Holiday Rentals in San Gimignano

457 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
San Gimignano holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

457 Holiday rentals and Airbnb in San Gimignano

Best family friendly San Gimignano holiday rentals

Among the 457 accommodations in San Gimignano, here are the 4 best family friendly rentals

Il Borghetto Tuscan Holidays - San Gimignano
9.6 116 reviews

Il Borghetto Tuscan Holidays

house, San Gimignano
Il Borghetto Tuscan Holidays is a country property located 5km outside of San Gimignano, close to Poggibonsi Station and a 45-minute drive from Siena. The property has received excellent ratings for its location, cleanliness, and overall experience.
The property offers traditional Tuscan charm with wood-beamed ceilings and traditional furnishings. Guests can enjoy a swimming pool, a restaurant serving Tuscan cuisine, and cooking classes, all while enjoying breathtaking views of the surrounding hills.
San Gimignano Apartments Chianti - San Gimignano
9.2 155 reviews

San Gimignano Apartments Chianti

apartment, San Gimignano
This centrally located apartment in San Gimignano is just a short distance from both Piazza del Campo in Siena and Piazza Matteotti in Colle di Val d'Elsa, placing you within easy reach of these charming Tuscan towns. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The two-bedroom flat offers 60 square metres of space, comfortably accommodating up to four guests. Amenities include free Wi-Fi, air conditioning, a fully equipped kitchen, a washing machine, and streaming services, ensuring a comfortable and enjoyable stay.
Agriturismo Natura E Salute - San Gimignano
9.1 52 reviews

Agriturismo Natura E Salute

farm, San Gimignano
Agriturismo Natura E Salute is a family-friendly farmhouse near San Gimignano, Tuscany, conveniently located approximately 45km from Siena's Piazza del Campo and 47km from Lucca's Piazza Matteotti.
This self-catering property offers a swimming pool, garden, bar, free Wi-Fi, and free parking, plus activities including table tennis, hiking, biking, and BBQ facilities; a restaurant is open for dinner Thursday-Saturday, and packed lunches are available.
Casa Bardi - San Gimignano
9.7 301 reviews

Casa Bardi

apartment, San Gimignano
Casa Bardi apartments are located in the heart of San Gimignano's historic centre, a UNESCO World Heritage Site, just a short walk from shops, restaurants, and cafes, with Florence being a 50km drive away. The apartments have received excellent ratings for location, cleanliness and user experience.
Each apartment has a private terrace or patio, perfect for enjoying the Tuscan sunshine. Guests can take advantage of the fully equipped kitchenettes, free WiFi, air conditioning, swimming pool, sauna and valet parking, as well as enjoy the beautiful garden.

Best San Gimignano holiday rentals with parking

Casa Renai A San Gimignano (6) - San Gimignano
9.9 26 reviews

Casa Renai A San Gimignano (6)

house, San Gimignano
This charming country house is located just a few kilometres from the historic town of San Gimignano, set amongst the rolling vineyards of the Tuscan countryside. The apartment offers a peaceful escape from the hustle and bustle of city life, with breathtaking views of the surrounding landscape.
This spacious one-bedroom apartment comfortably sleeps three guests, providing a cosy and comfortable stay. The apartment is equipped with a range of amenities, including a swimming pool, a garden, and parking, as well as bicycles available to rent, making it perfect for exploring the local area.
Il Capitello - San Gimignano
9.1 107 reviews

Il Capitello

apartment, San Gimignano
This apartment is located in the historic centre of San Gimignano, just a short walk from the Piazza della Cisterna. It has consistently received excellent reviews for its location, cleanliness and overall experience.
The apartment has one bedroom and one bathroom, covering 50 square metres. It is equipped with a fully fitted kitchen, air conditioning, free Wi-Fi and parking, making it a comfortable and convenient choice for travellers.
Appartamento A San Gimignano - Cipresso - San Gimignano
10 11 reviews

Appartamento A San Gimignano - Cipresso

apartment, San Gimignano
This apartment is located in a peaceful area just a short walk from San Gimignano, offering excellent views of the medieval town and convenient access to Casa Lucii winery, a 2-minute walk away, where guests receive a 25% discount on wine tastings and tours.
This 1-bedroom, 1-bathroom flat accommodates two guests and features a fully equipped kitchen, a private 20 m² terrace with panoramic views, complimentary Wi-Fi, private parking, and access to 'Nà's Garden'.
Appartamento A San Gimignano - Olivo - San Gimignano
10 4 reviews

Appartamento A San Gimignano - Olivo

apartment, San Gimignano
This ground-floor flat offers exceptional panoramic views of San Gimignano from its private garden, located just outside the town's main areas.
This 40 m² apartment accommodates two guests in one bedroom and features a fully equipped kitchen, a bathroom, and an outdoor dining area, ideal for self-catering visitors seeking a Tuscan farmhouse aesthetic.

Frequently asked questions about holiday rentals in San Gimignano

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

    Siena is a beautiful medieval city just 40km away, easily accessible by car or bus. Florence, the capital of Tuscany, is about 60km away and offers a wealth of art, culture, and history. You can also visit the charming hilltop towns of Volterra and Monteriggioni, both within a short drive from San Gimignano.
  • What are the best Airbnb and holiday rentals in San Gimignano?

    Villa Del Sole, Podere Bellavista and Il Casale Del Cotone are among the best Airbnb and holiday rentals in San Gimignano.

  • What amenities are commonly available in vacation rentals in San Gimignano?

    Most vacation rentals in San Gimignano offer basic amenities like kitchens, bathrooms, and bedrooms. Many also have Wi-Fi, air conditioning, and washing machines. You can find rentals with private pools, gardens, and terraces, offering even more comfort and privacy.
  • What are the most popular Airbnbs in San Gimignano?

