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Holiday houses in Certaldo

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Certaldo

  • Total holiday rentals

    Explore 70 holiday rentals in Certaldo

  • Nightly prices starting at

    Certaldo holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Certaldo holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Certaldo rentals

  • 4.9 Average rating

    Certaldo stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Certaldo

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5.0 out of 5 average rating, 218 reviews

Antico Podere del 1600 nel Chianti in Toscana

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizi ed esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con stupenda vista su castello colline e vigneti con tramonti mozzafiato.

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Guest favourite
Condo in Certaldo
4.93 out of 5 average rating, 30 reviews

La casa dei colori

La casa dei colori è un delizioso appartamento nel cuore di Certaldo, a pochi metri dalla Stazione ferroviaria e 200 mt dalla funicolare che porta al borgo medievale. Nelle immediate vicinanze troviamo le famose torri di San Gimignano, a 40 km c'è Siena e sempre a 40 km c'è Firenze. E' il posto ideale per escursioni sia culturali che enogastronomiche, facilmente raggiungibile in auto oppure comodamente in treno; qui avete tutto a disposizione in un ambiente comodo, confortevole e nuovissimo.

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Guest favourite
Holiday home in San Gimignano
4.95 out of 5 average rating, 91 reviews

Tuscan House with Private Jacuzzi in Chianti

An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

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Superhost
The living area features a spacious sofa with decorative pillows and a rustic dining set. Exposed wooden beams enhance the ceiling, while terracotta tiles cover the floor. A barrel serves as a unique side table, and warm lighting creates a cozy ambiance.
Apartment in Certaldo
4.55 out of 5 average rating, 106 reviews

Tognazzi CasaVacanze - Casa il Giglio

Grazioso appartamento nel borgo medioevale di Certaldo Alto, nel cuore della Toscana. L'appartamento, a piano terra e con ingresso indipendente, dispone di cucina/soggiorno con divano letto queen size, 2 camere matrimoniali con vista panoramica e 2 bagni con doccia. A disposizione degli ospiti WI-FI, ventilatori a soffitto nelle camere da letto, riscaldamento, TV, bollitore elettrico, macchina per caffè espresso e americano, piano cottura, piccolo forno grill, tostapane, frigo e freezer.

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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.
Condo in Certaldo
4.78 out of 5 average rating, 130 reviews

In centro a Certaldo

L'appartamento si trova nel cuore di Certaldo, paese piccolo e tranquillo immerso tra le inconfondibili colline toscane, a soli 5 minuti a piedi trovate la stazione dei treni da dove potete raggiungere Siena o Firenze, e anche alte città, oppure in auto. Certaldo ha un fascino medioevale unico nel suo genere: il centro storico nella parte alta è infatti conservato splendidamente e dal nostro appartamento potrete raggiungerlo a piedi in pochi minuti oppure con una panoramica funicolare.

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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
5.0 out of 5 average rating, 230 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.

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Top Guest favourite
The historic stone facade features a large wooden door at its center, framed by a series of smaller windows with wrought iron grilles. The texture of the weathered brick is highlighted by the sunlight, creating a sense of timelessness against the clear blue sky.
Condo in Certaldo
4.98 out of 5 average rating, 95 reviews

Suite Gabri, Stiozzi Ridolfi

Suite Gabri è un appartamento all'interno di un importante palazzo nobiliare del 1300, ristrutturato nel 2007. Siamo nel magnifico borgo medievale di Certaldo Alto! Dispone di due camere matrimoniali, una camera con due letti singoli, una zona pranzo con una cucina attrezzata, un grande soggiorno, postazione per lo smart working, due bagni con doccia e lavanderia attrezzata. Parcheggio gratuito all'interno del cortile di Palazzo Stiozzi Ridolfi. Perfetta fino a 6 persone.

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Guest favourite
The image presents an aerial view of a rustic villa surrounded by rolling hills and vineyards. A rectangular swimming pool is situated in the foreground, and the greenery of the surrounding gardens enhances the serene landscape. The property showcases traditional architecture with terracotta roofs.
Apartment in San Gimignano
4.81 out of 5 average rating, 64 reviews

Il Castro Luxury San Gimignano. Michelangelo Suite

Il Castro è un gruppo di appartamenti finemente recuperati da un'attenta ristrutturazione, che ha lasciato inalterati i segni del passato. L'arredo classico, decorato in modo scrupoloso da artigiani locali, si coniuga in perfetta armonia con elementi di pregiato design, conferendo un effetto minimalista e ricercato. Straordinarie le finiture dei bagni dove la ricerca del dettaglio e la qualità dei materiali trasformano l'ambiente in qualcosa di unico nel suo genere.

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Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 105 reviews

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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Top Guest favourite
Apartment in Certaldo
5.0 out of 5 average rating, 10 reviews

Appartamento Iris - Az. Agricola Sotto il Masso

🌸 Appartamento Iris — Un sogno toscano tra colline, profumi e tramonti 🌸 Lasciati avvolgere dal fascino della Toscana autentica. L’Appartamento Iris, situato all’interno dell’Azienda Agricola “Sotto il Masso”, è un rifugio di charme immerso tra vigneti, uliveti e paesaggi che sembrano dipinti. Qui potrai ritrovare il silenzio, la bellezza e il ritmo lento della campagna toscana, senza rinunciare al comfort e all’eleganza.

