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Certaldo vacation rentals

Vacation rentals in Certaldo by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.

Certaldo is best known for its connection to the Renaissance writer Giovanni Boccaccio, with landmarks like Boccaccio's House and the medieval Certaldo Alto offering rich historical insights. Visitors attend the Mercantia festival, explore the charming streets lined with traditional Tuscan eateries, and enjoy the picturesque views of the rolling hills. Houfy connects you directly with local hosts in Certaldo, ensuring you book with local hosts. Choose from countryside villas, rustic farmhouses, and charming town apartments, with easy access to nearby towns like San Gimignano and Volterra. The fall grape harvest season provides an authentic Tuscan experience.

Recommended Homes in Certaldo

Handpicked properties we think you'll love in Certaldo.

Il Sorriso

2 bd·2 ba

€529.00 EUR total for 5 nights

Apr 18 – 23, 2027

Podere La Torre

1 bd·1 ba

€453.00 EUR total for 4 nights

Oct 14 – 18, 2026

Il Vallone

2 bd·2 ba

€462.00 EUR total for 3 nights

Apr 18 – 21, 2027

Podere La Torre

2 bd·1 ba

€503.00 EUR total for 4 nights

Oct 14 – 18, 2026

Podere La Torre

1 bd·1 ba

€453.00 EUR total for 4 nights

Oct 14 – 18, 2026

Why visit Certaldo

Discover what makes Certaldo a perfect vacation rental destination.

Medieval Charm

Visit the ancient walled town of Certaldo Alto.

Take the funicular from the modern town to Certaldo Alto and explore its medieval architecture, just a 5-minute ride away.

Taste Local Wines

Experience wine tasting at nearby vineyards.

Enjoy a tour and tasting at Tenuta Torciano, located 15 minutes from the city center, featuring classic Tuscan wines.

Boccaccio's Birthplace

Visit the house of writer Giovanni Boccaccio.

Explore the Museo Casa di Boccaccio, dedicated to the renowned writer, just a short walk in Certaldo Alto.

September Medieval Festival

Attend the annual Mercantia festival in July.

Experience street performances and craft markets during Certaldo's Mercantia festival, held each July within the historic walls.

Where to stay in Certaldo

The best areas and neighborhoods for your vacation rental in Certaldo.

Certaldo Alto

This historic area is the heart of medieval Certaldo. Cobbled streets and panoramic views make it ideal for history lovers.

Best for: history buffs, architecture enthusiasts

Certaldo Basso

Modern Certaldo offers amenities and services, including shops and the railway station, perfect for day-trip planners.

Best for: families, practical travelers

Fiano

A charming hamlet offering a peaceful retreat among vineyards, ideal for those wanting rural Tuscany's tranquility.

Best for: nature lovers, relaxation seekers

Sciano

This small village features stunning landscapes and is close to hiking trails, attracting outdoor enthusiasts.

Best for: hikers, adventure seekers

Certaldo vacation rentals with free WiFi or air conditioning

Free WiFi, air conditioning and more — every Certaldo vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Certaldo

All within driving distance of Certaldo vacation rentals.

Palazzo Pretorio

The 12th-century palace is notable for its distinctive brick facade and coats of arms. · 0.3 miles

Museo di Arte Sacra

Displays sacred art and artifacts from local churches, housed in a medieval convent. · 0.4 miles

Parco Collinare di Canonica

A beautiful park offering panoramic views of the Tuscan hills, perfect for picnics. · 1 mile

Teatro dei Leggieri

This compact theater hosts a variety of performances in an intimate setting. · 0.3 miles

La Sosta di Boccaccio

Enjoy traditional Tuscan cuisine at this well-loved local restaurant. · 0.2 miles

Sagra Della Bistecca

A festival celebrating Tuscan steak, featuring local vendors and live music. · 0.5 miles

Getting to and around Certaldo

Certaldo can be reached by train, car, or nearby airports offering convenient travel options.

Train
CERTALDO TRAIN STATION
Located in the town center, it offers regular services to Florence and Siena.
Driving
CAR RENTAL
Rental services available at Florence and Pisa airports; explore Tuscany at your own pace.
Airports
FLORENCE AIRPORT
35 miles from Certaldo, offering domestic and international flights.
PISA AIRPORT
45 miles away, providing wider flight options and car rentals.

Similar vacation rentals near Certaldo

Homes within 60 miles of Certaldo, from verified hosts.

Villa dei 2 Ulivi (Abbadia Isola)

6 bd·4 ba
5· 238

€1,604.00 EUR total for 3 nights

Oct 14 – 17, 2026

Al Soffio del Sole | Marina Apartment

1 bd·1 ba
4.82· 11

€418.35 EUR total for 3 nights

Oct 14 – 17, 2026

La Chiave di Sol

1 bd·1 ba
4.88· 43

€363.50 EUR total for 3 nights

Oct 20 – 23, 2026

Al Soffio del Sole | Amalfi Apartment

1 bd·1 ba
5· 15

€350.40 EUR total for 3 nights

Oct 14 – 17, 2026

Casa Ettore - Historic Palazzo

3 bd·3 ba
5· 19

$1,258.00 USD total for 3 nights

Oct 23 – 26, 2026

Bettini House – House with terrace near Florence

2 bd·1 ba
5· 5

€360.00 EUR €306.00 EUR total for 3 nights

Oct 24 – 27, 2026

La Chiave di Sol 2

2 bd·1 ba
5· 21

€443.50 EUR total for 3 nights

Oct 14 – 17, 2026

€558.00 EUR €510.60 EUR total for 3 nights

Jun 1 – 4, 2027

€180.00 EUR €162.00 EUR total for 3 nights

Oct 18 – 21, 2026

Casina di Andrea with an above-ground pool

2 bd·2 ba
5· 12

€680.00 EUR total for 3 nights

Jan 2 – 5, 2027

$355.00 USD total for 7 nights

Oct 14 – 21, 2026

Premium - Orange

1 bd·1 ba
4.5· 2

€557.50 EUR total for 5 nights

Oct 14 – 19, 2026

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