Certaldo holiday lettings

We found 1,463 holiday rentals — enter your dates for availability

Discover a selection of 9 homes and other holiday rentals in Certaldo that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you need and want for your stay, which might include a garden and hot tub. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Why visit Certaldo

  • Rich cultural heritage: Discover charming churches, intriguing museums, and lively piazzas that reflect the essence of Italian culture.
  • Stunning landscapes: Explore the nearby Chianti Hills, offering breathtaking views and picturesque scenery.
  • Romantic atmosphere: Certaldo provides a relaxing environment, perfect for couples seeking a romantic getaway.
  • Charming accommodations: Choose from a variety of delightful holiday rentals, including cosy apartments and luxurious villas.
  • Excursions to historic towns: Venture to nearby towns for a taste of luxury and seclusion amidst rich history.

Popular types of accommodation in Certaldo

Vrbo offers a fantastic selection of holiday rentals in Certaldo, perfect for British travellers seeking comfort and charm. Whether you prefer a cosy apartment, a private vacation home, or a luxurious villa, you’ll find the ideal accommodation to suit your needs. Our guests often opt for Certaldo villa rentals, which provide ample space and stunning views. Explore the delightful options and make your stay in this picturesque town truly memorable.

  • Apartments: The top choice for visitors in Certaldo, offering modern amenities and a home-like atmosphere for a comfortable stay.
  • Houses: Ideal for families or groups, these homes provide a spacious and personalised experience.
  • Villas: Luxurious and often set in picturesque surroundings, perfect for those seeking elegance and relaxation.
  • Caravan Parks: A unique option for adventurous souls, combining nature with a sense of community.
  • Cottages: Quaint and charming, these are perfect for a cosy retreat in the heart of Tuscany.**

Top attractions in and around Certaldo

Certaldo, nestled in Tuscany, is perfect for a romantic and culturally enriching getaway. Visitors can explore charming churches, intriguing museums, and lively piazzas, all catering to those seeking a rich cultural experience. Additionally, the nearby Chianti Hills offer stunning landscapes, ideal for a coastal getaway. Whether you're travelling as a couple or solo, Certaldo promises a delightful blend of entertainment and cultural immersion.

  • San Gimignano Communal Palace: This historic civic government building, located 3.7km from Certaldo, showcases stunning medieval architecture and rich cultural heritage. Visitors can explore its impressive halls and learn about the town's history.
  • Piazza della Cisterna: A charming square, also 3.7km from Certaldo, surrounded by beautiful towers and medieval buildings. It’s the perfect spot to soak in the vibrant atmosphere, enjoy local cuisine, and admire the city’s culture.
  • Casa del Boccaccio: Situated within Certaldo, this historic house is the birthplace of the famous writer Giovanni Boccaccio. The museum offers insights into his life and works, making it a must-visit for literature enthusiasts.

Things to do recommended for couples

For a romantic getaway in Certaldo, visit the enchanting Tenuta Torciano Winery, just 1.9km away, or the charming Tenuta Maiano, located 3.1km away, both offering delightful outdoor experiences. Don’t miss the stunning Antinori nel Chianti Classico, a mere 5.6km from your base.

Things to do recommended for families

Your family vacation in Certaldo will be delightful, with a visit to the Stadio Carlo Castellani for a spirited sports atmosphere, the Chianti Observatory for exciting planetarium shows, and the Nelson Mandela Forum for wellness and relaxation, all within a short drive of your base.

Things to do recommended for groups

Groups visiting Certaldo can enjoy a round of golf at Castelfalfi Golf Course, immerse themselves in culture at Teatro del Silenzio, and unwind with drinks at Il Fiaschetto for a lively evening. These activities offer a delightful blend of sports, entertainment, and romance.

What do I need to keep in mind when booking a vacation in 'Certaldo

If you’re travelling with a group, family, pets, or seeking extended stays, be sure to use the appropriate filters to prioritise your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Certaldo with a group: Think about how many bedrooms you require, along with features such as a fully equipped kitchen or outdoor areas for gatherings. Fortunately, you can easily refine your search for all these options, and many more, on Vrbo.
  • Traveling to Certaldo with young kids: Traveling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it would be wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Certaldo: For many, a family holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Certaldo: If you're in search of holiday rentals that offer savings for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Certaldo

Certaldo, nestled in the heart of Tuscany, offers a delightful blend of romance, culture, and entertainment. Explore beautiful villas and estates that capture the essence of Italian charm. With its relaxing atmosphere and friendly locals, you'll find Certaldo a perfect base for memorable excursions. Don’t miss the chance to visit nearby historic towns, where luxury and seclusion await, ensuring a truly enchanting holiday experience in this picturesque region.

