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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.

Tenuta Bartoli - Certaldo
9.9 25 reviews

Tenuta Bartoli

farm, San Gimignano
This working farm, Tenuta Bartoli, offers an authentic Tuscan experience just 3 kilometres from the historic hill town of San Gimignano, with Colle di Val d’Elsa and Poggibonsi a 20-minute drive away and Siena 45 kilometres distant.
Guests can enjoy rustic rooms, a regional restaurant, a swimming pool, a spa, and a garden, with free Wi-Fi available in public areas, though a private vehicle is recommended due to limited public transport.
450 M² Villa ∙ 5 Bedrooms ∙ 10 Guests - Certaldo
No reviews

450 M² Villa ∙ 5 Bedrooms ∙ 10 Guests

house, Certaldo
Villa Bellavista, in Certaldo, offers a spacious 450 square metre property with convenient access to Certaldo's historic centre.
This large holiday home sleeps up to 10 guests in 5 bedrooms and 7 bathrooms, boasting a private heated pool, jacuzzi, extensive garden, and ample parking; additional amenities include Wi-Fi, air conditioning, and access to locally produced olive oil and bicycle rentals.
"A Casa Di Franca Villa Con Piscina" - Certaldo
10 1 review

"A Casa Di Franca Villa Con Piscina"

house, Gambassi Terme
This spacious villa is situated in Gambassi Terme, Tuscany, 1.9km from Agricola Tamburini Emanuela and within 9.7km of Teatro del Popolo and Palazzo Pretorio.
The 223 square metre property boasts four bedrooms, three bathrooms, sleeps twelve guests, and includes a private pool, garden, parking, and a fully equipped kitchen with dishwasher.
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 gîte is situated just a short distance from the heart of Montespertoli, within easy reach of the Piazza Machiavelli, Montespertoli City Hall, and Piazza del Popolo. The surrounding area is peaceful and picturesque, offering a taste of authentic Tuscan life.
The gîte itself offers a comfortable and spacious layout, perfect for families or groups. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, tennis court, and a restaurant serving delicious local cuisine, ensuring a relaxing and enjoyable stay.

Delightful Family-Friendly Houses in Certaldo

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

Sangi Chianti Vacations - Certaldo
9.4 20 reviews

Sangi Chianti Vacations

house, Poggibonsi
This recently renovated holiday home is located in Poggibonsi, just 45 kilometres from Florence's Pitti Palace and 30 kilometres from Siena's Fontebranda, offering easy access to the region's rich history and culture. The property consistently receives excellent ratings for cleanliness, location and overall user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom property spans 90 square metres and comfortably accommodates up to five guests. The accommodation offers a range of amenities, including a private patio with garden views, a well-equipped kitchen, a garden with barbecue facilities, air conditioning, free Wi-Fi, and private parking.
Sangi Home - Certaldo
9.5 2 reviews

Sangi Home

house, San Gimignano
Sangi Home, a spacious holiday property in San Gimignano, is situated a short drive (approximately 39km and 43km respectively) from Piazza Matteotti and Piazza del Campo in Siena.
This 140 square metre house features two bedrooms, two bathrooms, sleeps up to 15 guests, and includes amenities such as a dishwasher, microwave, air conditioning, Wi-Fi, a terrace with city views, and a private patio.
Agriturismo Di Cabbiavoli - Certaldo
8.3 8 reviews

Agriturismo Di Cabbiavoli

farm, Castelfiorentino
Agriturismo Cabbiavilloli is an authentic working farm estate set amidst vineyards and olive groves, located 3 kilometres from Castelfiorentino train station, offering straightforward access to Florence (50 minutes), Siena (1 hour), and Pisa (1 hour 10 minutes).
This family-friendly agriturismo provides spacious apartments with traditional Tuscan features, a panoramic swimming pool, large outdoor areas, and accommodates up to 42 guests, making it suitable for groups and families seeking a tranquil rural base with convenient travel links.
Casa Villa Il Boschetto - Certaldo
9.9 49 reviews

Casa Villa Il Boschetto

house, Certaldo
Casa VILLA IL BOSCHETTO, a luxurious villa rental in Certaldo, is situated 34 kilometres from the Pitti Palace and Piazza Matteotti, offering a peaceful retreat.
This self-catering property boasts a private hot tub, fitness centre, swimming pool, and extensive gardens, perfect for families seeking relaxation and access to cycling routes near Certaldo.

