse, featuring a winding brick pathway lined with vibrant greenery and colorful flowers. Mature trees provide shade, and a variety of plants contribute to a serene atmosphere, enhancing the natural beauty of the outdoors.
Condo in Strada In Chianti
4.95 out of 5 average rating, 409 reviews

Chianti Apartment in 12th Century Tuscan farmhouse

Your separate apartment in our secluded 12th century farmhouse has its own entrance and is on two levels; kitchen and sitting area is on the first floor, beds and bath are upstairs. The large fireplace in the kitchen is very typical in these old houses. In the sleeping rooms we have air conditioning. The garden is unique , a place to relax and enjoy. If there is no available date check out our second new listing, same property, "Chianti Patio Apartment" Pleased to welcome you!

Top Guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 218 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top Guest favourite
The kitchen area features wooden cabinetry and a dining table surrounded by chairs. A traditional chandelier hangs from the ceiling. The room includes a stove, sink, and a television on a wooden sideboard, with decorative items and local artwork adorning the walls.
Home in Bagno A Ripoli
4.94 out of 5 average rating, 126 reviews

Casa Nespolo – Cozy farmhouse in Chianti

This house is part of an old building recently refurbished and in the past was a convent which used to be a part of the castle estate located in front of us. The interior design reflects the typical Tuscan style of furniture and materials. The kitchen is equipped with a fridge, microwave, coffee machine, sink and utensils. Available daily, for breakfast you will find coffee/tea, milk, biscuits and cakes. IT'S RECOMMENDED TO HAVE A CAR TO REACH THE HOUSE!

Top Guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 133 reviews

Tower Penthouse in small castle near Florence

900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Top Guest favourite
The image showcases a rustic stone farmhouse surrounded by lush vineyards and olive trees. The building features a classic roof with terracotta tiles, set against a clear blue sky. Green grass frames the scene, emphasizing the natural beauty of the countryside.
Villa in Impruneta
4.99 out of 5 average rating, 114 reviews

Podere Scaluccia Chianti Agritourism, Florence

The farmhouse is located 15 minutes (8 km) from the center of Florence, a city rich in art and culture, and is surrounded by beautiful panoramic views of the hills, at the entrance to Chianti. The house is old: traditional materials such as stone, wood and terracotta are the main features. The outdoor garden is available to everyone! To learn more, search for Podere Scaluccia

Popular amenities for Grassina family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Grassina

  • Total holiday rentals

    Explore 30 holiday rentals in Grassina

  • Nightly prices starting at

    Grassina holiday rentals start at $191 NZD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Grassina holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grassina rentals

  • 4.7 Average rating

    Grassina stays receive an average rating of 4.7 out of 5 from guests