
Vacation rentals in Certaldo
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Quick stats about vacation rentals in Certaldo

Total vacation rentals
Explore 70 vacation rentals in Certaldo

Nightly prices starting at
Certaldo vacation rentals start at G$10,463 GYD per night before taxes and fees

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Over 2,050 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Certaldo vacation 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 vacation rentals in Certaldo
Guests agree: these stays are highly rated for location, cleanliness, and more.

Podere Vergianoni immerso nelChianti con piscina
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.

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

Cosy Tuscan Home near Florence & San Gimignano
UN NIDO ACCOGLIENTE dove tradizione e confort moderno s'incontrano. Perfetto per chi desidera rallentare, rilassarsi e vivere la Toscana più autentica, lontano dal caos. Immagina di svegliarti nel cuore di un borgo toscano, affacciarti sulla piazza e iniziare la giornata con la tranquillità e I ritmi locali. L'appartamento completamente ristrutturato e arredato con gusto, si trova nel centro storico di Gambassi Terme, un punto strategico per eslorare le meraviglie della Toscana.

Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

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.

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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

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.

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.

Lorenzo Charme in Chianti
This unique space has a style all its own. With attention to detail, it has all the features to promote a holiday in Charm and luxury. Suitable for everyone and equipped with every comfort. It is centrally located, suitable for visiting all the most interesting places; Florence is only 30 km away and Siena is 35 km away.

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!!!
Popular amenities for Certaldo vacation rentals
Other great vacation rentals in Certaldo

AnticaVista, Luxury Apartment with Tower Views

The House of Colors

Casa La Selva

house with terrace overlooking tuscan countryside

Luxury Medieval Tower • Exclusive Chianti Stay

Authentic Tuscany Experience in our Country House

Herons Superior Apartment - Splendid view!

Iris Apartment - Az. Agricola Sotto il Masso
When is the best time to visit Certaldo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,135 GYD | G$19,670 GYD | G$20,089 GYD | G$22,391 GYD | G$24,065 GYD | G$24,692 GYD | G$25,529 GYD | G$23,018 GYD | G$22,600 GYD | G$22,809 GYD | G$20,507 GYD | G$23,855 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 |
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.
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
- Spiagge Bianche
- Pisa Centrale Railway Station
- Mercato Centrale
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden





