Search holiday homes in Certaldo from 100+ sites!

19 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

19 Villa rentals in Certaldo

Villa Fiorentini 10, Emma Villas - Certaldo
10 1 review
Certaldo
07/25 – 08/08
$1560/nighttotal: $21840 (14 )

Villa Fiorentini 10, Emma Villas

5 8
house, Barberino Tavarnelle
Villa Fiorentini 10, located in Barberino di Val d’Elsa, is just 14 miles from Piazza Matteotti and offers easy access to the Chianti region, with Pitti Palace and Strozzi Palace both within a 21-mile radius. This Emma Villas rental has received excellent user ratings for cleanliness and a very good location rating.
The 3770 square foot house has five bedrooms, two living rooms, a fully equipped kitchen, and six bathrooms. This villa offers a private pool, a terrace with pool views, a barbecue area, a solarium, a garden, and free Wi-Fi, satellite TV, and private parking.
Podere Casato - Certaldo
9.6 43 reviews
Certaldo
07/15 – 07/19
$195/nighttotal: $780 (4 )

Podere Casato

1 2
farm, Montespertoli
Podere Casato, a farm stay in Montespertoli, Tuscany, is located approximately 30 kilometers from Florence's Piazza Matteotti and Santa Maria Novella train station, and 34 kilometers from Florence Airport.
This one-bedroom, one-bathroom rental offers a private pool with Tuscan countryside views, free Wi-Fi, private parking, a fully equipped kitchen, barbecue facilities, a private terrace and garden, and is pet-friendly (fees apply).
La Casa Torre Di Marcello - Certaldo
9.9 175 reviews
Certaldo
07/16 – 07/18
$167/nighttotal: $334 (2 )

La Casa Torre Di Marcello

1 2
house, Certaldo
La casa torre di Marcello, a Certaldo house rental, is located about 25 miles from Florence's Pitti Palace and Piazza Matteotti, and 30 miles from Florence Airport, offering easy access to these Tuscan landmarks.
This 700-square-foot (approximately 65-square-meter) one-bedroom, one-bathroom dwelling features a fully equipped kitchen, private terrace, garden, parking, and amenities including complimentary wine and Wi-Fi; it comfortably accommodates two guests.
Cosy Apartment For 6 People With Pool, Wifi, Tv And Pets Allowed, Close To San Gimignano - Certaldo
10 5 reviews
Certaldo
06/27 – 07/04
$143/nighttotal: $1001 (7 )

Cosy Apartment For 6 People With Pool, Wifi, Tv And Pets Allowed, Close To San Gimignano

1 2
farm, Gambassi Terme
This farmhouse rental is located in Gambassi Terme, just a short drive from the Benozzo Gozzoli Museum and Teatro del Popolo, offering a peaceful escape from the city. Guests have consistently rated this property as excellent.
The rural lodging features a private garden and terrace, perfect for relaxing and enjoying the fresh air. The rental includes amenities like a kitchen, swimming pool, and tennis court, providing a comfortable and enjoyable stay.
Casetta Rossa - Certaldo
9.6 14 reviews
Certaldo
06/26 – 06/29
$190/nighttotal: $570 (3 )

Casetta Rossa

2 2
house, Certaldo
Casetta Rossa is a charming house located in Certaldo, a picturesque town just 25 miles from Florence and its famous landmarks like Piazza Matteotti, Strozzi Palace, and Ponte Vecchio. This family-friendly rental has received excellent ratings for its cleanliness, location, and overall experience.
The home features two bedrooms and two bathrooms, comfortably accommodating up to four guests. It boasts a fully equipped kitchen with a dishwasher, a relaxing living room with a flat-screen TV, and convenient amenities like towels and bed linens.
Agriturismo Lucciano - Certaldo
9.5 143 reviews
Certaldo
07/25 – 08/08
$436/nighttotal: $6104 (14 )

Agriturismo Lucciano

4 8
farm, Montespertoli
Agriturismo Lucciano, located in San Casciano in Val di Pesa, offers a convenient base for exploring Tuscany, situated approximately 8-9 miles from Florence's iconic attractions like the Pitti Palace, Piazza Matteotti, and the Strozzi Palace.
This family-friendly farmhouse rental boasts a private terrace, garden, tennis court, and fully equipped kitchen including a refrigerator and microwave, plus free Wi-Fi and parking; a paid airport shuttle to Florence Airport is also available.
Villa Boccaccio - Certaldo
Certaldo
07/16 – 07/18
$1019/nighttotal: $2038 (2 )

