Compare Vacation Rentals & Airbnb in Certaldo

125 available vacation rental offers

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

125 Rentals and Airbnb in Certaldo

Best family friendly Certaldo vacation rentals

Among the 125 accommodations in Certaldo, here are the 4 best family friendly rentals

Montegonfoli 4, Apartment For 4 Adults With Amazing Views On San Gimignano - Certaldo
9.6 135 reviews
Certaldo
29/08 – 06/09
$257/nighttotal: $2056 (8 )

Montegonfoli 4, Apartment For 4 Adults With Amazing Views On San Gimignano

2 5
farm , San Gimignano
This charming gîte is located just 5km from San Gimignano, in a peaceful rural setting close to Tenuta Torciano Winery, Sant'Agostino Church, and the Archaeological Museum. It has received excellent ratings for location, cleanliness, and overall experience.
The 80 square metre property sleeps up to 5 guests and offers two bedrooms and two bathrooms. Enjoy a range of amenities including a private swimming pool, jacuzzi, terrace, garden, and barbecue facilities.
Villa Tegolato - Certaldo
Certaldo
25/07 – 08/08
$3241/nighttotal: $45374 (14 )

Villa Tegolato

8 8
house , Barberino Tavarnelle
This villa is located in Tavarnelle Val di Pesa, within the Chianti region, 17.7 kilometres from Piazza Matteotti and 29 to 30.6 kilometres from Florence's Piazzale Michelangelo and Uffizi Gallery.
Il Boscone offers 8 bedrooms and 8 bathrooms across 455 square metres, accommodating up to 42 guests with air conditioning, a swimming pool, jacuzzi, garden, parking, and a fully equipped kitchen featuring a fridge, microwave, and dishwasher, with facilities for disabled guests also available.
90 M² House ∙ 2 Bedrooms ∙ 4 Guests - Certaldo
Certaldo
04/07 – 05/07
$2287/nightfor 1 night

90 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 4
house , San Gimignano
This San Gimignano holiday home, 7km from the medieval town, enjoys a convenient location midway between Siena and Florence, ideal for exploring Tuscany.
The 90 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a private garden with barbecue, shared swimming pool, and high-speed Wi-Fi.
Casa Lenzona 2 - Certaldo
Certaldo
23/06 – 30/06
$240/nighttotal: $1680 (7 )

Casa Lenzona 2

2 2
apartment , Certaldo
This Certaldo apartment, Casa Lenzona 2, is located 35 kilometres from Piazza Matteotti, with Piazzale Michelangelo and the Uffizi Gallery approximately 42 to 43 kilometres away.
This 70 square metre rental offers accommodation for up to 7 guests, featuring 1 bedroom, 2 bathrooms, air conditioning, free Wi-Fi, a fully equipped kitchen with a dishwasher, and private parking is available for an additional charge.

Best Certaldo vacation rentals with parking

Wonderful Private Villa For 16 People With A/c, Wifi, Private Pool, Tv, Patio And Panoramic View - Certaldo
Certaldo
25/07 – 08/08
$2023/nighttotal: $28322 (14 )

Wonderful Private Villa For 16 People With A/c, Wifi, Private Pool, Tv, Patio And Panoramic View

6 8
apartment , Certaldo
This holiday cottage in the Tuscan countryside offers panoramic views of San Gimignano and is located 4 kilometres from Certaldo centre, with local farm products available on-site.
The 250 square metre property across three levels accommodates up to 16 guests in six bedrooms and eight bathrooms, featuring air conditioning, WiFi, a private swimming pool (seasonal, 1 April - 31 October), and private parking.
Conte Francesco Ii - Certaldo
Certaldo
23/06 – 30/06
$165/nighttotal: $1155 (7 )

Conte Francesco Ii

2 1
apartment , Certaldo
This two-bedroom apartment, situated on a vineyard estate 7km from Certaldo, 13km from San Gimignano, and 57km from Florence, offers a secluded location with stunning countryside views.
The 60 square metre property features a terrace with barbecue, a private garden, a swimming pool (seasonal), parking, and accommodates up to four guests, with amenities including Wi-Fi and a kitchen equipped with a freezer.
In Centro A Certaldo - Certaldo
9.2 23 reviews
Certaldo
03/08 – 06/08
$219/nighttotal: $657 (3 )

In Centro A Certaldo

2 2
apartment , Certaldo
This Certaldo apartment, conveniently located in the town centre, is approximately 42 kilometres from Florence's Piazzale Michelangelo and Pitti Palace.
The 70-square-metre self-catering property boasts a one-bedroom layout sleeping up to 11 guests, featuring a private garden, terrace, balcony, parking, air conditioning, Wi-Fi, and BBQ facilities.
Luca's Home - Certaldo
8.8 17 reviews
Certaldo
17/07 – 19/07
$249/nighttotal: $498 (2 )

Luca's Home

2 2
apartment , San Gimignano
Luca's home is a self-catering apartment in San Gimignano, conveniently located 35km from Florence Airport and 35km from both Siena's Piazza del Campo and Piazza Matteotti.
This 56 square metre property sleeps seven guests in two bedrooms and two bathrooms, and includes free Wi-Fi, private parking, a dishwasher, washing machine, and all linen and towels.

Frequently Asked Questions about vacation rentals in Certaldo

  • What are some interesting places to visit in or near Certaldo?

    Certaldo is a charming medieval town with plenty to see. The historic centre, perched on a hilltop, is a must-visit. You can find the house of Boccaccio, the famous Italian writer, there. Just outside of Certaldo, you'll find the Castello di Oliveto, a beautiful 12th-century castle, which is worth a trip.
  • What are the best Airbnb and vacation rentals in Certaldo?

    Il Rosolaccio, La Casina Di Ancicucco 1 and La Casina Di Ancicucco 2 are the most popular Airbnb and vacation rentals in Certaldo among travelers.

  • Which walking or cycling routes are the best in Certaldo?

    For a scenic walk, take the Sentiero del Boccaccio, a trail that winds through the Tuscan countryside, offering stunning views of the surrounding hills. For cycling, the Via Francigena, an ancient pilgrimage route, passes through Certaldo and offers a challenging but rewarding ride.
  • What are the most popular Airbnbs in Certaldo?

    Among the Airbnbs in Certaldo, La Casina Di Ancicucco 1, La Casina Di Ancicucco 2 and Country House Nazzano Près S -gimignano -Lulico are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Certaldo?

    Certaldo is a great place for outdoor activities. You can go hiking in the surrounding hills, play tennis at the local courts, or try your hand at horseback riding at one of the nearby stables. There are also several golf courses within easy reach.
  • What are the best vacation rentals with a pool in Certaldo?

  • What other towns or cities can be easily accessed from Certaldo?

    Certaldo is well-connected to other Tuscan towns. You can easily reach Florence, Siena, and San Gimignano by car or train. Pisa and Lucca are also within a reasonable distance for a day trip.
  • What are the best rentals for families and kids in Certaldo?

    The best rentals for families and kids in Certaldo are Il Rosolaccio, La Casina Di Ancicucco 1 and La Casina Di Ancicucco 2.

  • What amenities are commonly available in vacation rentals in Certaldo?

    Vacation rentals in Certaldo typically offer a range of amenities, including kitchens, laundry facilities, Wi-Fi, and private outdoor spaces. Some rentals also have swimming pools or hot tubs. You can find rentals that suit your needs and budget.
  • What are the best rentals or Airbnbs with a jacuzzi in Certaldo?

    The best vacation rentals or Airbnb with a jacuzzi in Certaldo are Tognazzi Casa Vacanze - La Collina Di San Gimignano, Borgo Dei Cadolingi and Villa Boccaccio.

  • What time of year is best to rent a vacation rental Certaldo?

    The best time to visit Certaldo is during the spring or autumn, when the weather is mild and the crowds are smaller. Summer can be hot and crowded, while winter can be chilly and wet.
  • What are the local dishes in Certaldo region?

    The local cuisine in Certaldo is a true delight. Try the 'Ribollita', a hearty bread soup with vegetables, or the 'Pici cacio e pepe', a simple but delicious pasta dish with pecorino cheese and black pepper. Don't forget to sample the 'Chianti Classico' wine, produced in the nearby vineyards.

Destinations nearby

Best Certaldo vacation rentals with a balcony

Agriturismo Casa Alla Madonna - Certaldo
8.9 35 reviews
Certaldo
14/07 – 16/07
$210/nighttotal: $420 (2 )

Agriturismo Casa Alla Madonna

1 2
farm , San Gimignano
Casa Alla Madonna, a San Gimignano farmhouse stay, is situated approximately 39 kilometres from Piazza Matteotti and 43 kilometres from the Pitti Palace, with Florence Airport 52 kilometres away.
This self-catering property offers one bedroom, one bathroom, a kitchen equipped with a fridge, microwave, and dishwasher, plus free Wi-Fi, private parking, and air conditioning; guests can also enjoy a terrace, garden, bar, and facilities for disabled guests, along with bike rentals and breakfast options.
Villa Milani - Tenuta La Gigliola - Certaldo
8.1 67 reviews
Certaldo
08/08 – 15/08
$516/nighttotal: $3612 (7 )

