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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, 303 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 in San Gimignano
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
Lush green hills are interspersed with orderly rows of olive trees, leading to a charming rustic building. In the distance, the silhouette of San Gimignano's historic towers is visible against a clear blue sky, creating a scenic view of the Tuscan landscape.
Farm stay in San Gimignano
4.9 out of 5 average rating, 229 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

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 in San Casciano In Val di Pesa
4.98 out of 5 average rating, 220 reviews

Sunset on Chianti Classico

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
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, 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
An outdoor space features a large swimming pool surrounded by lush greenery and olive trees. Sun loungers are arranged around the pool, and striped umbrellas provide shade. The view includes gently rolling hills, contributing to a serene environment.
Farm stay in Castelfiorentino
4.91 out of 5 average rating, 136 reviews

Apartment in Agriturismo with pool and great view

L'appartamento, facente parte di un agriturismo è arredato in stile tipico , tutto interamente rinnovato , composto da camera matrimoniale, cucina , bagno e divano letto doppio nella cucina; situato nel centro della Toscana è un ottimo punto di partenza per poter visitare la regione; a 20 minuti da San Gimignano e 35 da Firenze. E' adatto ad una coppia o ad una famiglia con figli piccoli avendo come soluzione per la terza e la quarta persona un unico divano letto matrimoniale.

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 in Barberino Tavarnelle
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.

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
4.78 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.

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, 446 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
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, 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.

Guest favourite
A serene outdoor space features a sparkling swimming pool bordered by a smooth red tile deck. Sun loungers and umbrellas are positioned beside the pool. Lush greenery and blooming plants surround the area, enhancing the view of the distant hillside and a charming villa.
Flat in Certaldo
4.89 out of 5 average rating, 117 reviews

Tenuta di Pomine Certaldo (FI) Papavero Apartment

Three-room apartment 65 m2 on the first floor. Tasteful furnishings: 1 double bedroom, 1 bedroom with two beds, kitchen (4 hotplates), oven, refrigerator, freezer, dishwasher, microwave, TV, Wi-Fi. Bathroom with shower, sink, bidet, toilet. Beautiful panoramic views of the countryside. Linen change/week. Accommodation tax of €2 per day per person to be paid upon arrival for the first 6 days (from 14 years of age)

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$131 SGD$126 SGD$128 SGD$141 SGD$142 SGD$151 SGD$166 SGD$159 SGD$141 SGD$150 SGD$138 SGD$146 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 $64 SGD 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!

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