Villa Boccaccio

6 2
house, San Gimignano
This villa is located in San Gimignano, 12 miles from Tenuta Torciano winery and 13 miles from Casa Boccaccio.
This 3,770 square foot villa sleeps 12 guests with 6 bedrooms and 4 bathrooms, featuring a well-equipped kitchen, air conditioning, Wi-Fi, a jacuzzi, garden, terrace, barbecue, and is ideal for exploring local cultural sites and outdoor adventures.
Spacious Tuscany Retreat - Certaldo
10 3 reviews
Certaldo
06/27 – 07/04
$384/nighttotal: $2688 (7 )

Spacious Tuscany Retreat

5 2
farm, Gambassi Terme
This Gambassi Terme farmhouse rental, located 0.8 miles from Agricola Tamburini Emanuela and within 6 miles of the Benozzo Gozzoli Museum and Teatro del Popolo, offers a peaceful rural setting near several Tuscan attractions.
This 1390-square-foot vacation home features five bedrooms, four bathrooms, and accommodates up to eleven guests, complete with a swimming pool, tennis court, garden, barbecue grills, and internet access.
The Garden House - Certaldo
8.5 41 reviews
Certaldo
07/25 – 08/08
$563/nighttotal: $7882 (14 )

The Garden House

4 8
house, Castelfiorentino
The Olive House is located in the Tuscan countryside, a short drive from the charming medieval town of Castelfiorentino and about 26 miles from Florence. The house consistently receives excellent ratings for its cleanliness, location, and overall experience.
This home features two bedrooms and a well-equipped kitchen, perfect for families or groups of friends. Enjoy the outdoor space with a private pool, a tennis court, and a garden, perfect for relaxing and enjoying the Tuscan sunshine.
60 M² House ∙ 1 Bedroom ∙ 4 Guests - Certaldo
10 2 reviews
Certaldo
07/15 – 07/18
$136/nighttotal: $408 (3 )

60 M² House ∙ 1 Bedroom ∙ 4 Guests

1 2
house, Montespertoli
Villa Il Frantoio, a pet-friendly Tuscan countryside rental near Montespertoli, is located 12 miles from Florence and offers easy access to Siena and Pisa.
This 650-square-foot house features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, private parking, Wi-Fi, a shared pool (June-September), tennis court, and access to an on-site wine cellar.
55 M² House ∙ 1 Bedroom ∙ 2 Guests - Certaldo
Certaldo
07/16 – 07/18
$318/nighttotal: $636 (2 )

55 M² House ∙ 1 Bedroom ∙ 2 Guests

1 2
house, San Gimignano
This Tuscan villa is located in Pancole, 6 miles from the historic town of San Gimignano, offering panoramic views of the surrounding vineyards and olive groves.
This 590 sq ft residence accommodates 2 guests with 1 bedroom and 1 bathroom, featuring air conditioning, a full kitchen, Wi-Fi, a private terrace, a shared swimming pool (operational June-October), and on-site parking.
La Quercia, Apartment With Garden For 6/8 People  In The Heart Of Chianti - Certaldo
10 2 reviews
Certaldo
07/25 – 08/08
$414/nighttotal: $5796 (14 )

La Quercia, Apartment With Garden For 6/8 People In The Heart Of Chianti

4 8
cottage, Montespertoli
This renovated cottage in Montespertoli is located in a rural area, offering proximity to landmarks like Castle of Poppiano and Castello Sonnino, and is near the Castelvecchio Natural Reserve.
This spacious 2370 sq ft house accommodates up to 8 guests across 4 bedrooms and 4 bathrooms, featuring a well-equipped kitchen with a dishwasher and fridge, air conditioning, internet, a garden, and parking.

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.

Villa Milani - Tenuta La Gigliola - Certaldo
8.1 67 reviews
Certaldo
07/15 – 07/19
$125/nighttotal: $500 (4 )

Villa Milani - Tenuta La Gigliola

1 2
house, Montespertoli
Fattoria la Gigliola - Villa Milani is a spacious villa in Montespertoli, Tuscany, about 20-22 miles from Florence's Duomo, Pitti Palace, and Piazza della Signoria.
This 8-bathroom villa, perfect for large groups, offers a private pool, garden with barbecue, free Wi-Fi, private parking, a games room with billiards and table tennis, and a terrace with garden views; nearby attractions include a restaurant and tennis court.
Fattoria Di Pancole - Certaldo
8.8 120 reviews
Certaldo
07/16 – 07/18
$283/nighttotal: $566 (2 )

