
Family-friendly vacation rentals in Certaldo
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Certaldo

Total vacation rentals
Explore 30 vacation rentals in Certaldo

Nightly prices starting at
Certaldo vacation rentals start at G$10,457 GYD per night before taxes and fees

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Certaldo vacation 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 - Hut
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility 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 incomparable sunsets.
KitchenIndoor spacesHospitality

Cosy Tuscan Home near Florence & San Gimignano
A COZY NEST where tradition and modern comfort meet. 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 the day in harmony with the local tranquility and rhythms. The apartment, completely renovated and tastefully furnished, is located in the historic center of Gambassi Terme, a strategic location for exploring the wonders of Tuscany.
FamilyIndoor spacesParking

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
KitchenIndoor spacesHiking

Giglio Blu Charming Loft + Air Conditioning
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...
KitchenIndoor spacesLocation

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.
KitchenFamilyAir conditioning

Il Castello di Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.
KitchenIndoor spacesWifi

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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Nada Home
In my home, you can experience the most authentic side of Tuscany, filled with peace, warmth and family traditions. Surrounded by olive groves and vineyards in the heart of Chianti, you will have a private garden all to yourself, where you can relax in complete tranquillity. On request, you can join a cooking class in the house, preparing our family recipes handed down by Grandma Graziella, or share a special dinner in an intimate and welcoming atmosphere.
FamilyKitchenWalkability

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.
KitchenFamilyHospitality

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.
Indoor spacesFamilyCleanliness

Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
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Popular amenities for Certaldo family-friendly rentals
Family-friendly home rentals with a hot tub

Typical Tuscan country house
KitchenIndoor spacesQuiet

Villa di Geggiano - Guesthouse
KitchenIndoor spacesCheck-in

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
FamilyKitchenCleanliness

SuiteLouise.pool, Hot Tub,homeGym & private Garden
Indoor spacesFamilyPool

CasaDiManuela:TotallyPrivateChiantiVilla withTub
FamilyKitchenLocation

La Cipressina Relax in Tuscany
Indoor spacesFamilyHeating

Il Fienile, Cottage in the country with Jacuzzi
KitchenFamilyAir conditioning

Torretta Apartment
KitchenFamilyBreakfast
Family- and pet-friendly home rentals

Historic house in heart of Tuscany
KitchenIndoor spacesAccuracy

Paluffo Stillo House
FamilyKitchenLaundry

Small renovated barn
KitchenFamilyWalkability

Florentine Hills "Le Scalette"
KitchenIndoor spacesGrill

Beautiful medieval village!!!
KitchenFamilyQuiet

TREEhouse/casaBARTHEL
FamilyIndoor spacesBathroom

Luxury Villa in the very heart of Chianti
Indoor spacesFamilyBackyard

Authentic among stones and bricks
FamilyKitchenWalkability
Family-friendly home rentals with a pool

Stone House with Exclusive Pool Codilungo in Chianti
KitchenIndoor spacesLong stay

App.with pool and beautiful view, 5 adults
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Infinity pool in Chianti 1
FamilyKitchenHospitality

Relaxation and charm in the Chianti hills
Indoor spacesFamilyCheck-in

Comfort Apartment in the Chianti Vineyards
FamilyIndoor spacesCheck-in

Cottage Cappero - Masseto In Chianti
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Tenuta di Pomine Certaldo (Fi) Edera Apartment
FamilyKitchenCleanliness

Torre dei Belforti
KitchenIndoor spacesGrill
When is the best time to visit Certaldo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$23,214 GYD | G$19,659 GYD | G$22,168 GYD | G$25,096 GYD | G$25,096 GYD | G$26,769 GYD | G$27,397 GYD | G$26,142 GYD | G$23,214 GYD | G$24,678 GYD | G$22,796 GYD | G$24,050 GYD |
| 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
- Mercato Centrale
- Uffizi Gallery
- Pisa Centrale Railway Station
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Gulf of Baratti
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria





