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Holiday rentals in Certaldo

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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
A shaded gazebo area is surrounded by lush greenery, featuring comfortable seating arranged on stone flooring. Soft lighting illuminates the space, creating a relaxing ambiance. Steps lead down from the gazebo to a tranquil swimming pool, reflecting the evening sky.
Apartment
5 out of 5 average rating, 334 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favourite
Home
5 out of 5 average rating, 269 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

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, 234 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
Flat
4.97 out of 5 average rating, 280 reviews

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

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, 217 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
The exterior of a rustic farmhouse is highlighted, featuring warm-colored walls and a traditional tiled roof. A large tree stands prominently, while outdoor seating is arranged on the grassy area, offering a serene atmosphere surrounded by lush greenery and a partially cloudy sky.
Farm stay
4.94 out of 5 average rating, 179 reviews

House at Gianni - Olmo

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!

Top guest favourite
Home
4.99 out of 5 average rating, 141 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Guest favourite
Apartment
4.78 out of 5 average rating, 125 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
An expansive terrace showcases a dining table set for six, complemented by comfortable seating. A shaded canopy provides relief from the sun, while surrounding greenery enhances the atmosphere. Panoramic views of Florence are visible in the background, underscoring an inviting outdoor space.
Apartment
5 out of 5 average rating, 112 reviews

Exclusive Florence Penthouse with city views

The truly Florentine soul of this exquisite apartment and its panoramic terrace sets the stage for an unforgettable stay. From this privileged vantage point above the rooftops, you can almost touch Florence’s monuments as you sip a sunset aperitivo, or greet the morning beneath the pergola with a leisurely breakfast while the city awakens in golden light.

Top guest favourite
A charming balcony is featured, adorned with colorful flowers and greenery along the wall. A small wooden table and two foldable chairs are positioned against the wall, while a planter brimming with pink flowers sits nearby, creating a pleasant outdoor space.
Flat
4.98 out of 5 average rating, 129 reviews

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!!!

Superhost
A spacious living area features a light-colored sofa and a dining table set for four. Bright overhead lights and a chandelier illuminate the space. Modern kitchen appliances are visible, along with decorative wall mirrors that enhance the light and openness of the room.
Flat
4.81 out of 5 average rating, 220 reviews

Medieval Village Apt btwn Florence Siena

WiFi Historical Apt with 2 Double Bedrooms, 2 Bathrooms, large Living Area and Double Sofa Bed. The apartment, completely renovated, is entirely located on the ground floor of an ancient Building in the heart of the old town of Certaldo! Free Parking

Top guest favourite
Cottage
4.93 out of 5 average rating, 277 reviews

Lovely countryhouse on Chiant hills

Lovely view on the valley, sweet relax in the smelling garden under a very old tree tasting a good wine and then to visit Firenze, Pisa, Siena only 30 km far from here and medieval castles,little churchs ,winery,across the beautiful Chianti road.....

Popular amenities for Certaldo holiday rentals

When is the best time to visit Certaldo?

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Avg. price€88€81€83€96€81€93€106€95€94€94€85€99
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Certaldo?

    Experience the best of Certaldo with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Certaldo?

    Yes! Work meets play with ease at over 30 vacation rentals in Certaldo featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Certaldo?

    Four-legged friends are welcome in Certaldo. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Certaldo have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Certaldo. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Certaldo have a kitchen?

    Absolutely! We offer over 10 condo rentals with a kitchen in Certaldo. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Certaldo have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Certaldo. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Certaldo have free parking?

    Absolutely! We offer over 10 condo rentals with free parking in Certaldo. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Certaldo?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with air conditioning, over 40 homes with a kitchen, over 10 homes with free parking, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 €43 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!