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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
5 out of 5 average rating, 305 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.

Guest favourite
Flat
4.96 out of 5 average rating, 244 reviews

Casa Irene

Casa Irene is a delightful Tuscan-style apartment, located on the second and top floor of a building just a 5-minute walk from the center, 50 meters to Porta San Matteo and another 50 meters to Via Francigena. Given the secluded location, it is easily reached by car to park in the immediate free parking. The apartment equipped with WiFi and air conditioning is divided into an open space living room/kitchen, bedroom and bathroom with shower and a large terrace overlooking the walls of San Gimignano

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home
4.96 out of 5 average rating, 116 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home
4.99 out of 5 average rating, 134 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

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
5 out of 5 average rating, 203 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 image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Top guest favourite
A serene landscape showcases a rustic stone building surrounded by tall cypress trees, offering a touch of greenery to the well-maintained lawn. The backdrop reveals gentle hills under a clear blue sky, creating a peaceful countryside atmosphere.
Farm stay
4.99 out of 5 average rating, 469 reviews

Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

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
4.78 out of 5 average rating, 120 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 away you will find 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 in fact beautifully preserved and from our apartment you can reach it on foot in a few minutes or with 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
4.89 out of 5 average rating, 247 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
4.91 out of 5 average rating, 241 reviews

Casa al Gianni - Hut

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
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£75£73£74£81£82£87£96£92£81£86£80£84
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

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 £37 per night before taxes and fees

  • Verified guest reviews

    Over 1,420 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

    30 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!