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

Poderi Arcangelo - Certaldo
8.9 892 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.
Tenuta Sovestro - Agriturismo E Winery - Certaldo
9.5 1542 reviews

Tenuta Sovestro - Agriturismo E Winery

farm, San Gimignano
Tenuta Sovestro, a farmhouse stay near San Gimignano, is conveniently located 35km from both Piazza del Campo and Piazza Matteotti, offering a peaceful retreat yet within easy reach of this Tuscan town and Florence Airport (56km away).
This self-catering property features a bedroom, bathroom, and can accommodate two guests, boasting a swimming pool, restaurant, bar, free Wi-Fi, private parking, and a daily continental breakfast; a free shuttle service to San Gimignano is also provided.
Tenuta Di Sticciano - Certaldo
8.6 224 reviews

Tenuta Di Sticciano

farm, Certaldo
Tenuta Di Sticciano is a farm stay located in the Tuscan countryside, a short drive from the charming town of Certaldo and within easy reach of other popular destinations like Montespertoli and San Gimignano. This property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The farm stay offers a peaceful retreat with traditional Tuscan charm. Guests can enjoy a range of amenities including an outdoor pool, a spa, and a restaurant, as well as activities like wine and olive oil tastings.
Agriturismo Villa Gorgognano - Certaldo
9.7 203 reviews

Agriturismo Villa Gorgognano

farm, Certaldo
Agriturismo Villa Gorgognano is a family-friendly farmhouse situated in Certaldo, Tuscany, approximately 35 kilometres from Florence's Piazza Matteotti, Strozzi Palace, and Pitti Palace.
This one-bedroom, one-bathroom property offers guests a garden, private parking, Wi-Fi, air conditioning, and a daily buffet breakfast, plus features such as an outdoor fireplace and barbecue (seasonal).

Best Certaldo villas and holiday homes with a garden

Antico Casolare - Certaldo
9.6 224 reviews

Antico Casolare

farm, San Gimignano
Antico Casolare is a farm stay located just outside the centre of San Gimignano, a short 100-metre walk from the town's main attractions and within 150 metres of the bus stop to Siena. It has excellent ratings for user experience, location and cleanliness.
The farm offers a single bedroom and bathroom, with a private entrance and a furnished garden. Guests can enjoy modern amenities such as free Wi-Fi, flat-screen TVs and private bathrooms with free toiletries and hairdryers, as well as participate in the olive and grape harvest, experiencing the farm's agricultural life firsthand.
House With View Overlooking Tuscan Countryside - Certaldo
9.9 35 reviews

House With View 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.
Agriturismo Montegonfoli - Certaldo
9.5 285 reviews

Agriturismo Montegonfoli

farm, San Gimignano
Agriturismo Montegonfoli is situated just 5km from the historic walled city of San Gimignano, surrounded by vineyards and olive groves in the Tuscan countryside. The farm consistently receives excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers a range of well-appointed rooms and apartments, each with its own private outdoor space. Guests can enjoy a shared barbecue area in the garden, take a dip in the outdoor pool, and explore the surrounding countryside on horseback.
Agriturismo Il Castagnolino - Certaldo
8.4 682 reviews

Agriturismo Il Castagnolino

farm, San Gimignano
Il Castagnolino is a farmhouse located just 3 kilometres from the medieval town of San Gimignano and 30 kilometres from Volterra, offering a peaceful escape from the hustle and bustle of Tuscany. It has received very good user ratings, with excellent scores for location and cleanliness.
The farmhouse has one bedroom and one bathroom, decorated with traditional furnishings and antique ceilings. Guests can enjoy a swimming pool, a terrace, a garden, a restaurant, a cooking school, and an on-site shop selling fresh produce from the farm.

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 Azienda Agricola La Roccaia - Certaldo
9.0 364 reviews

Agriturismo Azienda Agricola La Roccaia

farm, San Gimignano
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