Compare best Airbnb in Poggibonsi from 100+ providers!

132 available vacation rental offers

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

Best Vacation rentals and Airbnb offers in Poggibonsi

Top Vacation Rentals for Families in Poggibonsi

Booking a family-oriented vacation rental in Poggibonsi keeps you close to top city attractions for a stress-free getaway.

Il Cestino Di Ciliege - Poggibonsi
Poggibonsi
08/05 – 08/12
$233/nighttotal: $1631 (7 )

Il Cestino Di Ciliege

3 5
apartment , Certaldo
This apartment is centrally located in Certaldo, providing easy access to Palazzo Comunale and Casa del Boccaccio, and is within 16 miles of Weingut Tenuta Torciano.
This family-friendly rental accommodates up to 7 guests in 3 bedrooms and 2 bathrooms, featuring a full kitchen with a microwave and dishwasher, on-site parking, and a garden.
Tuscan Chianti Villa Private Park 2 Apt Love Views - Poggibonsi
10 1 review
Poggibonsi
08/05 – 08/12
$316/nighttotal: $2212 (7 )

Tuscan Chianti Villa Private Park 2 Apt Love Views

1 5
apartment , Poggibonsi
Villa Melachecca, a Tuscan villa in Agresto, is situated 4 minutes from Poggibonsi, offering proximity to the Chianti wine region.
This family-friendly villa accommodates up to 7 guests in 4 bedrooms and features 2 independent apartments that can be combined, a private garden with an outdoor dining area, air conditioning, internet, a kitchen with a freezer and microwave, and the unique opportunity to collect fresh eggs.
Oasi Luana 
 Colle Di Val D'elsa - Poggibonsi
10 23 reviews
Poggibonsi
09/23 – 09/24
$102/nightfor 1 night

Oasi Luana Colle Di Val D'elsa

1 2
apartment , Colle di Val d'Elsa
This Colle di Val d'Elsa apartment offers easy access to Siena and Florence, with a CONAD supermarket and frequent bus service an 8-minute walk away.
The two-bedroom, one-bathroom rental sleeps three guests and includes a dishwasher, freezer, private parking, and a fitness center, making it an ideal base for exploring Tuscany.
Enjoyable Apartment In The Middle Of Tuscany! - Poggibonsi
8.0 2 reviews
Poggibonsi
09/20 – 09/21
$218/nightfor 1 night

Enjoyable Apartment In The Middle Of Tuscany!

2 1
apartment , Colle di Val d'Elsa
This Colle di Val d'Elsa apartment rental, conveniently located near the Alta Val d'Elsa River Park and Le Caldane Thermal Baths, offers easy access to local attractions and day trips to Siena and the Leonetto Comparini Anatomy Museum.
The two-bedroom, two-bathroom unit sleeps five, features a fully equipped kitchen with dishwasher, and includes amenities such as WiFi, a washing machine, and access to a swimming pool, spa, and garden.

Best Poggibonsi vacation rentals with parking

Poderi Arcangelo - Poggibonsi
8.8 1452 reviews
Poggibonsi
06/23 – 06/24
$696/nightfor 1 night

Poderi Arcangelo

3 7
farm , San Gimignano
Poderi Arcangelo is a farm located just outside San Gimignano, a 10-minute drive from the town center, offering a peaceful escape surrounded by Tuscan countryside. The farm receives very good ratings for cleanliness and user experience, and an excellent rating for its location. The property consists of three restored farmhouses, each with its own private pool, and a main building featuring an infinity pool and a communal terrace with panoramic views of San Gimignano. Guests can enjoy farm-to-table dining, guided tours, food tastings, and free Wi-Fi throughout the property.
Holiday Home Podere Galieni By Interhome - Poggibonsi
Poggibonsi
08/05 – 08/12
$1283/nighttotal: $8981 (7 )

Holiday Home Podere Galieni By Interhome

1 5
house , Certaldo
Holiday Home Podere Galieni by Interhome in Certaldo is located 17 miles from Piazza Matteotti and 24 miles from Piazzale Michelangelo, with the Uffizi Gallery and Piazza della Signoria both 25 miles away.
This spacious 2690 sq ft villa offers 6 bedrooms, 8 bathrooms, a fully equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, terrace, garden, and private parking, accommodating up to 31 guests with 4 complimentary babycots available.
'Eule - Poggibonsi
Poggibonsi
08/08 – 08/15
$145/nighttotal: $1015 (7 )