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Guest favourite
Apartment in Certaldo
4.89 out of 5 average rating, 85 reviews

Center Certaldo Private Garden

You’ll love this home for its perfect location in the heart of Certaldo, just steps from the charming medieval town. Fully renovated and equipped with every comfort, it offers a cozy yet elegant atmosphere. Ideal for those who want to explore the city while enjoying relaxation, it welcomes you with stylish and functional spaces. An authentic experience that will make your stay truly unforgettable!

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Guest favourite
A private open terrace features a wooden table surrounded by several chairs. Potted plants add greenery to the space, while an umbrella stands ready for shade. The view includes trees and the sky, enhancing the outdoor dining experience.
Home in Certaldo
4.88 out of 5 average rating, 17 reviews

Casa Al Cantone

The vacation home "Casa Al Cantone" is set in the main square in Certaldo, in front of Palazzo Pretorio, and is a great accommodation for guests who are celebrating a wedding in the town. The 2-storey property consists of a living room with a sofa bed for 2 people, a fully-equipped kitchen, 1 bedroom, and 1 bathroom, and can accommodate 5 people.

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Popular amenities for Certaldo holiday rentals

When is the best time to visit Certaldo?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$171 NZD$159 NZD$162 NZD$181 NZD$194 NZD$200 NZD$206 NZD$186 NZD$183 NZD$184 NZD$166 NZD$193 NZD
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Frequently Asked Questions

  • What are the best places to stay in Certaldo?

    The historic center, Certaldo Alto, is often recommended for unique stays in restored buildings, while the lower town has more modern conveniences and transport connections. Countryside agriturismos around Certaldo invite guests to relax among vineyards and olive groves.

  • What are the best things to do in Certaldo with kids?

    Families can explore the castle-like Palazzo Pretorio, ride the funicular railway to Certaldo Alto, or join hands-on workshops held in local museums. Open-air spaces around the old town are popular for relaxed picnics and games.

  • What are some of the best things to do in Certaldo?

    Explore Certaldo Alto's medieval streets, visit the house museum of Giovanni Boccaccio, and take in views from the ancient city towers. Food lovers often enjoy traditional cooking classes or sampling local wines in cozy taverns.

  • How is the weather in Certaldo?

    Certaldo has cool winters around 36–55°F (2–13°C) and warm summers near 65–90°F (18–32°C). Rain is more frequent in autumn and winter, so a mix of layers and rain gear is helpful.

  • When is the best time to visit Certaldo?

    Late spring through early autumn is often recommended, with pleasant temperatures around 65–84°F (18–29°C) and lively cultural events. Spring wildflowers and autumn harvest celebrations bring seasonal character to the area.

  • What are the best places to visit in Certaldo?

    Explore Certaldo Alto for its medieval towers and town walls, and tour the house museum dedicated to Giovanni Boccaccio. The Palazzo Pretorio, known for its distinctive frescoes, is also frequently suggested.

  • What are some hiking trails in Certaldo?

    Certaldo has scenic walking paths that wind through vineyards, olive groves, and gentle hills around the town. The route up to Certaldo Alto and local nature trails are often suggested for panoramic countryside views.

  • What are some family activities we can do in Certaldo?

    Families often join interactive history tours, participate in cooking classes focused on local recipes, or enjoy funicular rides to Certaldo Alto. Small playgrounds and gelato shops in the historic center help keep younger travelers engaged.

  • What are some of the best day trip ideas from Certaldo?

    Many travelers explore nearby hilltowns, visit renowned vineyards in the Tuscan countryside, or experience art-rich cities like Florence and Siena. Local markets and traditional villages around Certaldo are also frequently suggested.

  • Are there any pet friendly accommodations available in Certaldo?

    Many accommodations in Certaldo welcome pets, including vacation rentals in both the town center and surrounding countryside. Parks and open spaces nearby make it easier to travel with your dog.

  • What are some local tips for visiting Certaldo?

    Wear comfortable shoes for the steep, cobbled streets in the old town and bring a camera for the panoramic views. Sampling handmade pasta at a trattoria and visiting early in the morning for a quieter atmosphere are often recommended.

  • What is Certaldo known for?

    Certaldo is known for its hilltop medieval town, association with writer Giovanni Boccaccio, and vibrant local traditions. The town’s distinctive red onions and seasonal festivals are also woven into its cultural life.

  • What are the best hidden gems to explore in Certaldo?

    Artisan workshops in the old town, quiet alleys with preserved medieval homes, and lesser-known frescoes inside small chapels are inviting to curious travelers. Early morning or late afternoon walks often reveal peaceful corners away from the main squares.

  • What are the best foods to try in Certaldo?

    Certaldo is known for its red onion, which appears in many traditional dishes, such as savory soups and stews. Other local favorites include wild boar pastas, handmade pici, and rustic Tuscan desserts.

  • What should I bring for a trip to Certaldo?

    Pack comfortable shoes for walking, a sun hat and sunglasses for summer visits, and a light jacket or umbrella if visiting in autumn or winter. A camera is great for capturing scenic views and medieval architecture.

  • What is the nightlife in Certaldo like?

    Certaldo has a relaxed nightlife centered around historic squares, small wine bars, and trattorias where guests mingle with locals. Summer evenings often bring live music and open-air events, especially in the medieval old town.

  • What are the most popular events or festivals in Certaldo?

    Certaldo hosts a well-known medieval festival in the old town during summer, with performers, markets, and lantern-lit evenings. Food and wine celebrations around the autumn harvest are also popular with visitors.

  • Are there family friendly vacation rentals in Certaldo?

    Certaldo has many family-friendly vacation rentals, especially in its quieter neighborhoods and countryside areas. Look for stays that feature kitchens, garden spaces, and easy access to the old town’s historic sites.