Fattoria Di Pancole

2 2
farm, San Gimignano
Fattoria Di Pancole is a farm stay located just a 5-minute drive from the historic hill town of San Gimignano, surrounded by vineyards and olive groves in the Tuscan countryside. The property has received very good user ratings and excellent ratings for location and cleanliness.
The apartments feature traditional Tuscan design with terracotta floors and wood-beamed ceilings. Amenities include a swimming pool, private gardens, a bar, and a fully equipped kitchen, plus guests can enjoy wine tasting tours and experience the farm's award-winning wine and olive oil production.
Villa Le Cascine - Certaldo
Certaldo
07/25 – 08/08
$2108/nighttotal: $29512 (14 )

Villa Le Cascine

17 8
house, Montaione
Villa le Cascine, a large estate in Montaione, is located 31 miles from the Uffizi Gallery and Piazza della Signoria, and 29 miles from Piazzale Michelangelo and Montecatini Train Station.
This 5380-square-foot villa accommodates up to 57 guests in 17 bedrooms and 15 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, garden, and private parking, with WiFi included.
Belvilla By Oyo Fontana - Certaldo
8.8 317 reviews
Certaldo
09/19 – 10/03
$154/nighttotal: $2156 (14 )

Belvilla By Oyo Fontana

1 4
house, Castelfiorentino
This house is located in Bagnolo, a peaceful town about 25 miles from Florence's main attractions like Pitti Palace, Strozzi Palace, and Piazza della Signoria. The house has received very good ratings for user experience, location, and cleanliness.
The house is perfect for families with children, offering a shared pool, a playground, and a garden. It features a fully equipped kitchen, free Wi-Fi, air conditioning, and parking.

Best family friendly Certaldo villas and beach houses

Among the 19 accommodations in Certaldo, here are the 4 best family friendly villas and beach houses

632 M² Villa ∙ 6 Bedrooms ∙ 12 Guests - Certaldo
Certaldo
07/25 – 08/08
$1875/nighttotal: $26250 (14 )

632 M² Villa ∙ 6 Bedrooms ∙ 12 Guests

6 8
house, Castelfiorentino
This Tuscan countryside villa is located near Castelfiorentino, Italy, approximately 10 miles from San Miniato, 16 miles from San Gimignano, and 29 miles from Florence, offering easy access to major Tuscan towns.
This 6,800-square-foot estate boasts six bedrooms sleeping twelve, a private pool, spa, and ample parking, plus a fully equipped kitchen including a dishwasher and microwave, all within easy reach of restaurants such as Le Boscarecce and local wineries.
La Ripa - Appartamento I Ghiri - Certaldo
9.4 193 reviews
Certaldo
06/26 – 06/29
$380/nighttotal: $1140 (3 )

La Ripa - Appartamento I Ghiri

2 2
house, San Gimignano
La Ripa - Appartamento Padronale is located in San Gimignano, Tuscany, about 21 miles from Piazza Matteotti and 23 miles from Piazza del Campo, offering a peaceful retreat near the historic city center. This vacation rental has received excellent ratings for its location, cleanliness, and overall experience.
The property offers two spacious bedrooms with modern amenities, accommodating up to four guests. Enjoy a private patio with garden views, a refreshing dip in the outdoor swimming pool, and a fully equipped kitchen with a dishwasher and oven.
Grand Cherry Tree, 8 Beds - Certaldo
10 2 reviews
Certaldo
07/25 – 08/08
$290/nighttotal: $4060 (14 )

Grand Cherry Tree, 8 Beds

3 8
house, Certaldo
This Certaldo vacation home is conveniently located approximately 43 kilometers (27 miles) from Florence Airport and offers easy access to the historic center of Certaldo.
The one-bedroom house features two bathrooms, a fully equipped kitchen, free Wi-Fi, air conditioning, and sleeps up to 15 guests, perfect for families or large groups visiting Tuscany.
Agriturismo La Fidanza - Certaldo
8.5 19 reviews
Certaldo
07/15 – 07/18
$98/nighttotal: $294 (3 )

Agriturismo La Fidanza

1 2
farm, San Gimignano
Agriturismo La Fidanza is located in San Gimignano, 23 miles from Piazza Matteotti and 26 miles from Piazza del Campo, with Florence Airport 34 miles away.
This farm stay offers air-conditioned units with kitchenettes, complimentary WiFi, private parking, a seasonal outdoor pool, and a garden with barbecue facilities and an outdoor fireplace, with check-out between 8 AM and 11 AM.

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.

