Villas and Holiday homes in San Gimignano

49 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
San Gimignano villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

49 Villa rentals in San Gimignano

Best San Gimignano villas and holiday homes with a pool

Among the 49 accommodations in San Gimignano, here are the 4 best villas and holiday homes with a pool

Podere Casanuova - San Gimignano
9.6 58 reviews

Podere Casanuova

farm, San Gimignano
Podere Casanuova is a farm stay located 39km from Piazza del Campo in Siena and 39km from Piazza Matteotti in San Gimignano, offering a peaceful escape in the Tuscan countryside. This accommodation consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The farm stay features a private swimming pool with views of the Tuscan landscape and a fully equipped kitchen in each unit. Guests can enjoy outdoor amenities such as a barbecue area, a picnic area, and a garden, as well as indoor features like a play area for children and free parking.
100 M² House ∙ 3 Bedrooms ∙ 6 Guests - San Gimignano
8.8 13 reviews

100 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Certaldo
This spacious 100m² holiday home is located in the rural outskirts of Certaldo, offering peaceful countryside views and convenient access to local attractions.
This family-friendly property accommodates up to 6 guests, featuring 3 bedrooms, 2 bathrooms, a fully equipped kitchen with a dishwasher and freezer, a private terrace with garden seating and barbecue, and private parking for one dog.
90 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
No reviews

90 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, San Gimignano
La Ripa - Apartment Il Fienile, a 70m² self-catering property, is situated 7km from San Gimignano's centre, offering easy access to both Siena and Florence.
This two-bedroom holiday home sleeps four, boasting a 90m² floor area, a private covered terrace with a wood-fired pizza oven, a shared swimming pool, and high-speed Wi-Fi; on-site parking and bicycle/motorbike storage are also provided.
Podere Conte Francesco-la Palma - San Gimignano
8.0 5 reviews

Podere Conte Francesco-la Palma

house, Certaldo
This semi-detached house is situated on a vineyard estate 7km from Certaldo, 13km from San Gimignano, and 57km from Florence, offering a peaceful countryside retreat near major Tuscan towns.
The 85 square metre property sleeps six, boasting three bedrooms, one bathroom, a private garden with barbecue, a shared seasonal swimming pool (2nd May - 3rd October), and parking; pets are welcome.

Best family friendly San Gimignano villas and holiday home

Among the 49 accommodations in San Gimignano, here are the 4 best family friendly villas and holiday homes

70 M² House ∙ 1 Bedroom ∙ 5 Guests - San Gimignano
10 1 review

70 M² House ∙ 1 Bedroom ∙ 5 Guests

house, Certaldo
This one-bedroom house is situated directly on the main square of Certaldo, opposite the Palazzo Pretorio, a significant historical landmark.
The 70 square metre property offers a fully equipped kitchen, a spacious living room, a bathroom and a terrace with views of the surrounding Tuscan countryside.
Fattoria Di Pancole - San Gimignano
8.9 117 reviews

Fattoria Di Pancole

farm, San Gimignano
Fattoria Di Pancole is situated in the Tuscan countryside, a short five-minute drive from the historic hill town of San Gimignano. The farm enjoys excellent ratings for location, cleanliness, and overall guest experience.
The farm offers spacious apartments with fully equipped kitchens and private gardens, perfect for enjoying the tranquil setting. Guests can relax by the swimming pool, explore the surrounding vineyards and olive groves, or sample the farm's award-winning wines.
Maison Dans La Court Balcon Panoramique Wifi Box - San Gimignano
10 4 reviews

Maison Dans La Court Balcon Panoramique Wifi Box

house, San Gimignano
This San Gimignano apartment, conveniently located in the town centre, offers easy walking access to San Gimignano's main attractions.
The self-catering flat features two double bedrooms, a fully equipped kitchen with dishwasher, a private garden, parking, and can comfortably accommodate four guests.
Villa Angiolino - San Gimignano
10 1 review

Villa Angiolino

farm, Poggibonsi
Villa Angiolino, a semi-detached farmhouse in the Orneto hills near Poggibonsi, is 6km from Poggibonsi, 10km from San Gimignano, and 35km from Siena, offering panoramic views of the Tuscan countryside.
This 200 square metre property sleeps six, boasting three bedrooms, three bathrooms, a fully equipped kitchen with freezer and dishwasher, a private 1000m² garden with outdoor kitchen and barbecue, plus air conditioning and Wi-Fi; cooking courses are available on request.

Frequently asked questions about villa rentals in San Gimignano

  • What are the must-see attractions in and around San Gimignano?

    You absolutely must see the Piazza della Cisterna and the Palazzo Comunale, both in the heart of the historic centre. A short drive outside of San Gimignano, you'll find the beautiful Abbey of San Galgano, with its ruined church and stunning views.
  • What are the best villa rentals in San Gimignano?

    Among the villa rentals in San Gimignano, Villa Del Sole, Podere Bellavista and Il Casale Del Cotone are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of San Gimignano?

    The rolling hills around San Gimignano are great for spotting wildlife. Keep an eye out for wild boar, foxes, and a variety of birds like the hoopoe and the kestrel. You might even be lucky enough to see a deer or two.
  • What are the best villa rentals with a pool in San Gimignano?

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

  • What is the best time to visit San Gimignano?