  • Certaldo Alto: Nestled atop a hill, Certaldo Alto is a charming medieval neighbourhood that offers a captivating blend of history and culture. Visitors are drawn to its cobbled streets, picturesque views, and romantic atmosphere. Explore the historic houses and museums that showcase the rich heritage of the region. The local shopping centre and bustling theatre provide lively entertainment options, making it an ideal spot for both relaxation and exploration. Don't miss the stunning views of the surrounding Tuscan landscape that can be enjoyed from the ancient walls.
  • Marcialla: A quaint village near Certaldo, Marcialla is perfect for those seeking a romantic escape intertwined with entertainment. The village's inviting piazza square is a focal point for visitors, often hosting local events and gatherings. With its historic palace and charming streets, Marcialla offers a delightful backdrop for leisurely strolls. Theatre performances and guided tours of the area allow tourists to immerse themselves in the local culture and history, making it an enriching experience for all.
  • San Donnino: This delightful village is ideal for families and urban explorers alike. San Donnino boasts a mix of outdoor experiences and urban charm, with its lovely urban park providing ample space for picnics and play. The area is rich in historic sites, allowing visitors to delve into the past while enjoying the natural beauty surrounding them. With its welcoming atmosphere and accessible amenities, San Donnino serves as a fantastic base for exploring the broader Certaldo region.

Best time to go to Certaldo

If you're planning a trip to Certaldo, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
February43.3°F (6.3°C)Light RainMostly SunnyAverageSlightly Low
March48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
April54.9°F (12.7°C)Light RainMostly SunnySlightly HighAverage
May61.5°F (16.4°C)Light RainMostly SunnySlightly HighAverage
June70.7°F (21.5°C)Light RainSunnyAverageSlightly High
July76.3°F (24.6°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.9°F (24.4°C)No Rain (Dry)SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
November50.4°F (10.2°C)Light RainMostly SunnySlightly LowSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as this can significantly impact prices. Furthermore, opting for a longer stay often results in substantial savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area for you to create new trips, manage your plans, or review and organise your bookings. The properties you’ve saved or booked are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Relaxing Certaldo will entice you

The area's history and festivals are just some of the reasons to come on holiday to Certaldo. Travellers appreciate the gardens in this relaxing city. Piazza di Santa Maria Novella and Cathedral of Santa Maria del Fiore are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Certaldo

Do you want to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Certaldo a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Tenuta Torciano Winery (3.3 mi / 5.3 km)
  • Sovestro in Poggio Winery (6.1 mi / 9.9 km)
  • Castello di Monsanto (8.3 mi / 13.3 km)
  • Antinori nel Chianti Classico (8.7 mi / 14.1 km)
  • Castelfalfi Golf Course (9.3 mi / 14.9 km)
  • Casa Sola - Chianti Winery (9.4 mi / 15.2 km)

Exploring the natural features in Certaldo

Travellers enjoy Certaldo for its gardens and countryside. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Certaldo. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Boboli Gardens (18.1 mi / 29.2 km)
  • Cascine Park (18.5 mi / 29.8 km)
  • Arno River (18.6 mi / 29.9 km)
  • Sentierelsa Trail (9.7 mi / 15.6 km)
  • Alta Val d'Elsa River Park (11.9 mi / 19.2 km)
  • Hedonistic Hiking (15.2 mi / 24.5 km)

Transport to and around Certaldo

The nearest airport is in Peretola Airport (FLR), located 19.3 mi (31.1 km) from the city centre.

If you prefer train travel, the main station is Certaldo Station.

Frequently asked questions

What is the best area to stay in Certaldo when booking a holiday rental?
When considering a holiday rental in Certaldo, Tuscany, the best area to stay is the historic centre, often referred to as Certaldo Alto. This charming hilltop village offers a unique blend of medieval architecture and stunning views of the surrounding Tuscan countryside. The cobbled streets are lined with quaint shops, local eateries, and beautiful squares, making it an ideal spot for immersing yourself in the local culture.

One of the top attractions in Certaldo Alto is the Palazzo Pretorio, a striking medieval palace that showcases a fascinating collection of artworks and historical artifacts. The area is also famous for its annual Boccaccesca food festival, celebrating local cuisine and wines, which can be a delightful experience for food enthusiasts.

In terms of holiday rentals, this area features a variety of properties, from charming apartments in restored buildings to cosy villas, suiting different tastes and budgets.
How much does it cost to rent a holiday home in Certaldo?
Prices for holiday rentals in Certaldo vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Certaldo to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Certaldo holiday house rentals?
You can find great discounts on house rentals in Certaldo on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Certaldo?
In Certaldo, apartments are the most popular type of holiday rental, with approximately 292 available throughout the area. These apartments are often situated in charming neighbourhoods, providing guests with easy access to local attractions such as the historic Certaldo Alto and the beautiful Tuscan countryside. Most apartments come equipped with fully fitted kitchens, comfortable living areas, and some may even feature balconies or terraces for enjoying the stunning views.

In addition to apartments, there are about 168 villas and 128 holiday houses available for those seeking more space and privacy. These properties typically offer multiple bedrooms, spacious gardens, and outdoor dining areas, making them ideal for families or larger groups looking to relax and soak in the serene Tuscan landscape.
Are there any family house rentals in Certaldo?
In Certaldo, Tuscany, there are numerous family-friendly house rentals available, with around 77 options to choose from. This picturesque town offers a blend of history and natural beauty, making it an ideal destination for families looking to explore the region. Many of these properties come with spacious living areas, fully equipped kitchens superb for family meals, and outdoor spaces where children can play and enjoy the Tuscan sun.