'Eule

1 2
apartment , Poggibonsi
This terraced house rental is located in Gavignano, Tuscany, 1.24 miles from the nearest town center with shops and services, and 6.21 miles from a lake.
This private ground-floor studio apartment, covering 430 square feet, accommodates 2 guests and features a kitchenette, air conditioning, a private patio with a barbecue and garden, and on-site parking.
Casa Parco Dell'elsa - Poggibonsi
9.0 68 reviews
Poggibonsi
08/07 – 08/09
$154/nighttotal: $308 (2 )

Casa Parco Dell'elsa

1 1
apartment , Colle di Val d'Elsa
Casa Parco dell'Elsa, located in the San Marziale district, offers easy access to Colle di Val d'Elsa and is 15 miles from Siena and its Piazza del Campo.
This 540-square-foot (50-square-meter) one-bedroom, one-bathroom apartment sleeps eight guests and features free WiFi, private parking, a fully equipped kitchen, a fireplace, and is accessible to disabled guests; nearby outdoor activities include golfing, cycling, and hiking.

Frequently Asked Questions about vacation rentals in Poggibonsi

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

    Poggibonsi itself is a charming town with the 13th-century church of San Lucchese and the Museo di Palazzo Pretorio. But just outside of town, you can explore the medieval fortress of Monteriggioni or the historic city of Siena, known for its Piazza del Campo.
  • What are the best Airbnb and vacation rentals in Poggibonsi?

    Vacanze In Toscana Con Piscina, Podere Il Pino and Antica Casa Del Glicine are the most popular Airbnb and vacation rentals in Poggibonsi among travelers.

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

    For walking, the Via Francigena, a historic pilgrimage route, passes through Poggibonsi. For cycling, the Chianti Classico Wine Road is a popular route that takes you through vineyards and picturesque villages. You can also explore the scenic countryside on the Crete Senesi bike path.
  • What are the most popular Airbnbs in Poggibonsi?

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

    There's plenty to do outdoors in the area. You can go hiking in the Crete Senesi, a unique landscape with rolling hills and clay soil. For something more adventurous, try rock climbing at the Parco Naturale Regionale della Maremma. You can also go horseback riding or play golf at the Golf Club Siena.
  • What are the best vacation rentals with a pool in Poggibonsi?

    Vacanze In Toscana Con Piscina, Podere Il Pino and Antica Casa Del Glicine are the best vacation rentals with a pool in Poggibonsi.

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

    Poggibonsi is perfectly located for exploring Tuscany. It's just a short drive to Siena, Florence, and San Gimignano. You can also easily reach the charming towns of Monteriggioni, Colle Val d'Elsa, and Volterra.
  • What are the best rentals for families and kids in Poggibonsi?

    The best rentals for families and kids in Poggibonsi are Vacanze In Toscana Con Piscina, Podere Il Pino and Antica Casa Del Glicine.

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

    Vacation rentals in Poggibonsi usually have basic amenities like a kitchen, bathroom, and bedrooms. Many also offer Wi-Fi, a private patio or garden, and a swimming pool. You can find rentals that are perfect for families, couples, or groups of friends.
  • What are the best rentals or Airbnbs with a jacuzzi in Poggibonsi?

    The best vacation rentals or Airbnb with a jacuzzi in Poggibonsi are Podere Il Pino, Podere Oliveta and Grazioso Appartamento Della Toscana.

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

    The best time to visit Poggibonsi is in the spring or fall when the weather is mild and the crowds are smaller. Summer can be hot and crowded, but you'll have the opportunity to experience the local festivals and events. In the winter, you can enjoy the peace and quiet of the countryside.

Destinations nearby

Best Vacation Rentals with Balconies in Poggibonsi

Enjoy your own private terrace with city skyline views at these vacation rentals in Poggibonsi.

43 M² House ∙ 1 Bedroom ∙ 4 Guests - Poggibonsi
8.7 32 reviews
Poggibonsi
08/08 – 08/15
$132/nighttotal: $924 (7 )

43 M² House ∙ 1 Bedroom ∙ 4 Guests

1 2
house , Poggibonsi
This 460 sq ft terraced apartment in Poggibonsi is located in a quiet district, providing convenient access to local amenities.
This pet-friendly accommodation offers 1 bedroom, 1 bathroom, and can host up to 4 guests, featuring a kitchenette, a terrace, a garden, and WiFi.
Podere Oliveta - Poggibonsi
Poggibonsi
08/08 – 08/15
$324/nighttotal: $2268 (7 )

