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Holiday rentals 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 €44 per night before taxes and fees

  • Verified guest reviews

    Over 1,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Certaldo holiday rentals include wifi 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 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
5 out of 5 average rating, 340 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to you. 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 swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique sunsets.

Top guest favourite
Townhouse
4.89 out of 5 average rating, 332 reviews

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

Guest favourite
Apartment
4.96 out of 5 average rating, 26 reviews

The House of Colors

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.

Guest favourite
Holiday home
4.94 out of 5 average rating, 82 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

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
5 out of 5 average rating, 223 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
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay
4.92 out of 5 average rating, 274 reviews

Casa al Gianni - Hut

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!

Guest favourite
Castle
5 out of 5 average rating, 24 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Top guest favourite
Home
5 out of 5 average rating, 75 reviews

Relax in Tuscany Country Home with a Stunning View

An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an stunning view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a peaceful and relaxing holiday.

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
4.78 out of 5 average rating, 127 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 spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home
4.99 out of 5 average rating, 311 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Guest favourite
Flat
4.9 out of 5 average rating, 79 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!

Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower
4.95 out of 5 average rating, 214 reviews

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.

Popular amenities for Certaldo holiday rentals

When is the best time to visit Certaldo?

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Avg. price€88€82€84€97€82€94€107€96€94€95€86€100
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.