
Holiday houses in Certaldo
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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 $88 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

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

La casa dei colori
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.

Tramonto sul 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.

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

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

In centro a Certaldo
L'appartamento si trova nel cuore di Certaldo, paese piccolo e tranquillo immerso tra le inconfondibili colline toscane, a soli 5 minuti a piedi trovate la stazione dei treni da dove potete raggiungere Siena o Firenze, e anche alte città, oppure in auto. Certaldo ha un fascino medioevale unico nel suo genere: il centro storico nella parte alta è infatti conservato splendidamente e dal nostro appartamento potrete raggiungerlo a piedi in pochi minuti oppure con una panoramica funicolare.

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.

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.”

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.

To be happy in Tuscany with comfort & view!
Un rifugio tra gusto, natura e relax nel cuore del Chianti. Una posizione strategica tra Barberino Tavarnelle, San Gimignano, Greve in Chianti e Firenze. Belvedere 27/A si affaccia sul Castello di Santa Maria Novella, tra vigne, oliveti e una vista che toglie il fiato. Un appartamento indipendente, immerso nel verde e dotato di ogni comfort per un soggiorno all’insegna della pace e del benessere.

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!

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.

Casa in torre medioevale con vista a Certaldo
Casa vacanze situata nel cuore del borgo medioevale di Certaldo. Appartamento al secondo piano senza ascensore costituito da cucina con sala da pranzo, camera con TV al plasma e terrazza, bagno con cabina doccia, cameretta con divano letto, zona relax e vista panoramica. Ampio giardino con barbecue! Posti letto complessivi 4. Free WiFi!!!
Popular amenities for Certaldo holiday rentals
Other great holiday rentals in Certaldo

Da Francesco in Certaldo Alto

Luxury Medieval Tower - Penthouse

Villa la scuderia quiet luxury private garden pool

Farmholiday Villino del Grillo in San Gimignano SI

Capanna Frui Ruris, San Gimignano

Tognazzi CasaVacanze - Casa il Giglio

TOWER HOUSE TUSCANY - CASA TORRE

Herons Superior Apartment - Splendid view!
When is the best time to visit Certaldo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $177 NZD | $165 NZD | $168 NZD | $195 NZD | $165 NZD | $188 NZD | $214 NZD | $193 NZD | $189 NZD | $191 NZD | $172 NZD | $200 NZD |
| 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
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Spiagge Bianche
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Gulf of Baratti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria





