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Certaldo villas
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35 Villa rentals in Certaldo

Holiday Homes with a Pool in Certaldo

Spend your days relaxing poolside in absolute privacy right in your backyard at houses with a pool in Certaldo.

Conte Francesco I - Certaldo
8.0 2 reviews

Conte Francesco I

house, Certaldo
This four-bedroom house, situated on a vineyard estate 7km from Certaldo, 13km from San Gimignano, and 57km from Florence, offers a secluded Tuscan countryside retreat near major historical towns.
The 112 square metre property, spread over two levels, sleeps eight guests and includes a private terrace with barbecue, a shared seasonal swimming pool (May 2nd - October 3rd), and free parking; pets are welcome.
Podere Galieni - Certaldo
No reviews

Podere Galieni

house, Certaldo
Agriturismo 'Podere Galieni' is an elevated property in Certaldo, offering panoramic countryside views and situated 4 kilometres from the town centre, with San Gimignano 15 kilometres, Volterra 30 kilometres, Siena 35 kilometres, and Florence 40 kilometres away.
This spacious 250 square metre holiday cottage, renovated in 2025, accommodates up to 16 guests across 6 bedrooms and 8 bathrooms, featuring air conditioning, WiFi, a private swimming pool (seasonal April-October), and a terraced garden with local farm produce sales.
Belvilla By Oyo Casanova-apt14 - Certaldo
8.4 126 reviews

Belvilla By Oyo Casanova-apt14

house, Gambassi Terme
Belvilla by Oyo Casanova-apt14, a four-bedroom holiday home in Querce, is approximately 48 kilometres from Piazza Matteotti and 55 kilometres from Florence Airport.
This self-catering property boasts a private pool, garden, BBQ, and parking, sleeping up to eight guests and offering easy access to cycling and walking tours in the Tuscan countryside.
Casa Vacanze I Borghi - Certaldo
8.3 6 reviews

Casa Vacanze I Borghi

house, San Gimignano
This holiday home is located in San Gimignano, offering garden views and situated approximately 40 kilometres from Piazza Matteotti and 43 kilometres from Piazza del Campo.
Guests can enjoy air-conditioned rooms, free WiFi, a kitchen with a dishwasher, and an outdoor swimming pool, with free private parking also available.

Delightful Family-Friendly Houses in Certaldo

Share home-cooked meals and enjoy plenty of room for all ages inside family houses in Certaldo.

House With Terrace Overlooking Tuscan Countryside - Certaldo
9.9 35 reviews

House With Terrace Overlooking Tuscan Countryside

house, San Gimignano
This Tuscan villa, located between San Gimignano and Certaldo, offers easy access to Siena, which is 48 kilometres away, and Florence, 80 kilometres distant.
This family-friendly apartment accommodates up to five guests across two double bedrooms, featuring a panoramic terrace with views of the Tuscan countryside, a fully equipped kitchen, air conditioning, and private covered parking.
La Corte D'elsa - Tuscan Farmhouse With Pool - Certaldo
9.7 32 reviews

La Corte D'elsa - Tuscan Farmhouse With Pool

gîte, Castelfiorentino
La Corte d'Elsa, a farmhouse near Castelfiorentino in the Florentine hills, offers a convenient base for exploring Tuscany, being just 3km from Castelfiorentino's town centre with its supermarkets, restaurants and train station.
This 100m² self-catering apartment, Corte 1, sleeps up to six guests and boasts two bedrooms, two bathrooms, a private terrace, shared pool and garden, plus amenities including air conditioning, a dishwasher and satellite TV.
La Ripa - Appartamento Il Fienile - Certaldo
9.4 201 reviews

La Ripa - Appartamento Il Fienile

house, San Gimignano
La Ripa - Appartamento Padronale is a short distance from San Gimignano's historic centre, making it easy to explore the town's charming streets and iconic towers. The property has received excellent ratings for its location, cleanliness and overall experience.
This two-bedroom house offers comfortable accommodation for families or groups of friends. It has a private patio with garden views, a shared swimming pool, a fully equipped kitchen and free Wi-Fi.
Casa Al Cantone - Certaldo
9.8 17 reviews

Casa Al Cantone

house, Certaldo
This one-bedroom apartment is situated in the heart of Certaldo, directly opposite the Palazzo Pretorio, offering easy access to the town's attractions.
The apartment comfortably sleeps five guests and includes a fully equipped kitchen, a private terrace with views of the historic district, and modern amenities such as air conditioning, Wi-Fi, and a washing machine.

Frequently asked questions about villa rentals in Certaldo

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

    Certaldo is a beautiful medieval town with plenty to see. The main attraction is the Casa di Boccaccio, the house where the famous writer Giovanni Boccaccio was born. The Palazzo Pretorio, a 14th-century building, is also worth a visit, and offers beautiful views of the Val d'Elsa valley from its tower. For a bit of history, head to the Museo di Arte Sacra and the Museo di Palazzo Pretorio. And for a fantastic view of the countryside, take the funicular railway up to the Rocca di Certaldo Alto.
  • What are the best villa rentals in Certaldo?

    Among the villa rentals in Certaldo, Il Rosolaccio, Casa Badia and Piccolo Cottage San Gimignano are the most popular ones.

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

    Certaldo is situated in the heart of Tuscany, so you'll see plenty of wildlife. Keep an eye out for birds of prey like buzzards and kestrels, and if you're lucky, you might spot a fox or a wild boar in the surrounding forests. You can also find a variety of reptiles and amphibians in the area, including lizards, snakes, and frogs.
  • What are the best villa rentals with a pool in Certaldo?

  • What is the best time to visit Certaldo?

    Spring and autumn are the best times to visit Certaldo. The weather is mild and pleasant, and the crowds are smaller than in the summer months. You'll also find that the hills surrounding Certaldo are particularly beautiful during these seasons, with vibrant colours and blooming wildflowers.
  • What are the best villa rentals with a jacuzzi in Certaldo?

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

    The easiest time to book a villa rental in Certaldo is during the shoulder seasons, from April to May and September to October. You'll get better rates and less competition for the best properties.
  • 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 Piccolo Cottage San Gimignano.

  • What are the top hiking trails near Certaldo?

    There are many great hiking trails around Certaldo. One of the most popular is the Sentiero del Boccaccio, which follows the path that Boccaccio took to reach the Fonte di Boccaccio, a spring that was once a vital source of water for the town. Another great option is the Sentiero delle Crete, a circular trail that takes you through the rolling hills and vineyards of the Val d'Elsa.
  • What are the best pet friendly villa rentals in Certaldo?

    The best pet friendly villa rentals in Certaldo are Il Rosolaccio, Casa Badia and Piccolo Cottage San Gimignano.

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

    Renting a villa in Certaldo offers a lot of advantages. You'll have more space and privacy than in a hotel, and you'll be able to enjoy the peace and quiet of the Tuscan countryside. You'll also be able to cook your own meals, which can save you money and give you more flexibility.
  • What are the best villa rentals with parking in Certaldo?

    Il Rosolaccio, Casa Badia and Piccolo Cottage San Gimignano are the best villa rentals with parking in Certaldo.

  • Are there popular destinations near Certaldo?

    Yes, there are many popular destinations near Certaldo. Florence is only a short train ride away, and Siena is also easily accessible by car. If you're interested in wine, you can visit the Chianti Classico region, which is just a short drive from Certaldo. And for a day trip to the beach, you can head to Versilia on the Tuscan coast.

Popular destinations

Best Certaldo villas and holiday homes with parking

Le Fonti A San Giorgio - Certaldo
9.2 158 reviews

Le Fonti A San Giorgio

farm, Montespertoli
Le Fonti a San Giorgio is a farmhouse located in the Chianti region, just 30km from Florence and 20km from San Gimignano, offering stunning views of the surrounding vineyards and olive groves. The property has been highly rated by previous guests for its cleanliness, location and overall experience.
This farmhouse offers a range of comfortable rooms, each with unique decor and a cosy atmosphere. Guests can enjoy a variety of amenities, including a swimming pool, a restaurant serving traditional Tuscan cuisine, and a charming garden where they can relax and soak up the peaceful surroundings.
Casa Ary Tra Firenze E Siena - Certaldo
9.5 74 reviews

Casa Ary Tra Firenze E Siena

house, Castelfiorentino
This family-friendly apartment in Castelfiorentino, Val d'Elsa, offers easy access to San Gimignano (approx. 25km), Certaldo Alto (approx. 10km), and Florence (approx. 50km), ideal for exploring Tuscany.
The two-bedroom, one-bathroom flat sleeps four, features a kitchen, internet, private parking, and provides all modern conveniences for a comfortable stay.
La Ripa - Appartamento I Nidi - Certaldo
8.7 3 reviews

La Ripa - Appartamento I Nidi

house, San Gimignano
La Ripa - Appartamento I Nidi is a self-catering property in San Gimignano, approximately 34km from Piazza Matteotti and 37km from Piazza del Campo, offering easy access to Tuscany's major attractions.
This 70 square metre house sleeps up to 12 guests in two bedrooms and one bathroom, and boasts a private pool, free Wi-Fi, free parking, a fully equipped kitchen, barbecue, children's playground, and a garden.
Il Piccolo Borgo - Quadrilocale - Certaldo
9.3 3 reviews

Il Piccolo Borgo - Quadrilocale

house, Certaldo
Il Piccolo Borgo - Quadrilocale, a four-bedroom holiday home in Certaldo, is situated approximately 35km from Florence, offering easy access to attractions such as the Pitti Palace and Piazza Matteotti.
This 75 square metre property sleeps up to 10 guests and boasts a private patio, garden with barbecue, hot tub, free Wi-Fi, parking, and is close to golfing, cycling and hiking opportunities.

Best Certaldo villas and holiday homes with a garden

Sandra House - Certaldo - Certaldo
9.0 1 review

Sandra House - Certaldo

house, Certaldo
Sandra House, in Certaldo, is approximately 45-48km from Florence and its attractions including the Piazzale Michelangelo, Piazza Matteotti, Pitti Palace, and Ponte Vecchio.
This 70 square metre property offers one bedroom, one bathroom, sleeps eight guests, and boasts a private pool, fully equipped kitchen, peaceful garden, and free Wi-Fi.
Holiday Home Conte Francesco I-3 By Interhome - Certaldo
8.0 4 reviews

Holiday Home Conte Francesco I-3 By Interhome

house, Certaldo
Holiday Home Conte Francesco I-3, located in Aia Murata, Certaldo, is approximately 37-43km from Florence's Piazza Matteotti, Piazzale Michelangelo, Pitti Palace, and Strozzi Palace.
This 112 square metre property boasts four bedrooms, two bathrooms, sleeps fifteen guests, and includes a private swimming pool, garden, terrace, parking, and Wi-Fi; a fully equipped kitchen and washing machine are also provided.
Poderi Arcangelo - Certaldo
8.9 900 reviews

Poderi Arcangelo

farm, San Gimignano
Poderi Arcangelo is a farm stay located just a 10-minute drive from the historic town of San Gimignano, nestled in the peaceful Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The farm is spread across three restored farmhouses, each with its own private pool, surrounded by olive groves, vineyards, and fields. Guests can enjoy a range of amenities, including a restaurant serving farm-fresh cuisine, a communal terrace with panoramic views, free Wi-Fi, and a variety of activities like guided tours and food tastings.
70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Certaldo
No reviews

70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Certaldo
Farm for 4 people. Your accommodation will be located in Certaldo.
Services and facilities: free parking, a kitchen and a garden.

Uncover Luxury Holiday Homes in Certaldo

Treat yourself to high-end design, custom furniture, and premium finishes at luxury small-city houses in Certaldo.

Agriturismo Renai E Monte Ii - Certaldo
9.4 169 reviews

Agriturismo Renai E Monte Ii

farm, Gambassi Terme
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