Villas and Holiday homes in San Gimignano

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San Gimignano holiday homes
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31 Villa rentals in San Gimignano

Check Out Holiday Homes with a Pool in San Gimignano

Having pool access at your city holiday home makes a proper swim in the heart of San Gimignano a delightful daily highlight.

Podere Le Grotte - San Gimignano
9.7 122 reviews
San Gimignano
07/09 – 12/09
£90/nighttotal: £450 (5 )

Podere Le Grotte

2 2
house , San Gimignano
Podere Le Grotte is located 4 kilometres outside of San Gimignano, close to the charming town of Certaldo, just a 7.6 kilometre drive away. The property has consistently received excellent ratings for its location, cleanliness and overall experience.
The apartment offers two bedrooms and features a rustic style, allowing guests to experience authentic Tuscan living. Guests can enjoy the beautiful Tuscan countryside with a refreshing dip in the pool, surrounded by the spacious garden and relax on their private terrace.
Montegonfoli 2 Apartment In Countryside Of San Gimignano With Amazing Views 4+2 - San Gimignano
9.6 279 reviews
San Gimignano
27/08 – 03/09
£147/nighttotal: £1029 (7 )

Montegonfoli 2 Apartment In Countryside Of San Gimignano With Amazing Views 4+2

3 4
farm , San Gimignano
This family-friendly farmhouse is situated just outside San Gimignano, within a 5km radius of Tenuta Torciano Winery, Sant'Agostino Church, and the Archaeological Museum, offering a peaceful escape from the town centre. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse has spacious accommodation and outdoor areas perfect for families. Enjoy relaxing evenings in the garden, barbecuing, and swimming in the pool, or unwind in the jacuzzi after a day exploring the local attractions.
Villa Il Vecchio Fienile - San Gimignano
9.6 5 reviews
San Gimignano
29/06 – 03/07
£255/nighttotal: £1020 (4 )

Villa Il Vecchio Fienile

2 2
house , San Gimignano
Villa Il Vecchio Fienile is located just 38 kilometres from Piazza Matteotti in San Gimignano and 40 kilometres from Piazza del Campo in Siena, offering a peaceful escape in the Tuscan countryside. This property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The villa provides spacious accommodation for up to eight guests across two bedrooms and three bathrooms, spanning 150 square metres. Guests can enjoy a private pool, an open-air bath, a barbecue area, a picnic area, and modern amenities such as a satellite flat-screen TV, a fully equipped kitchen, and free Wi-Fi.
Torre Prima Holidays-appartamento Torre 4 - San Gimignano
9.7 41 reviews
San Gimignano
19/07 – 24/07
£80/nighttotal: £400 (5 )

Torre Prima Holidays-appartamento Torre 4

1 2
gîte , San Gimignano
This gîte is located in San Gimignano, within a 5km radius of the Piazza delle Erbe and the Collegiate Church of Santa Maria Assunta.
The property boasts a private garden and a swimming pool, perfect for relaxing after a day exploring the historic centre of San Gimignano.

Best family friendly San Gimignano villas and holiday home

Among the 31 accommodations in San Gimignano, here are the 4 best family friendly villas and holiday homes

52 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
9.5 9 reviews
San Gimignano
22/08 – 25/08
£188/nighttotal: £564 (3 )

52 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

2 3
farm , San Gimignano
Farm listing for up to 4 people with an excellent rating of 95% based on 9 reviews. You will be based in San Gimignano.
Services and facilities include air conditioning, free parking and a washing machine. Take advantage of the garden in this accommodation!
Podere La Quercia - San Gimignano
9.7 537 reviews
San Gimignano
08/07 – 13/07
£173/nighttotal: £865 (5 )

Podere La Quercia

1 2
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.
Agriturismo Sant Ulivieri - San Gimignano
9.5 4 reviews
San Gimignano
30/06 – 07/07
£126/nighttotal: £882 (7 )

