
Family-friendly holiday rentals in Certaldo
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Top-rated family-friendly rentals in Certaldo
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The MOONLIT & SUNNY COTTAGE near Florence
IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

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...

Apartment Montegonfoli 3 farmhouse, for 4+2 guests
Large and romantic apartment in the countryside of San Gimignano, with amazing views over the towers and hills. Can host up to 4 adults and 2 babies under 12yo. MG3 is part of Montegonfoli Farmhouse, the best place to spend a nice holiday in absolute relax, in an enchanted natural context, in the heart of Tuscany, far from the noise but at the same time very close to the most beautiful towns and attractions of the region. City center is at only 5 minutes by car. Shops and restaurants nearby.

Cottage Vittoria - Masseto In Chianti
MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Cappero (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

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.

SuiteLouise.pool, Hot Tub,homeGym & private Garden
SuiteLouise, in the chianti region is the perfect retreat for those seeking design,comfort and authentic tuscan vibes.Relax in the outdoor lounge,enjoy a bbq in the rose garden, or unwind in the private hot tub or home gym. Feel at home embraced by the rolling tuscan hills, whille i help you create tailor-made stays with 10+experiences. Contact me to craft your tuscan escape and create unforgettable memories in this strategic and amazing area between Florence and Siena.

House at Gianni - Olmo
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

House with a breathless view in Tuscany
Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

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

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.

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!!!

Medieval Village Apt btwn Florence Siena
WiFi Historical Apt with 2 Double Bedrooms, 2 Bathrooms, large Living Area and Double Sofa Bed. The apartment, completely renovated, is entirely located on the ground floor of an ancient Building in the heart of the old town of Certaldo! Free Parking
Popular amenities for Certaldo family-friendly rentals
Family-friendly home rentals with a hot tub

A Big Dream in a Little Tower.

Il Fienile, Cottage in the country with Jacuzzi

House of Delights - The Medici private leisure house

Villa di Geggiano – Guesthouse

Nada Home

Green Dome @ The Land Before Time Retreats

CasaDiManuela:TotallyPrivateChiantiVilla withTub

Barrel Suite Tuscany • Hot Tub • Vineyard View
Family- and pet-friendly home rentals

Beautiful medieval village!!!

Costalmandorlo, a rustic home in the heart of Tuscany

Casa Al Poggio & Chianti view

Historic house in heart of Tuscany

Monteriggioni Castello, holiday house in Tuscany

Countryside Cottage With View - Le Rondini apt

Florentine Hills “Le Scalette”

House in the heart of Tuscany
Family-friendly home rentals with a pool

Private pool & panoramic garden on the countryside

Infinity pool in Chianti area

Stone House with Exclusive Pool Codilungo in Chianti

Relaxation and charm in the Chianti hills

Countryside Dream farm in Tuscany

Apartment in Villa/Agriturismo with swimming pool

Borgo Ripostena – No. 8 Casa Vecchia

Trosce Lost-in-nature villa with breathtaking view
When is the best time to visit Certaldo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $192 NZD | $162 NZD | $183 NZD | $192 NZD | $193 NZD | $205 NZD | $226 NZD | $216 NZD | $192 NZD | $204 NZD | $188 NZD | $198 NZD |
| 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 |
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 $86 NZD per night before taxes and fees

Verified guest reviews
Over 1,460 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!
Destinations to explore
- Pet-friendly rentals Certaldo
- House rentals Certaldo
- Rentals with a patio Certaldo
- Villa rentals Certaldo
- Rentals with a washing machine and dryer Certaldo
- Apartment rentals Certaldo
- Rentals with outdoor seating Certaldo
- Family-friendly rentals Metropolitan City of Florence
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Mercato Centrale
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Mugello Circuit
- Piazzale Michelangelo
- Spiagge Bianche
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Parco delle Cascine
- Gulf of Baratti
- Medici Chapel
- Basilica of Santa Croce