Villa Milani - Tenuta La Gigliola

3 5
house , Montespertoli
Fattoria la Gigliola - Villa Milani is a spacious villa in Montespertoli, Tuscany, approximately 32-35km from Florence's historical centre, including the Strozzi Palace, Piazza Matteotti, Santa Maria Novella, Pitti Palace, Piazza della Signoria, and the Florence Cathedral.
This eight-bathroom property, perfect for large groups, boasts a private pool, garden with barbecue, free Wi-Fi, parking, and on-site recreation including billiards and table tennis, alongside a well-equipped kitchen and terrace.
Tuscany Hills La Veduta - Certaldo
9.3 33 reviews
Certaldo
03/08 – 06/08
$385/nighttotal: $1155 (3 )

Tuscany Hills La Veduta

1 2
apartment , Certaldo
Tuscany Hills La Veduta apartment in Certaldo offers a convenient base for exploring Tuscany, situated approximately 32km from Piazza Matteotti and 42km from the Pitti Palace and Piazzale Michelangelo.
This 62 square metre self-catering property sleeps seven guests, boasting a private terrace, swimming pool, garden, parking (including electric vehicle charging), and a fully equipped kitchen; a picnic area is also available on-site.
Turignano Apartment - Certaldo
8.4 72 reviews
Certaldo
08/08 – 15/08
$356/nighttotal: $2492 (7 )

Turignano Apartment

1 5
apartment , Montespertoli
Turignano Apartment is a family-friendly dwelling located in Montespertoli, Tuscany, 22.5km from Florence, 38.6km from Siena, and 38.6km from Montecatini Terme, offering easy access to major Tuscan cities.
This two-bedroom property sleeps eight guests and boasts a private garden, swimming pool, fitness centre, parking, and a terrace; barbecue facilities are also available for al fresco dining.

Best pet friendly Certaldo vacation rentals

Among the 125 accommodations in Certaldo, here are the 4 best pet friendly rentals

Holiday Home Conte Francesco Ii-6 By Interhome - Certaldo
Certaldo
29/08 – 06/09
$453/nighttotal: $3624 (8 )

Holiday Home Conte Francesco Ii-6 By Interhome

4 5
house , Certaldo
Holiday Home Conte Francesco II-6, situated in Aia Murata, is approximately 37-48km from Florence, offering a peaceful countryside escape near Certaldo.
This four-bedroom, two-bathroom villa boasts 120 square metres of space, a private pool, garden, parking, and Wi-Fi, comfortably sleeping up to 15 guests.
Anwesen "I Leonie" Mit Privatem Garten Und Grill - Certaldo
Certaldo
25/07 – 08/08
$2017/nighttotal: $28238 (14 )

Anwesen "I Leonie" Mit Privatem Garten Und Grill

10 8
house , Montespertoli
This country estate, a manor house and annexe, is situated in the Chianti countryside near Montespertoli, offering panoramic views and positioned between Florence and Siena, approximately 20 kilometres from Florence's centre.
This property provides accommodation for up to 19 guests across five flats, featuring 10 bedrooms and 9 bathrooms, with amenities including air conditioning, a private pool, a large garden with barbecue facilities, and 410 square metres of floor area, ideal for exploring hiking and cycling routes.
Villa 'Cimpoli Casa' Mit Garten Und Grill - Certaldo
Certaldo
25/07 – 08/08
$303/nighttotal: $4242 (14 )

Villa 'Cimpoli Casa' Mit Garten Und Grill

4 8
house , Chianni
This country house in Rivalto, a medieval village 300 meters from local amenities and 3 kilometers from Chianni, offers panoramic views of the Tuscan hills near Pisa.
The renovated 210 square meter farmhouse accommodates up to 9 guests across four bedrooms, featuring two bathrooms, a well-equipped kitchen, WiFi, and a garden with a veranda and barbecue.
Conte Francesco Ii By Interhome - Certaldo
8.0 1 review
Certaldo
29/08 – 06/09
$457/nighttotal: $3656 (8 )

Conte Francesco Ii By Interhome

4 5
apartment , Certaldo
This four-bedroom flat, accommodating up to eight guests, is located on a vineyard estate 4 kilometres from Certaldo town centre and 13 kilometres from San Gimignano, offering a secluded and sunny elevated position surrounded by nature.
The 120 square metre dwelling features two levels with rustic interiors, stone floors and fireplaces, a shared natural garden, orchard, seasonal swimming pool, terraces with outdoor furniture and barbecue, plus Wi-Fi and a washing machine, with a car recommended due to the 1.5 kilometre unpaved access road.
©2026 cozycozy.com