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

    Spring (April-May) and autumn (September-October) offer pleasant weather and fewer crowds. Summer (June-August) is hot and busy, but the region is beautiful in full bloom. Winter (November-March) can be chilly but offers a quieter and more authentic experience.
  • What are the best holiday rentals with a pool in San Gimignano?

    Villa Del Sole, Podere Bellavista and Il Casale Del Cotone are the best holiday rentals with a pool in San Gimignano.

  • What are the local dishes in San Gimignano region?

    The region is known for its delicious cuisine, including the famous white truffle, which is a must-try in season. Other local specialities include ribollita, a hearty bread soup, pici all'aglione, a pasta dish with garlic and olive oil, and lampredotto, a traditional Florentine street food. Don't forget to sample the local wines, especially the Chianti.
  • What are the best rentals for families and kids in San Gimignano?

    The best rentals for families and kids in San Gimignano are Villa Del Sole, Podere Bellavista and Il Casale Del Cotone.

  • What are the best rentals or Airbnbs with a jacuzzi in San Gimignano?

Popular destinations

Best San Gimignano holiday rentals with a balcony

La Casina Di Ancicucco 2 - San Gimignano
9.0 157 reviews

La Casina Di Ancicucco 2

apartment, San Gimignano
La Casina di Ancicucco 2 is situated just outside the bustling centre of San Gimignano, a peaceful retreat 34 kilometres from Piazza Matteotti and 39 kilometres from Piazza del Campo in Siena. The apartment has received excellent ratings for cleanliness and overall experience, with a very good location rating.
The apartment is a 25 square metre one-bedroom property with one bathroom, comfortably accommodating up to three guests. Guests can enjoy a private garden and terrace, outdoor seating, barbecue facilities, a fully equipped kitchenette, air conditioning, private entrance, and free Wi-Fi and parking.
Casa Alle Allodole - San Gimignano
10 3 reviews

Casa Alle Allodole

apartment, San Gimignano
Casa alle Allodole, a holiday flat in San Gimignano, is situated 40 kilometres from Piazza Matteotti and Piazza del Campo.
This 60 square metre holiday flat accommodates up to seven guests, featuring two bedrooms, one bathroom, a fully equipped kitchen, and a private terrace, with complimentary Wi-Fi and private parking available.
Il Borgo Antico - San Gimignano
9.8 155 reviews

Il Borgo Antico

apartment, San Gimignano
This two-bedroom apartment is situated in the heart of San Gimignano, a short distance from the Piazza delle Erbe and within a 39km radius of Siena's Piazza del Campo and Florence's Piazza Matteotti.
The 68 square metre property comes with a balcony and terrace offering panoramic views of the Tuscan countryside and the town's iconic towers, and boasts a range of amenities including air conditioning, free Wi-Fi, a fully equipped kitchen and private parking.
Casa Matteo San Gimignano Apartments - San Gimignano
8.4 50 reviews

Casa Matteo San Gimignano Apartments

apartment, San Gimignano
Casa Matteo San Gimignano is a one-bedroom flat situated in the historic centre of San Gimignano, just a short walk from the main square, Piazza Cisterna. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The 60 square metre flat comfortably sleeps up to five guests and features a separate living room, a fully equipped kitchen with a dishwasher, a patio, and a garden. Guests can enjoy complimentary wine or champagne, free Wi-Fi, and easy access to public transport to explore the surrounding Tuscan countryside.

Best pet friendly San Gimignano holiday rentals

Among the 457 accommodations in San Gimignano, here are the 4 best pet friendly rentals

Il Pozzo Apartment - San Gimignano
9.5 90 reviews

Il Pozzo Apartment

apartment, San Gimignano
Il Pozzo is a charming apartment situated in the centre of San Gimignano, just 500 metres from the Sant'Agostino Church, offering a peaceful retreat amidst the bustling town. The apartment enjoys excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom apartment spans 60 square metres and comfortably accommodates two guests. Il Pozzo offers a fully equipped kitchen, air conditioning, and free parking, making it an ideal base for exploring the beautiful Tuscan countryside and the nearby city of Florence, just 45 minutes away by car.
The Penthouse Of Dreams - San Gimignano
10 6 reviews

The Penthouse Of Dreams

apartment, San Gimignano
This San Gimignano apartment enjoys an exceptional city-centre location, steps from the Galleria Continua, the Medieval Criminal and Torture Museum, and Piazza della Cisterna.
The two-bedroom, two-bathroom property sleeps four guests and offers free Wi-Fi, a fully equipped kitchen including a dishwasher, and a private balcony with views; on-site parking is also provided, a rare find in the historic centre.
Villa "Arnilù" With Private Pool & Wi-fi - San Gimignano
No reviews

Villa "Arnilù" With Private Pool & Wi-fi

house, San Gimignano
This eight-bedroom villa in San Gimignano is situated within 3km of Sant'Agostino Church, the Archaeological Museum, and the Rocca di Montestaffoli.
The 287 square metre property sleeps sixteen guests and boasts a private pool, garden, ample parking, and a fully equipped kitchen including a dishwasher; free Wi-Fi is also available.
Private Rooms In The Historical Center - San Gimignano
9.2 227 reviews

Private Rooms In The Historical Center

apartment, San Gimignano
This charming bed and breakfast is situated in the heart of San Gimignano, just 200 metres from the Piazza della Cisterna and Piazza del Duomo, along the ancient Via Francigena, offering easy access to the town's main attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The accommodation is housed in a historical medieval building, providing a unique glimpse into San Gimignano's rich past. Guests can enjoy modern amenities like private bathrooms, air conditioning, Wi-Fi, and flat-screen TVs, along with a simple breakfast and information about nearby parking options.
©2026 cozycozy.com