Visitors will find that amenities such as Wi-Fi and air conditioning are commonly included, ensuring a comfortable stay. Certaldo is well-known for its medieval architecture, and families can easily visit nearby attractions like the charming Certaldo Alto, which is accessible by a funicular railway, or explore the beautiful vineyards in the surrounding countryside.
Can I rent a holiday home with a pool or hot tub in Certaldo?
In Certaldo, Tuscany, there are approximately 110 holiday homes available for rent that feature pools or hot tubs, making it an excellent choice for travellers seeking relaxation and leisure. This picturesque town, known for its medieval architecture and scenic landscapes, offers a variety of neighbourhoods where these properties can be found, including the charming historic centre and the surrounding countryside.

Visitors can expect a range of amenities in these rentals, such as private swimming pools, outdoor hot tubs, and spacious gardens great for enjoying the stunning Tuscan sun. Many properties also include fully equipped kitchens, allowing guests to prepare local delicacies, and comfortable living areas for unwinding after a day of exploration.
Can I find long-stay holiday rentals in Certaldo?
A long-stay holiday rental in Certaldo is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Certaldo?
In Certaldo, Tuscany, there are numerous pet-friendly house rentals available, providing ample options for travellers looking to enjoy this picturesque region with their furry companions. Many of these holiday homes come equipped with amenities such as spacious gardens, private patios, and fully equipped kitchens, allowing for comfortable stays.

The charming town itself is known for its medieval architecture and beautiful landscapes, making it a delightful backdrop for a holiday. Some rentals are situated close to local parks and open spaces, offering opportunities for walks and outdoor adventures with pets. Additionally, the surrounding area is dotted with vineyards and scenic countryside, superb for exploring with your four-legged friends.
Are there any remote work holiday rentals in Certaldo?
In Certaldo, Tuscany, there are a significant number of remote work holiday rentals available, with around 532 options to choose from. This charming town, known for its medieval architecture and picturesque landscapes, offers a variety of accommodations that cater to remote workers' needs. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces including desks and chairs, and comfortable living areas conducive to productivity.

Staying in Certaldo allows you to immerse yourself in the stunning Tuscan countryside while enjoying the convenience of local cafes and restaurants that serve traditional Italian cuisine. The town also features cultural highlights like the historic Palazzo Pretorio and the beautiful views from the nearby hilltop village of Certaldo Alto. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Certaldo holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Certaldo with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Certaldo?
In Certaldo, popular rental amenities include well-equipped kitchens, which allow guests to prepare meals using fresh local ingredients. Many properties also offer onsite parking, making it convenient for those travelling by car. Additionally, several rentals are pet-friendly, welcoming furry companions, and accommodating service animals. Outdoor spaces such as decks or patios are common, providing a lovely area for guests to enjoy the Tuscan countryside views.
When is the best time to visit Certaldo for a holiday rental?
April is the most popular time to visit Certaldo, as it falls within the peak season from March to May. During this period, the charming Tuscan town comes alive, attracting visitors eager to explore its rich history, stunning landscapes, and delightful cuisine. The mild spring weather, with temperatures typically ranging from 10 to 20 degrees Celsius, creates ideal conditions for outdoor activities and leisurely sightseeing.

As you wander through Certaldo's medieval streets, you'll discover captivating sights like the Palazzo Pretorio and the iconic Certaldo Alto, all while enjoying the vibrant setting that spring brings. The blooming flowers and lush greenery enhance the town's picturesque charm, making it a superb backdrop for memorable photographs.

For those looking for a more budget-friendly option, consider visiting in November. This month allows you to experience the tranquil beauty of Certaldo without the crowds, offering a unique opportunity to immerse yourself in the local culture and enjoy the stunning autumn scenery. You'll find that many local eateries and shops are still open, allowing you to savour the authentic Tuscan experience at a more leisurely pace.

Ultimately, the best time to book a holiday rental in Certaldo depends on your preferences—whether you're drawn to the bustling energy of spring or the serene charm of autumn.
How early should I book a Certaldo holiday rental?
Book your Certaldo holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Certaldo?
In Certaldo, visitors can engage in the rich history and culture of this charming Tuscan town. The historic centre, Certaldo Alto, is a must-visit, featuring narrow cobblestone streets and stunning medieval architecture. The Palazzo Pretorio, with its impressive façade and artwork, offers insight into the town's past.

Another highlight is the Church of Saint Jacob and Saint Philip, which houses beautiful frescoes and is a testament to the town's artistic heritage. For those interested in literature, the house of Giovanni Boccaccio, the famous poet and writer, is located here and offers a glimpse into his life and works.

The surrounding countryside is equally captivating, with scenic vineyards and olive groves that invite exploration. Visitors can also enjoy local festivals, particularly the Certaldo Fair, which celebrates the town's cultural traditions.
Can I change or cancel my Certaldo home rental booking on Vrbo?
To find Certaldo holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Certaldo holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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