    Spring (April-May) and autumn (September-October) are the best times to visit San Gimignano. The weather is pleasant, the crowds are smaller, and you can enjoy the beautiful colours of the Tuscan countryside.
  • What are the best villa rentals with a jacuzzi in San Gimignano?

  • When is it easiest to book a villa rental in San Gimignano?

    It's generally easier to book a villa rental outside of the peak tourist season, which is July and August. You'll find better deals and more availability if you book for the shoulder seasons, like April-May or September-October.
  • What are the best villa rentals for families and kids in San Gimignano?

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

  • What are the top hiking trails near San Gimignano?

    There are several great hiking trails in the area. One popular option is the Sentiero degli Etruschi, which follows an ancient Etruscan route. Another is the Via Francigena, a historic pilgrimage route that passes through San Gimignano.
  • What are the best pet friendly villa rentals in San Gimignano?

    The best pet friendly villa rentals in San Gimignano are Il Casale Del Cotone, Antica Dimora and Maggie's Million Dollar View - "Mandarino".

  • What are the advantages of renting a house or a villa in San Gimignano

    Renting a villa gives you more space and privacy compared to a hotel. You can enjoy your own private pool, garden, and outdoor areas. It also offers a more authentic experience of life in the Tuscan countryside.
  • What are the best villa rentals with parking in San Gimignano?

    Villa Del Sole, Podere Bellavista and Il Casale Del Cotone are the best villa rentals with parking in San Gimignano.

  • Are there popular destinations near San Gimignano?

    Definitely! Siena, Florence, and Pisa are all within easy reach of San Gimignano. You can also visit the charming medieval hilltop town of Monteriggioni, which is just a short drive away.

Popular destinations

Best San Gimignano villas and holiday homes with parking

La Ripa - Appartamento Il Fienile - San Gimignano
9.4 202 reviews

La Ripa - Appartamento Il Fienile

house, San Gimignano
La Ripa - Appartamento Padronale is a short distance from San Gimignano's historic centre, making it easy to explore the town's charming streets and iconic towers. The property has received excellent ratings for its location, cleanliness and overall experience.
This two-bedroom house offers comfortable accommodation for families or groups of friends. It has a private patio with garden views, a shared swimming pool, a fully equipped kitchen and free Wi-Fi.
Tenuta Bartoli - San Gimignano
9.9 14 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.
Cielo - Antica Casa Sulla Via Francigena - San Gimignano
9.3 22 reviews

Cielo - Antica Casa Sulla Via Francigena

house, San Gimignano
CIELO - Antica Casa sulla Via Francigena, a house in San Gimignano, is conveniently located near the Via Francigena, approximately 42 kilometres from Siena and its main squares.
This 100 square metre property sleeps up to 9 guests, boasting two bedrooms, two bathrooms, a fully equipped kitchen with oven and microwave, free Wi-Fi, a private garden with barbecue, and free private parking.
Holiday Home Giuggiolo - Giuggioli 1 By Interhome - San Gimignano
9.1 99 reviews

Holiday Home Giuggiolo - Giuggioli 1 By Interhome

house, Poggibonsi
Holiday Home Giuggiolo - Giuggioli 1 by Interhome is located in Bibbiano, a peaceful rural setting just 30km from Siena and a short drive from the charming town of Poggibonsi. The property has received very good ratings for cleanliness, location and user experience.
This one-bedroom house has a private terrace and garden, perfect for enjoying the Tuscan sunshine. The fully equipped kitchen, free Wi-Fi and satellite TV ensure a comfortable and enjoyable stay.

Best San Gimignano villas and holiday homes with a garden

Podere La Quercia - San Gimignano
9.8 308 reviews

Podere La Quercia

farm, San Gimignano
Podere La Quercia is a renovated farmhouse located just 37 kilometres from Piazza Matteotti in San Gimignano and 42 kilometres from Piazza del Campo in Siena, offering a peaceful escape in the Tuscan countryside. This rural retreat has received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers a comfortable stay with a private bathroom, bed linen, and towels in each room. Guests can enjoy a delicious breakfast, relax in the peaceful garden, and benefit from free parking and Wi-Fi access.
53 M² Farmhouse ∙ 2 Bedrooms ∙ 6 Guests - San Gimignano
9.4 62 reviews

53 M² Farmhouse ∙ 2 Bedrooms ∙ 6 Guests

farm, Gambassi Terme
Farm for up to 6 people with an excellent rating of 94% based on 62 reviews. Your accommodation will be located in Gambassi Terme.
Services and facilities include free parking, a barbecue and a dish washer. This accommodation also has a garden!
Montegonfoli 6 San Gimignano Countryside Apt. With Amazing Views And Pool - San Gimignano
No reviews

Montegonfoli 6 San Gimignano Countryside Apt. With Amazing Views And Pool

farm, San Gimignano
This San Gimignano gîte is situated in the Tuscan countryside, just 5 km from the Tenuta Torciano Winery, Sant'Agostino Church, and the Archaeological Museum, Spezieria Santa Fina, and Raffaele De Grada Modern and Contemporary Art Gallery. This 55 square metre property features two bedrooms, two bathrooms, and can accommodate up to four guests, and comes with a private pool, jacuzzi, and a garden with barbecue facilities.
90 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
No reviews

90 M² House ∙ 2 Bedrooms ∙ 4 Guests

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.
©2026 cozycozy.com