Some info has been automatically translated. Show original language

Holiday rentals in Certaldo

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Certaldo

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

1 of 1 pages1 / 1
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, 338 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.

Guest favourite
Apartment
4.96 out of 5 average rating, 25 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.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 235 reviews

Sunset on Chianti Classico

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favourite
The image features a rustic stone house surrounded by lush greenery, with a wooden door and shuttered windows. A set of stairs leads to a raised outdoor area, partially enclosed by a stone wall, providing a serene view of the surrounding nature.
Holiday home
4.94 out of 5 average rating, 80 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, 220 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 spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment
5 out of 5 average rating, 52 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favourite
Home
5 out of 5 average rating, 73 reviews

Relaxing Country Home in Tuscany with View

An incredible experience between flavor, nature 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 amazing view. A countryside Tuscan home, surrounded by olive’s fields and greenery, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful 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, 126 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.

Guest favourite
Home
5 out of 5 average rating, 7 reviews

Open Space Piscina e Giardino

La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.

Guest favourite
Flat
4.9 out of 5 average rating, 77 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, 213 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.

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
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.

Popular amenities for Certaldo holiday rentals

When is the best time to visit Certaldo?

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

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!