
Family-friendly holiday rentals in Certaldo
Find and book unique family-friendly homes on Airbnb
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 $71 AUD per night before taxes and fees

Verified guest reviews
Over 1,540 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Certaldo holiday rentals include Wi-Fi 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!
Top-rated family-friendly rentals in Certaldo
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!
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Cosy Tuscan Home near Florence & San Gimignano
A WELCOMING NEST where tradition and modern comfort come together. Perfect for those who want to slow down, relax and experience the most authentic Tuscany, away from the hustle and bustle. Imagine waking up in the heart of a Tuscan village, looking out over the square and starting your day in the peace and quiet of the local way of life. The apartment, which has been fully renovated and tastefully furnished, is located in the historic centre of Gambassi Terme, an ideal base for exploring the wonders of Tuscany.
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Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience
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Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.
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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.
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
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Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
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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.
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Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷
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Green Dome @ The Land Before Time Retreats
Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.
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A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.
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Paluffo Stillo House
Paluffo is an historic 15th century building restored in 2010 conserving its original structure and design. Stillo house features a spacious living room with dining room and a fireplace, 2 bedrooms and 1 of them has a loft with a single bed, 2 bathrooms, a big kitchen, and a private garden with a wonderful view of the Chianti hills.
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Popular amenities for Certaldo family-friendly rentals
Family-friendly home rentals with a hot tub

SuiteLouise.pool, Hot Tub,homeGym & private Garden
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Typical Tuscan country house
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La Cipressina Relax in Tuscany
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Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
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Il Fienile, Cottage in the country with Jacuzzi
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I Limoni Apartment in Tuscany
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Country House w/ heated Pool near the City Centre
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Barrel Suite Tuscany • Hot Tub • Vineyard View
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Family- and pet-friendly home rentals

Villa Il Vecchio Pozzo in Tuscany
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Florentine Hills 'Le Scalette'
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Historic house in heart of Tuscany
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Beautiful medieval village!!!
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Vittoria Chianti Vacations 🍇🍷
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TREEhouse / casaBARTHEL
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Suite in Castello di Valle
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Private villa/swimming pool in Tuscany
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Family-friendly home rentals with a pool

Relaxation and charm in the Chianti hills
HospitalityLocationViewDecorIndoor spacesPoolFamilyCleanlinessOutdoor spacesComfortNearbyKitchenGetting aroundQuietBreakfastAmenitiesConditionWalkabilitySleep qualityAccuracyBathroomCheck-inWi-FiParkingAir conditioningTVLayoutLong stayBackyardValueBiking

Cercis - La Palmierina
ViewHospitalityLocationPoolCleanlinessFamilyGetting aroundKitchenAmenitiesIndoor spacesNearbyComfortAccuracyQuietDecorShared spacesCheck-inOutdoor spacesBathroomSleep qualityAccessLaundryConditionNoiseParkingValueParksWi-FiWalkabilityLong stayBeachCheckout

Tenuta di Pomine Certaldo (FI) Papavero Apartment
LocationPoolViewHospitalityGetting aroundCleanlinessOutdoor spacesQuietNearbyIndoor spacesAccuracyFamilyAir conditioningKitchenComfortSleep qualityAmenitiesLaundryConditionBathroomWalkabilityAccessShared spacesValueCheck-inDecorWi-FiParkingBreakfastBarbecueParksNoise

Infinity pool in Chianti 1
HospitalityPoolViewLocationFamilyNearbyOutdoor spacesIndoor spacesCleanlinessKitchenWalkabilityGetting aroundAmenitiesDecorAccuracyComfortAir conditioningWi-FiSleep qualityCheck-inBathroomBarbecueLayoutConditionShared spacesQuietLaundryBackyardTVParkingBeachCheckoutValue

Podere La Castellina - No. 1 COTTAGE
HospitalityLocationPoolViewFamilyGetting aroundComfortCleanlinessNearbyDecorIndoor spacesConditionAccuracyQuietKitchenAmenitiesOutdoor spacesBarbecueSleep qualityBreakfastShared spacesAir conditioningBathroomWi-FiParksHikingHeatingLaundryWalkabilityLong stayBeachAccessValue

The Castle of Ferrano - Castle in Tuscany
HospitalityLocationViewPoolOutdoor spacesGetting aroundIndoor spacesComfortKitchenCleanlinessDecorNearbyQuietAmenitiesFamilyAccuracySleep qualityBathroomWi-FiWalkabilityAccessParkingConditionHikingAir conditioningLong stayBreakfastTVBarbecueHeatingValueBikingCheck-in

Belforti Tower
HospitalityViewLocationOutdoor spacesNearbyPoolIndoor spacesFamilyGetting aroundComfortCleanlinessKitchenWalkabilityDecorSleep qualityBathroomAmenitiesWi-FiConditionBreakfastAccuracyHikingParkingHot tubNoiseAir conditioningPetsBarbecueLayoutLaundryBeachAccessValueCheck-in

Private Chianti Cottage, Garden & Vineyard Views
ViewHospitalityLocationCleanlinessComfortDecorOutdoor spacesIndoor spacesSleep qualityAmenitiesKitchenPoolFamilyBackyardBathroomNearbyGetting aroundAccuracyConditionBarbecueQuietLaundryCheck-inWi-FiParkingWalkabilityHot tubAccessShared spacesAir conditioningTVLayoutLong stayBreakfastCheckout
When is the best time to visit Certaldo?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $157 AUD | $133 AUD | $150 AUD | $169 AUD | $169 AUD | $181 AUD | $185 AUD | $177 AUD | $157 AUD | $167 AUD | $154 AUD | $162 AUD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Cala Violina
- Stazione Santa Maria Novella
- Spiagge Bianche
- Pisa Centrale Railway Station
- Mercato Centrale
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden





