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Family-friendly vacation rentals in Guardistallo

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Guardistallo

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

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Home in Galluzzo

4.88 out of 5 average rating, 766 reviews

TREEhouse/casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the Duomo and 30' from Siena. Come and live with us; enjoy our olive trees, the kitchen garden and our family life style away from the working rhythm. By providing wifi only in the communal courtyard we suggest our guests to utilize internet only when is really needed. Taking a break from been connected with elsewhere and enjoy the 'here and now' could be our best present to you!

Castle in Montecatini Val di Cecina

4.99 out of 5 average rating, 102 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here with our sons and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Home in Peccioli

4.99 out of 5 average rating, 121 reviews

A breathless view

Placed halfroad between Florence and Pisa this Airbnb has a large terrace and a hanging garden. All of this is set against a backdrop of endless hills. It is like a living and eternal painting, where one is not a spectator but an actor and part of a film scene. Being North East here every morning the sun appears on the horizon behind the last strip of green hills while white brushstrokes of mist melt into the air as the red ball rises into the sky. It is a sight that takes one's breath away.

Cottage in Chianni

4.98 out of 5 average rating, 140 reviews

La Pietruzza - The Private Chalet with a Soul -

Detached country cottage (in exclusive use) in stone and glass dating from XVIII century ideal for 4 persons. Wide wooden veranda. EXCLUSIVE POOL with SALTED WATER ( 33 ft x 16.40 ft ) depth of the pool from 4.6 ft to 7.9 ft. The Chalet is surrounded by 6000 meters of land with fruit trees, olive trees, acacias. We care about nature and do not use herbicides. There is no gas at home because it is all electric with photovoltaic system. (CIR O5OO12LTNOOO3 - CIN IT050012C2LZ3CHRNQ)

Rental unit in Castelnuovo della Misericordia

4.93 out of 5 average rating, 471 reviews

RENOVATED apartment, 75 sqm 10min from the sea.

Ideal for a family holiday, the apartment is about 10 km (10 minutes) from the sea and is located on the second floor of a small building where we also live, measuring about 75 square meters and is completely renovated. Consisting of a small entrance, 2 large bedrooms, a kitchen, a bathroom and a closet, it is very comfortable, bright and spacious. Bus stop about 20 meters, pharmacy, supermarket and other services ALL within walking distance, restaurants in the area

Cottage in Ponte Feccia

4.95 out of 5 average rating, 152 reviews

Country cottage C&M surrounded by green love Tuscany

Country cottage in stone , independent in the Tuscan countryside in the province of Siena ,with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main villages of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena , Monteriggioni , an hour from Florence and 30/40min from the sea. Only 20 minutes from the beautiful Terme del Petriolo .

Rental unit in Cecina

4.93 out of 5 average rating, 216 reviews

Cozy apartment in Cecina

45 sqm apartment arranged on a single floor with small garden that can be used for lunches and dinners outdoors. It includes: a living room with a sofa bed and kitchen, a bathroom and a bedroom. In the residential area of Cecina, 10 minute drive to sea. Parking is free on the entire street of the apartment. The apartment is 15 minutes walk from Cecina train station. Bus stop 2 minutes on foot. There are two bicycles available for guests.

Farm stay in Simignano

4.88 out of 5 average rating, 156 reviews

Casa al Gianni - Hut

Hi, we are Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our brand is simple living in close contact with the nature and animals of our farm. Nestled in the woods and the beautiful Tuscan countryside you will spend an unforgettable holiday. This corner of paradise will remain in your heart!

Villa in Castagneto Carducci

4.99 out of 5 average rating, 104 reviews

sea view villa with private infinity pool

RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Farm stay in Pisa

4.99 out of 5 average rating, 276 reviews

Closing estate in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Rental unit in Centro Storico

5 out of 5 average rating, 469 reviews

Renaissance Apartment with Duomo Views!

I decorated the apartment so that guests could experience the great age of the Florentine Renaissance with their own skin. The environment is full of details and decorations. For the Florentine Baroque decoration see my listing: Duomo, Baroque&Renaissance on the Roof!

Rental unit in Montescudaio

4.79 out of 5 average rating, 102 reviews

Casetta Sole with view over Tuscany Hills and Sea

A cozy apartment made by a careful renovation of an old family winery, that's why it is so cool in the summer and warm in the winter. Simply furnished respecting the taste of a Tuscan mansion. Close to Pisa Volterra Bolgheri Lucca Siena SanGimignano

Vacation rentals for every style

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Popular amenities for Guardistallo family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Condo in Centro Storico

4.97 out of 5 average rating, 438 reviews

What a view in Florence heart!

Rental unit in Sassetta

4.89 out of 5 average rating, 133 reviews

Apartment Alex-Tuscany Charme

Rental unit in Centro Storico

4.93 out of 5 average rating, 273 reviews

M&G Apartment your home away from home

Villa in San Casciano in Val di Pesa

4.94 out of 5 average rating, 158 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

Rental unit in Gavinana

4.96 out of 5 average rating, 391 reviews

Suite Michelangelo with Terrace

Condo in Casole d'Elsa

4.93 out of 5 average rating, 142 reviews

La Casetta

Loft in Centro Storico

4.96 out of 5 average rating, 421 reviews

Little Jewel Florence , Dome, David, - Garage

Condo in Morrona

4.97 out of 5 average rating, 123 reviews

Casa Luna-Splendida overlooking the pool and Tuscan nature

Family- and pet-friendly home rentals

Townhouse in Scandicci

4.87 out of 5 average rating, 276 reviews

Florence Country Side: Giogoli a place to be!

Condo in San Gimignano

4.95 out of 5 average rating, 123 reviews

Adalberto Apartment inside the Manor of Fulignano

Rental unit in Centro Storico

4.97 out of 5 average rating, 270 reviews

home away from home, to make you feel at home

Condo in Centro Storico

4.99 out of 5 average rating, 104 reviews

Asso's Place, Luxury Apartment with stunning view

Cottage in San Casciano in Val di Pesa

4.81 out of 5 average rating, 156 reviews

Chianti Independent Barn

Rental unit in San Gimignano

4.97 out of 5 average rating, 108 reviews

Apartment at ground floor with garden

Farm stay in Provincia di Siena

4.98 out of 5 average rating, 173 reviews

Agriturismo La Villa - Il Castagno, Pool & Garden

Rental unit in Centro Storico

4.97 out of 5 average rating, 232 reviews

Wonderful house with garden

Family-friendly home rentals with a pool

Rental unit in Castellina in Chianti

4.97 out of 5 average rating, 102 reviews

Visit Chianti, Siena, S.Gimignano, Florence

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 186 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Farm stay in Castelfiorentino

4.93 out of 5 average rating, 140 reviews

Amazing view, pool and relax, 5+2

Rental unit in Empoli

4.91 out of 5 average rating, 469 reviews

FIENILE VILLACOLLE Tuscan hill

Farm stay in Lastra a Signa

4.96 out of 5 average rating, 197 reviews

Cozy Room in Tuscany

Home in Volterra

4.93 out of 5 average rating, 176 reviews

Podere Collina

Home in Localita' Pievescola

4.94 out of 5 average rating, 168 reviews

Antico Borgo Ripostena – no. 8 Casa Vecchia

Villa in Montespertoli

4.93 out of 5 average rating, 166 reviews

Colonica in the Chianti

Quick stats about vacation rentals that are family-friendly in Guardistallo

Total rentals
110 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
860 reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore