Search holiday homes in Certaldo from 100+ sites!

35 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Certaldo villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

35 Villa rentals in Certaldo

Browse Vacation Homes in the Historic District of Certaldo

Booking central vacation homes in Certaldo ensures seamless sightseeing, placing top-rated restaurants and downtown landmarks steps away.

Casa Al Cantone - Certaldo
9.8 17 reviews

Casa Al Cantone

house, Certaldo
This one-bedroom apartment is located in Certaldo's historic district, directly across from the Palazzo Pretorio, the town's main square. The apartment features a fully equipped kitchen, a private terrace with views of the surrounding area, and can accommodate up to 5 guests.
Casa Mili Cozy 3br With Private Garage - Certaldo
9.6 149 reviews

Casa Mili Cozy 3br With Private Garage

house, Certaldo
This apartment is in the heart of Certaldo, steps from the train station, town center, and medieval Certaldo Alta. It's been rated excellent by previous guests for its location, cleanliness, and amenities.
The apartment has 3 bedrooms and 2 bathrooms, and can accommodate up to 6 guests. It features air conditioning, Wi-Fi, a fully equipped kitchen, and a balcony with scenic views. Guests have access to all areas of the apartment, except for a storage room.
Casa Elisa - A Due Passi Dal Borgo - Certaldo
10 1 review

Casa Elisa - A Due Passi Dal Borgo

house, Certaldo
This ground-floor apartment in Certaldo offers exceptional tranquility, situated just steps from the medieval village of Certaldo Alto, the funicular, Piazza Boccaccio, and the train station, with free parking nearby. This dwelling accommodates two guests and features air conditioning, a kitchen with a fridge and freezer, and a washing machine.
Casa Al Cantone - Certaldo
9.4 16 reviews

Casa Al Cantone

house, Certaldo
Casa Al Cantone, located in Certaldo, Italy, is about 25 miles from Florence and its attractions including Piazza Matteotti, Strozzi Palace, Pitti Palace, and the Santa Maria Novella church.
This 750-square-foot (approximately 70 square meters) house rental in Certaldo boasts one bedroom, one bathroom, and sleeps up to 10 guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a terrace, parking, and is close to dining options.

Best family friendly Certaldo villas and beach houses

Among the 35 accommodations in Certaldo, here are the 4 best family friendly villas and beach houses

Podere Conte Francesco-la Palma - Certaldo
8.0 5 reviews

Podere Conte Francesco-la Palma

house, Certaldo
This three-bedroom, one-bathroom villa is located on the Podere Conte Francesco estate, seven kilometers from Certaldo, thirteen kilometers from San Gimignano, and fifty-seven kilometers from Florence, offering easy access to Tuscany's major attractions.
The 970-square-foot property features a private patio, garden, barbecue, reserved parking, and shared access to a seasonal pool (May 2nd-October 3rd); it comfortably accommodates up to six guests and includes amenities such as Wi-Fi, a microwave, and a freezer.
Villa Milani With Shared Pool, Private Terrace & Wi-fi - Certaldo
10 1 review

Villa Milani With Shared Pool, Private Terrace & Wi-fi

house, Montespertoli
This charming farmhouse is located just a short distance from Montespertoli's main attractions, including the historic Piazza Machiavelli and the bustling Piazza del Popolo, all within a 3 km radius. The surrounding area is peaceful and picturesque, offering stunning views of the Tuscan countryside.
The farmhouse is a spacious and comfortable property, ideal for families or groups of friends. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, tennis court, and a restaurant serving delicious local cuisine.
435 M² Villa ∙ 8 Bedrooms ∙ 16 Guests - Certaldo
No reviews

435 M² Villa ∙ 8 Bedrooms ∙ 16 Guests

house, Gambassi Terme
This spacious farmhouse rental is located near Gambassi Terme, a small village overlooking the hills toward Volterra, offering convenient access to Val d'Elsa and San Gimignano.
This 4680 sq ft property accommodates up to 16 guests with 8 bedrooms and 4 bathrooms, featuring a private pool, terrace, garden, air conditioning, and a ZeroDep Guarantee for peace of mind.
A Casa Di Franca Villa Con Piscina - Certaldo
9.8 19 reviews

A Casa Di Franca Villa Con Piscina

house, Gambassi Terme
A Casa di Franca Villa con piscina, a 223-square-meter (2,400-square-foot) vacation home, is located in the Chianti hills near Gambassi Terme, Tuscany, offering easy access to Tuscan attractions.
This four-bedroom, three-bathroom villa sleeps up to 14 guests and boasts a private 16-foot by 46-foot swimming pool (open May 1st to October 15th), a fully equipped kitchen, air conditioning, Wi-Fi, and free baby equipment upon request.

Frequently Asked Questions about villa rentals in Certaldo

  • What are the must-see attractions in and around Certaldo?

    Certaldo is full of charm! You'll definitely want to visit the historic center, especially the Palazzo Pretorio and the Church of San Tommaso. Take a stroll through the medieval streets and enjoy the views from the Rocca, a fortress with panoramic views of the surrounding countryside. If you're interested in art, the Museo di Arte Sacra is a must-see. For a day trip, head to the nearby town of San Gimignano, known for its iconic towers.
  • What are the best villa rentals in Certaldo?

    Among the villa rentals in Certaldo, Il Rosolaccio, Casa Badia and Country House Nazzano Près S -gimignano -Lulico are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Certaldo?

    The countryside around Certaldo is home to a variety of wildlife. You might spot hares, foxes, and wild boars in the forests. Keep an eye out for birds of prey like buzzards and kestrels soaring overhead. In the nearby Val d'Elsa, you can even see the occasional wild cat.
  • What are the best villa rentals with a pool in Certaldo?

  • What is the best time to visit Certaldo?

    Spring and fall are the best times to visit Certaldo, when the weather is mild and the crowds are smaller. You'll enjoy pleasant temperatures for exploring the town and the surrounding hills. Summer can be hot, while winter can be chilly and rainy.
  • What are the best villa rentals with a jacuzzi in Certaldo?

  • When is it easiest to book a villa rental in Certaldo?

    Booking a villa in Certaldo in the shoulder seasons, spring or fall, will give you the best rates. You'll find more availability and often better prices than during the peak summer months.
  • What are the best villa rentals for families and kids in Certaldo?

    The best villa rentals for families and kids in Certaldo are Il Rosolaccio, Casa Badia and Country House Nazzano Près S -gimignano -Lulico.

  • What are the top hiking trails near Certaldo?

    Certaldo is a great base for hiking. The Sentiero del Viandante is a popular trail that follows an old pilgrim route, offering stunning views of the Tuscan countryside. For a shorter hike, try the trail to the top of the Rocca, where you can enjoy panoramic views of the town and the surrounding hills.
  • What are the best pet friendly villa rentals in Certaldo?

    The best pet friendly villa rentals in Certaldo are Il Rosolaccio, Casa Badia and Country House Nazzano Près S -gimignano -Lulico.

  • What are the advantages of renting a house or a villa in Certaldo

    Renting a villa in Certaldo gives you more space and privacy compared to a hotel. You can enjoy a more authentic experience, cooking your own meals and relaxing in your own private space. Plus, you'll have access to amenities like a pool and garden, which are often not available in hotels.
  • What are the best villa rentals with parking in Certaldo?

    Il Rosolaccio, Casa Badia and Country House Nazzano Près S -gimignano -Lulico are the best villa rentals with parking in Certaldo.

  • Are there popular destinations near Certaldo?

    Certaldo is ideally situated for exploring Tuscany. You can easily reach the charming medieval town of San Gimignano, the historic city of Siena, and the rolling hills of Chianti. Florence, the capital of Tuscany, is also within easy reach.

Popular destinations

Best Certaldo houses with a garden

Azienda Agricola Fornacelle - Certaldo
9.6 97 reviews

Azienda Agricola Fornacelle

farm, San Gimignano
Country House Tenuta Fornacelle is located in the peaceful Tuscan countryside, just a short drive from the historic town of San Gimignano and the Certaldo Train Station. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house offers a variety of accommodations, including rooms and apartments, each with a private bathroom. Enjoy the outdoor pool, garden, and BBQ facilities, as well as free Wi-Fi, parking, and a shared lounge.
10 Appartamenti - Tennis, Pool - Chianti - Certaldo
10 1 review

10 Appartamenti - Tennis, Pool - Chianti

gîte, Montespertoli
This Montespertoli countryside rental complex, offering ten apartments sleeping up to 53 guests, provides a peaceful retreat near the town center—the exact distance requires further clarification.
Each apartment, ranging from two to three bedrooms, features amenities including a swimming pool, tennis courts, and a common outdoor area; optional services like welcome dinners and cooking classes are available.
Conte Francesco I - Certaldo
8.0 2 reviews

Conte Francesco I

house, Certaldo
This pet-friendly Tuscan villa is located on a vineyard estate near Certaldo, seven kilometers from Certaldo's center, thirteen kilometers from San Gimignano, and fifty-seven kilometers from Florence, offering a secluded countryside setting with stunning views.
This 1300-square-foot two-level home features four bedrooms, two bathrooms, and can comfortably accommodate eight guests, boasting a private terrace with a barbecue, a shared seasonal pool, and on-site parking.
L'angolo Fiorito San Gimignano Casa Indipendente - Certaldo
10 1 review

L'angolo Fiorito San Gimignano Casa Indipendente

house, San Gimignano
This independent vacation home is located close to San Gimignano's Duomo and Piazza della Cisterna, offering convenient access to these key local landmarks.
This 970 sq ft rental accommodates up to 7 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchenette, air conditioning, WiFi, a garden, and a terrace.

Best Certaldo houses with parking

Villa Montignoso - Certaldo
9.7 30 reviews

Villa Montignoso

house, Gambassi Terme
Villa Montignoso in Castagno is located 37 miles from Pisa International Airport.
This villa offers 8 bedrooms and 7 bathrooms, a private outdoor swimming pool, a garden, a fitness center, and on-site activities like table tennis and yoga classes.
Appartement à Castelfiorentino Avec Piscine - Certaldo
8.8 5 reviews

Appartement à Castelfiorentino Avec Piscine

gîte, Castelfiorentino
This apartment in Castelfiorentino offers a convenient base for exploring Tuscany, located within easy reach of the town center and surrounded by countryside.
This gîte accommodates up to 5 guests with 3 bedrooms and 1 bathroom, featuring a kitchen with a fridge and dishwasher, a garden, parking, and access to a communal swimming pool.
Agriturismo Le Ginestruzze - Certaldo
9.0 2 reviews

Agriturismo Le Ginestruzze

farm, Montespertoli
Agriturismo Le Ginestruzze is situated in Gigliola, offering a rural escape approximately 17-19 miles from Piazzale Michelangelo and Uffizi Gallery, and 18 miles from Florence Airport.
This farm stay provides air-conditioned units with a kitchen, complimentary WiFi, a year-round outdoor pool, garden, and parking, ideal for cycling enthusiasts.
Agriturismo Poggio Ai Grilli - Certaldo
9.1 34 reviews

Agriturismo Poggio Ai Grilli

farm, Gambassi Terme
Agriturismo Poggio ai Grilli is a family-friendly farm with a seasonal outdoor swimming pool and a serene garden, situated 49 km from Piazza Matteotti in Gambassi Terme. The farm has a very good user and location rating.
The farm features traditional Tuscan interiors and comfortable accommodations. Guests can enjoy amenities such as a fitness center, parking, and a 24-hour front desk.

Choose the Right Holiday Houses with Swimming Pool in Certaldo

A vacation home with a pool in Certaldo is a brilliant base for a proper swim in the heart of the city.

Apartment At First Floor In Agriturismo With Pool - Certaldo
10 80 reviews

Apartment At First Floor In Agriturismo With Pool

apartment, Certaldo
Entire Estate For 18 People At Tuscan Vineyard - Certaldo
No reviews

Entire Estate For 18 People At Tuscan Vineyard

house, Poggibonsi
800 M² Villa ∙ 8 Bedrooms ∙ 20 Guests - Certaldo
10 2 reviews

800 M² Villa ∙ 8 Bedrooms ∙ 20 Guests

house, Gambassi Terme
Tognazzi Casa Vacanze - Panoramic Villa - Villa With Private Pool And Hot Tube - Certaldo
No reviews

Tognazzi Casa Vacanze - Panoramic Villa - Villa With Private Pool And Hot Tube

house, Certaldo

Best Luxury Vacation Homes in Certaldo

For those who appreciate quality, these high-end vacation homes in Certaldo deliver premium comfort on every front.

Casa Natura - Certaldo
9.5 62 reviews

Casa Natura

house, San Gimignano

Check Out Vacation Homes with a Hot Tub in Certaldo

These vacation homes in Certaldo feature private hot tubs, perfect for a secluded soak after a day of urban exploration.

Appartamento Maria - Certaldo
9.7 12 reviews

Appartamento Maria

farm, San Gimignano
Tognazzi Casa Vacanze - Dimora Bunny E Danny - Certaldo
9.0 3 reviews

Tognazzi Casa Vacanze - Dimora Bunny E Danny

house, San Gimignano
Villa Simone By Posarellivillas - Certaldo
9.7 49 reviews

Villa Simone By Posarellivillas

house, San Gimignano
Tenuta Di Sticciano - Certaldo
8.6 225 reviews

Tenuta Di Sticciano

farm, Certaldo
©2026 cozycozy.com