Podere Oliveta

1 2
house , Poggibonsi
Podere Oliveta, a country house in Poggibonsi, Italy, offers a peaceful countryside setting, conveniently located 22 miles from Siena's Piazza del Campo and Piazza Matteotti, and 26 miles from Florence's Piazzale Michelangelo and Pitti Palace.
This rental features a fully equipped kitchen with a fridge, microwave, and dishwasher; a swimming pool; a terrace; a garden; free Wi-Fi; on-site parking; and one bathroom; perfect for a relaxing Tuscan getaway.
Ladybug Apartment - Poggibonsi
8.6 138 reviews
Poggibonsi
09/20 – 09/22
$69/nighttotal: $138 (2 )

Ladybug Apartment

1 1
apartment , Poggibonsi
The Ladybug Apartment is located in Poggibonsi, just a short drive from Florence's Pitti Palace and Ospedale degli Innocenti. The apartment has excellent ratings for cleanliness, location, and user experience.
The apartment offers 440 square feet of space with one bedroom, one bathroom, and a capacity for two guests. The Ladybug Apartment includes amenities such as a kitchen with a dishwasher and fridge, a terrace with city views, free parking, and free Wi-Fi.
House In A Typical Village In The Heart Of Chianti - Poggibonsi
9.6 57 reviews
Poggibonsi
08/26 – 08/31
$195/nighttotal: $975 (5 )

House In A Typical Village In The Heart Of Chianti

2 1
apartment , Castellina in Chianti
This house is set in a rural area, 2.7 miles from Castello della Paneretta and 3 miles from Isole e Olena Winery. It has excellent user, location, and cleanliness ratings.
The house has 2 bedrooms and 1 bathroom and can accommodate up to 4 guests. It features a fully equipped kitchen, a washing machine, free WiFi, a fenced pool, a garden with barbecue grills, and air conditioning.

Our Favorite Pet-Friendly Vacation Rentals in Poggibonsi

Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Poggibonsi are steps away from dog parks and city walks.

Agriturismo San Gimignano Farmhouse - Poggibonsi
9.5 72 reviews
Poggibonsi
08/05 – 08/12
$2028/nighttotal: $14196 (7 )

Agriturismo San Gimignano Farmhouse

1 5
gîte , San Gimignano
This San Gimignano farmhouse rental is situated in the Tuscan countryside, just 3 miles from the historic center of San Gimignano. The farmhouse features 10 bedrooms and 10 bathrooms, a private swimming pool, tennis court, barbecue area, panoramic veranda, and amphitheater, perfect for large groups or families.
Casa Vacanze Papavero Rosso - Poggibonsi
10 20 reviews
Poggibonsi
06/30 – 07/03
$266/nighttotal: $798 (3 )

Casa Vacanze Papavero Rosso

1 5
apartment , San Gimignano
This Tuscan farmhouse rental, located 3.7 miles from San Gimignano, offers spectacular views of the town's towers and easy access to Siena and Florence.
The three-bedroom, three-bathroom property sleeps six, features a kitchen with a refrigerator, freezer, and dishwasher, a garden, parking, and internet access; nearby Poggibonsi (10 minutes away) provides amenities, train, and bus service, plus bike rentals for exploring the Tuscan countryside.
Reginaserena 2/4 People Private Park - Poggibonsi
10 1 review
Poggibonsi
09/20 – 11/20
$71/nighttotal: $4331 (61 )

Reginaserena 2/4 People Private Park

1 2
apartment , Certaldo
This Certaldo apartment rental is situated in a rural setting, approximately 3 miles from Tenuta Torciano Winery, the SottoVico Garden, and the Museum of Sacred Art.
The 430-square-foot (40-square-meter) unit features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, terrace, garden access, a spa, parking, and free Wi-Fi.
Chianti Villa With Private Park, 2 Apartments & Panoramic Views - Poggibonsi
9.0 1 review
Poggibonsi
08/05 – 08/12
$548/nighttotal: $3836 (7 )

Chianti Villa With Private Park, 2 Apartments & Panoramic Views

6 5
apartment , Poggibonsi
Melachecca apartments in Poggibonsi, Italy offer a convenient base for exploring Tuscany, situated 36 miles from Florence Airport and near local cycling paths.
This two-bedroom rental features a fully equipped kitchen with a fridge and microwave, private parking, a terrace, garden, and a private bathroom with a walk-in shower; bed linens and towels are provided.
©2026 cozycozy.com