Agriturismo Sant Ulivieri

2 5
farm , Colle di Val d'Elsa
Agriturismo Sant Ulivieri, located in Montecchio, is 29 kilometres from Piazza del Campo and 35 kilometres from Piazza Matteotti, offering a farm stay near Colle di Val d'Elsa.
This agriturismo provides accommodations with kitchens, garden views, and private patios, alongside on-site dining, complimentary WiFi, and free parking, with Florence Airport being 56 kilometres away.
Podere Casanuova - San Gimignano
9.6 73 reviews
San Gimignano
30/06 – 07/07
£588/nighttotal: £4116 (7 )

Podere Casanuova

4 5
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.

Frequently asked questions about villa rentals in San Gimignano

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

    You absolutely must visit the Piazza della Cisterna, a beautiful square with a well in the centre. Don't miss the Torre Grossa, the tallest of the remaining towers, and the Museo di Arte Sacra, which houses a collection of religious art. Just outside of San Gimignano, you can find the Abbey of San Galgano, a stunning ruined abbey with a fascinating history.
  • What are the best holiday homes in San Gimignano?

    Among the holiday homes 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?

    You'll likely see lots of birds, like sparrows and larks, and maybe some squirrels in the trees. If you're lucky, you might spot a fox or a weasel in the countryside. There are also some lovely vineyards and olive groves nearby.
  • What are the best holiday homes with a pool in San Gimignano?

    Villa Del Sole, Podere Bellavista and Il Casale Del Cotone are the best holiday homes 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 the colours of the Tuscan countryside are at their most vibrant.
  • What are the best holiday homes with a jacuzzi in San Gimignano?

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

    Booking outside of peak season, like in the shoulder months of April-May or September-October, will give you the best chance of finding a good deal and availability. You can also try booking last minute if you're flexible with your dates.
  • What are the best holiday homes for families and kids in San Gimignano?

    The best holiday homes 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?

    The Sentiero degli Etruschi is a great hiking trail that passes through vineyards and olive groves, offering stunning views of the Tuscan countryside. There's also the Via Francigena, a historic pilgrimage route that passes through San Gimignano, with plenty of opportunities for scenic walks.
  • What are the best pet friendly holiday homes in San Gimignano?

    The best pet friendly holiday homes 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 than a hotel, and you can enjoy the feeling of being at home in a beautiful setting. You'll also have access to a kitchen, so you can prepare your own meals and save money on dining out.
  • What are the best holiday homes with parking in San Gimignano?

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

  • Are there popular destinations near San Gimignano?

    Yes, there are plenty of popular destinations near San Gimignano. Siena, Florence, and Pisa are all within easy reach by car or train, and each offers its own unique attractions and experiences.

Destinations nearby

Best San Gimignano villas and holiday homes with parking

Il Fienile Di Pescille - San Gimignano - San Gimignano
9.0 7 reviews
San Gimignano
15/09 – 21/09
£669/nighttotal: £4014 (6 )

Il Fienile Di Pescille - San Gimignano

3 2
house , San Gimignano
Il Fienile di Pescille, near San Gimignano, is situated approximately 40 kilometres from both Piazza Matteotti in Siena and Piazza del Campo, offering easy access to these Tuscan landmarks.
This three-bedroom villa boasts 200 square metres of floor space, sleeps up to 11 guests, and features a private pool, tennis court, and fully equipped kitchen; nearby cycling routes explore the Tuscan countryside.
Antica Dimora - San Gimignano
9.5 769 reviews
San Gimignano
11/09 – 13/09
£238/nighttotal: £476 (2 )

Antica Dimora

1 2
house , San Gimignano
Antica Dimora is a charming house situated in a medieval village just 4 kilometres from San Gimignano, offering a peaceful retreat in the Tuscan countryside. The property has received excellent ratings for its location, cleanliness and overall experience.
The house is furnished with antiques and features four-poster beds, creating a traditional Tuscan ambiance. Guests can enjoy amenities such as a fully equipped kitchen, a terrace, a garden, and free Wi-Fi access.
Sassi Bianchi - San Gimignano
San Gimignano
27/08 – 03/09
£201/nighttotal: £1407 (7 )