Destinations nearby

Best Certaldo houses with parking

Podere La Torre - Certaldo
Certaldo
06/27 – 07/04
$158/nighttotal: $1106 (7 )

Podere La Torre

1 2
farm, Certaldo
Podere La Torre is a renovated farmhouse located just outside of Certaldo Alto, a charming hilltop town with stunning views of the Tuscan countryside. The historic center of Certaldo Alto is a short walk away, and other popular Tuscan destinations like San Gimignano, Florence, and Siena are all within easy driving distance.
The farmhouse offers a comfortable and spacious one-bedroom apartment with a kitchen, bathroom, and terrace, perfect for a group of up to four guests. Enjoy the peaceful surroundings, relax by the seasonal pool, grill up a meal on the barbecue, and take advantage of the on-site amenities, including internet access, a washing machine, and an electric vehicle charging station.
Agriturismo Poggio Ai Grilli - Certaldo
9.6 40 reviews
Certaldo
06/27 – 07/04
$142/nighttotal: $994 (7 )

Agriturismo Poggio Ai Grilli

1 2
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.
Ripabella - Certaldo
9.3 103 reviews
Certaldo
07/15 – 07/20
$326/nighttotal: $1630 (5 )

Ripabella

1 2
house, San Gimignano
Ripabella, an adults-only vacation home in San Gimignano, is located 21 miles from Piazza Matteotti and 24 miles from Piazza del Campo in Siena.
This one-bedroom, one-bathroom rental sleeps two guests and boasts a private pool, Jacuzzi, fitness center, and fully equipped kitchen with a dishwasher, plus free Wi-Fi and private parking.
90 M² House ∙ 2 Bedrooms ∙ 4 Guests - Certaldo
Certaldo
09/19 – 10/03
$189/nighttotal: $2646 (14 )

90 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 4
house, San Gimignano
This vacation rental is located in the Pancole hills, 3.7 miles from San Gimignano, between Siena and Florence, surrounded by vineyards and olive groves.
This 970 sq ft house accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring a seasonal swimming pool, Wi-Fi, air conditioning, and a furnished terrace, with a nearby hotel bar and restaurant 100 yards away.

Best Certaldo houses with a garden

Agriturismo Il Torrione - Certaldo
9.0 59 reviews
Certaldo
06/27 – 07/04
$94/nighttotal: $658 (7 )

Agriturismo Il Torrione

1 2
farm, Certaldo
Agriturismo Il Torrione, a family-friendly farmhouse rental in Certaldo, Italy, is located about 25 miles from Florence's Pitti Palace and Piazza Matteotti, and 30 miles from Florence Airport.
This one-bedroom, one-bathroom rural property boasts a swimming pool, garden, barbecue facilities, free Wi-Fi, and free parking, plus accessibility features and children's amenities including a playground and kids' pool.
Anwesen "I Leonie" Mit Privatem Garten Und Grill - Certaldo
Certaldo
07/25 – 08/08
$1443/nighttotal: $20202 (14 )

Anwesen "I Leonie" Mit Privatem Garten Und Grill

10 8
house, Montespertoli
This Tuscan villa, located in the Chianti countryside just 0.56 miles (900 meters) from Montespertoli, offers exceptional panoramic views and is conveniently situated between Florence and Siena.
This expansive 4410 square foot estate includes 10 bedrooms and 9 bathrooms to accommodate up to 19 guests, featuring a private pool, extensive grounds with a garden and barbecue area, and is well-equipped for self-catering with multiple kitchens, making it an ideal base for exploring Tuscany.
Apartment Giuggiolo - Giuggiolo 5 By Interhome - Certaldo
8.7 112 reviews
Certaldo
09/19 – 10/10
$71/nighttotal: $1491 (21 )

Apartment Giuggiolo - Giuggiolo 5 By Interhome

2 4
apartment, Poggibonsi
Apartment Giuggiolo, located in Bibbiano, a short drive from Poggibonsi and approximately 30 kilometers (19 miles) from Siena's Piazza Matteotti and Piazza del Campo, offers a convenient base for exploring Tuscany.
This three-bedroom, three-bathroom rental boasts a fully equipped kitchen with dishwasher, private terrace and garden, free parking, Wi-Fi, and a swimming pool; it comfortably sleeps families or groups.
Agriturismo Pompone E Pola - Certaldo
Certaldo
07/25 – 08/08
$423/nighttotal: $5922 (14 )

Agriturismo Pompone E Pola

5 8
house, Gambassi Terme
Agriturismo Pompone e Pola in Gambassi Terme, Tuscany, offers a peaceful retreat approximately 58 kilometers from Florence Airport, providing easy access to the Tuscan countryside.
This family-friendly vacation home rental features fully equipped kitchenettes, free Wi-Fi, private parking, a shared lounge, and a picnic area; pets are welcome.
©2026 cozycozy.com