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Family-friendly holiday rentals in Certaldo

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Certaldo

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

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce
5 out of 5 average rating, 293 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favourite
Flat in Carmignano
4.97 out of 5 average rating, 232 reviews

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

Guest favourite
A scenic view unfolds from a terrace adorned with vibrant flower pots. Lush greenery and rolling hills stretch into the distance, framed by trees. The clear blue sky complements the picturesque landscape of vineyards and fields, creating a serene outdoor setting.
Home in Montespertoli
4.84 out of 5 average rating, 192 reviews

Sunny Beauty

Tranquillità - Bellezza - Relax. Siamo nel Chianti, San Gimignano, Firenze, Siena, Volterra e Pisa non sono lontane. Bellezza e cose straordinarie ci circondano, nonché buon cibo genuino, soprattutto ottimo vino e ottimo olio. Casa completamente ristrutturata. Nota: Ci potete trovare su Google maps. Negozi chiudano alle 20.00 Sono una guida turistica del territorio, ho studiato Arte e canto. Vi auguro un buon soggiorno a casa mia, arredata con amore e col obiettivo di farvi stare bene.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 202 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
The rustic exterior of the stone cottage features a traditional red-tiled roof and large arched windows. Lush greenery and flowering plants surround the building, while the rolling hills of Tuscany are visible in the background under a clear sky.
Flat in Poggibonsi
4.92 out of 5 average rating, 106 reviews

San Martino Cottage with large panoramic terrace

45 sqm apartment in San Martino ai Colli, located along Via Cassia and surrounded by beautiful Tuscan countryside. Perfect for those who want to visit the attractions of the area: San Gimignano, Monteriggioni, Chianti, Siena (20 min.), Florence (30 min.), Volterra (40 min.). 2 minutes from the Florence-Siena highway junction and close to the urban center of Poggibonsi and Barberino-Tavarnelle. The house has a large terrace where you can relax and admire the Chianti hills.

Top guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Flat in Poggibonsi
4.99 out of 5 average rating, 303 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

Guest favourite
A clear view of a swimming pool is presented, surrounded by a well-maintained grassy area. Sun loungers are positioned near the pool, with umbrellas providing shade. In the background, a building is visible, set among trees and shrubs, enhancing the serene landscape.
Apartment in Certaldo
4.84 out of 5 average rating, 101 reviews

Tenuta di Pomine Certaldo (Fi) Edera Apartment

Located on the 1st floor, 65 m2, spacious, bright, Tuscan-style furnishings consisting of a living room/kitchen, a double bedroom, a bedroom with two beds. Kitchenette (4-burner stove), oven, refrigerator, freezer, dishwasher. Bathroom with shower/sink/bidet/toilet, swimming pool (6x12 m.), shared washing machine on the ground floor, Wi-Fi. Terrace equipped with garden furniture, grill. Linen change once a week. There are two other apartments in the house

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 434 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Guest favourite
A spacious living area is depicted, featuring a dining table set with plates and cups. A comfortable sofa is positioned beside the table, and a staircase leads to the upper level. Natural light enters through the open terrace doors, providing a view of the outdoor area.
Apartment in Certaldo
4.79 out of 5 average rating, 117 reviews

In the center of Certaldo

The apartment is located in the heart of Certaldo, a small and quiet town nestled among the unmistakable Tuscan hills, just a 5-minute walk from the train station from where you can reach Siena or Florence, and also other cities, or by car. Certaldo has a unique medieval charm: the historic center in the upper part is beautifully preserved and from our apartment you can be reached on foot in a few minutes or by a panoramic funicular.

Guest favourite
The exterior of a two-story, Tuscan-style apartment is visible, featuring light-colored walls and traditional wooden shutters. A welcoming staircase leads to a balcony adorned with potted plants, providing access to the upper level. Greenery surrounds the entrance, adding to the tranquil ambiance.
Apartment in Gambassi Terme
4.89 out of 5 average rating, 245 reviews

A View Over Tuscany's Countryside

A quite and peaceful apartment in the middle of Tuscany countryside, ideal for 3 people also, is about 60 squares meters with bath , double bed , living room with a sofa' bed, kitchen and a beautiful terrace overlooking the vineyards.There is, also, a private parking inside the condominium and a nice bar near by. It is located near the main tourist attractions, this apartment is ideal for travelers who wants to explore Tuscany.

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 235 reviews

Casa al Gianni - Capanna

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

Top guest favourite
An aerial view captures the medieval village of Certaldo, featuring terracotta rooftops and winding streets. The lush greenery surrounding the village adds a natural touch, while historic buildings stand prominently, showcasing varied architectural styles. The placement of the highlighted property is evident within the quaint atmosphere.
Flat in Certaldo
4.98 out of 5 average rating, 125 reviews

House in a medieval tower with a view in Certaldo

Vacation home located in the heart of the medieval village of Certaldo. Second floor apartment without elevator consisting of kitchen with dining room, bedroom with plasma TV and terrace, bathroom with shower, bedroom with sofa bed, relaxation area and panoramic view. Large garden with barbecue! Sleeps 4. Free Wi-Fi!!!

Popular amenities for Certaldo family-friendly rentals

When is the best time to visit Certaldo?

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Avg. price$135 SGD$129 SGD$132 SGD$145 SGD$146 SGD$155 SGD$171 SGD$163 SGD$145 SGD$140 SGD$131 SGD$136 SGD
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Quick stats about holiday rentals that are family-friendly in Certaldo

  • Total holiday rentals

    Explore 30 holiday rentals in Certaldo

  • Nightly prices starting at

    Certaldo holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,380 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Certaldo holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Certaldo rentals

  • 4.8 Average rating

    Certaldo stays are highly rated by guests – averaging 4.8 out of 5!

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