Sassi Bianchi

2 4
farm , San Gimignano
Sassi Bianchi farmhouse, in the Chianti hills, offers self-catering accommodation 2.5km from San Gimignano and within easy reach of Volterra and Colle di Val d'Elsa.
This restored 16th-century farmhouse provides guests with a swimming pool, tennis court, bocce ball court, and optional cooking classes, alongside features including a fridge, freezer, microwave, dishwasher, air conditioning, and private terraces with BBQs.
Casa Anna "A Lovely Home In Tuscany" - San Gimignano
9.9 107 reviews
San Gimignano
27/08 – 03/09
£200/nighttotal: £1400 (7 )

Casa Anna "A Lovely Home In Tuscany"

3 4
house , Colle di Val d'Elsa
Casa Anna is located in the historic district of Colle di Val d'Elsa, a short walk from the charming Piazza Arnolfo and the Duomo, offering a peaceful retreat in the heart of this Tuscan town. The house has consistently received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
This three-bedroom, two-bathroom property features a spacious terrace with stunning views of the Tuscan countryside. Casa Anna offers a range of amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families and groups looking for a relaxing and active holiday.

Best San Gimignano villas and holiday homes with a garden

Agriturismo Podere Cappella - San Gimignano
8.3 207 reviews
San Gimignano
25/07 – 30/07
£60/nighttotal: £300 (5 )

Agriturismo Podere Cappella

1 2
farm , San Gimignano
Agriturismo Podere Cappella is a 2km drive from the historic centre of San Gimignano, nestled in the rolling hills of the Tuscan countryside. The farm receives excellent ratings for location, cleanliness, and overall experience.
The property offers a 1-bedroom apartment with a floor area of 17 square metres, suitable for 2 guests. Amenities include a terrace, garden, free parking, and Wi-Fi, as well as the opportunity to sample the farm's own wine and fruit.
Conte Francesco Ii - San Gimignano
8.0 3 reviews
San Gimignano
30/06 – 07/07
£192/nighttotal: £1344 (7 )

Conte Francesco Ii

4 5
house , Certaldo
This four-bedroom house, situated on a vineyard estate 7km from Certaldo, enjoys a secluded location offering stunning countryside views and easy access to San Gimignano (13km), Florence (57km), Siena (45km), and Volterra (40km).
The 120 square metre property features two kitchens, two bathrooms, two terraces with barbecue facilities, a private garden, parking, a shared seasonal swimming pool (May 2nd - October 3rd), and accommodates up to eight guests, including pets.
Villa Boccaccio - San Gimignano
San Gimignano
27/07 – 30/07
£767/nighttotal: £2301 (3 )

Villa Boccaccio

6 6
house , San Gimignano
This non-smoking villa is located in San Gimignano, 19.3 kilometres from Casa Boccaccio and 19.3 kilometres from Tenuta Torciano winery, offering an ideal base for exploring the region with nearby birdwatching and cycling opportunities.
The 350 square metre property accommodates up to 12 guests across six bedrooms and four bathrooms, featuring a well-equipped kitchen, air conditioning, a Jacuzzi, a terrace, and a garden.
Fattoria Di Fugnano Winery - San Gimignano
9.5 144 reviews
San Gimignano
07/09 – 11/09
£81/nighttotal: £324 (4 )

Fattoria Di Fugnano Winery

4 2
gîte , San Gimignano
This Tuscan countryside self-catering apartment near San Gimignano offers a private pool and garden, conveniently located for exploring Siena and Florence (distances unspecified).
The 55 square metre property comprises a living room, bedroom, bathroom, and sleeps two, with an option for extra beds, plus wine tasting and multiple apartments available for larger groups.
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