Villas and Holiday homes in San Gimignano

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San Gimignano holiday homes
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49 Villa rentals in San Gimignano

Browse Holiday Homes near the Historic Centre in San Gimignano

Position yourself moments from excellent independent bistros and famous landmarks with central holiday homes in San Gimignano.

La Maison Tour - San Gimignano
9.3 35 reviews

La Maison Tour

house, San Gimignano
This San Gimignano apartment, a self-catering flat in a medieval tower house, is centrally located just 0.5km from the Piazza Duomo.
Sleeping four guests, it features a double and single bed in one bedroom, a sofa bed in the living room, a fully equipped kitchen with washing machine, and a bathroom with bidet; free parking is available 0.47km away.
Casa Simonetta - San Gimignano
9.8 145 reviews

Casa Simonetta

house, San Gimignano
Casa Simonetta is a four-bedroom apartment located 0.8km from San Gimignano's historic centre, offering easy access to the town's attractions.
This self-catering property sleeps seven, features two private parking spaces, secure bicycle storage, free Wi-Fi, a fully equipped kitchen with a fridge-freezer and washing machine, and all linen provided.
Villa La Stellina - San Gimignano
8.5 26 reviews

Villa La Stellina

house, San Gimignano
Villa la Stellina is a self-catering property located just a short distance from the historic centre of San Gimignano, famous for its medieval towers. The property has received very good user ratings, with excellent location and cleanliness scores.
The villa has three bedrooms and covers 100 square metres, providing ample space for families and groups. Guests can enjoy a range of amenities including a swimming pool, terrace, garden, barbecue facilities, and free parking, as well as a fully equipped kitchen with a dishwasher and microwave.
Casa Anna - Appartamento San Gimignano - San Gimignano
10 16 reviews

Casa Anna - Appartamento San Gimignano

house, San Gimignano
Casa Anna, a two-bedroom apartment in San Gimignano, offers convenient private parking and is a short walk from the historic centre.
This recently renovated property sleeps four, boasting two bathrooms, a fully equipped kitchen with dishwasher, air conditioning, and excellent guest reviews.

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

250 M² Villa ∙ 5 Bedrooms ∙ 10 Guests - San Gimignano
No reviews

250 M² Villa ∙ 5 Bedrooms ∙ 10 Guests

house, San Gimignano
This historic Tuscan farmhouse, located in the Chianti region, offers breathtaking views of San Gimignano's iconic towers and is situated 5 kilometres from San Gimignano and 6 kilometres from Certaldo Alto.
This 250 square metre property, ideal for up to 10 guests, features 5 bedrooms and 3 bathrooms, a private pool (open June-September), a garden, parking, and an outdoor dining area with a barbecue, providing a comfortable base for exploring Volterra, Pisa, and Florence.
Torraccia Di Chiusi Agriturismo Relais - San Gimignano
9.7 442 reviews

Torraccia Di Chiusi Agriturismo Relais

farm, San Gimignano
Torraccia di Chiusi Agriturismo Relais is located just outside San Gimignano, a short 2km drive from the medieval town, offering stunning views of the Tuscan countryside. This property has received excellent ratings for location, cleanliness and overall experience.
The farmhouse offers comfortable accommodation in a charming country setting. Guests can enjoy a range of amenities including a swimming pool, spa, restaurant and bar, as well as a terrace and garden.
Agriturismo Casa Alla Madonna - San Gimignano
8.8 31 reviews

Agriturismo Casa Alla Madonna

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.
Appartamenti Tinacci - San Gimignano
9.7 698 reviews

Appartamenti Tinacci

apartment, San Gimignano
Appartamenti Tinacci is located in San Gimignano, just 0.5 kilometres from Piazza Cisterna, the main square of the historic centre. The apartment has excellent user, location and cleanliness ratings, ensuring a pleasant stay.
This self-catering property features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy amenities such as air conditioning, a garden, a spa, and free Wi-Fi, making for a comfortable and enjoyable stay.

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.

Popular destinations

Best San Gimignano villas and holiday homes with a garden

Agriturismo Le Cantine - San Gimignano
9.4 84 reviews

Agriturismo Le Cantine

farm, Poggibonsi
Agriturismo Le Cantine is located in Poggibonsi, just 29 kilometres from the historic centre of Siena and 30 kilometres from the charming Piazza Matteotti. It has received excellent ratings for cleanliness and location, with guests praising its peaceful rural setting.
The farm offers spacious, comfortable accommodation with private patios and river views. Guests can enjoy a range of amenities, including a swimming pool, a restaurant, a garden, and free parking, as well as activities like fishing in the nearby river.
Tenuta Sovestro - Agriturismo E Winery - San Gimignano
No reviews

Tenuta Sovestro - Agriturismo E Winery

farm, San Gimignano
Tenuta Sovestro is a San Gimignano farmhouse offering convenient accommodation within walking distance of the historic centre.
This self-catering property features one bathroom, air conditioning, free Wi-Fi, on-site parking, and a swimming pool; it is unsuitable for large groups.
Casa Mili Cozy 3br With Private Garage - San Gimignano
9.6 149 reviews

Casa Mili Cozy 3br With Private Garage

house, Certaldo
This apartment is conveniently located in Certaldo, just a short walk from the train station and the town centre, with the medieval village of Certaldo Alta a pleasant 1 km away. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes equipped with a modern kitchen, air conditioning, Wi-Fi, and a charming balcony overlooking the town centre, making it ideal for a relaxing and enjoyable stay.
Villa Soffio: A Characteristic And Welcoming Two-story Ancient Tuscan Country House Surrounded By Meadows And By Green Hills, With Free Wi-fi. - San Gimignano
No reviews

Villa Soffio: A Characteristic And Welcoming Two-story Ancient Tuscan Country House Surrounded By Meadows And By Green Hills, With Free Wi-fi.

house, San Gimignano
This spacious San Gimignano villa, sleeping up to 18 guests, is located within 3km of key landmarks including the Sant'Agostino Church, the Archaeological Museum, and the Rocca di Montestaffoli.
The 300 square metre property boasts eight bedrooms, nine bathrooms, a private pool, a garden, and parking, plus a fully equipped kitchen and free Wi-Fi; an on-site games room provides added entertainment.

Best San Gimignano villas and holiday homes with parking

Entire Estate & Villa For 18 People At Tuscan Vineyard Estate With Pool & Bbq - San Gimignano
No reviews

Entire Estate & Villa For 18 People At Tuscan Vineyard Estate With Pool & Bbq

house, Poggibonsi
This exclusive 120-acre private vineyard estate, located in the Tuscan hills 10 minutes by car from Poggibonsi, offers panoramic views of vineyards and olive farms, with proximity to Chianti Classico wineries, San Gimignano (20 km away), Siena (30-45 km away), and Florence (30-45 km away).
This spacious villa comprises five independent apartments and accommodates up to 19 guests with 7 bedrooms and 6 bathrooms, featuring a private swimming pool, BBQ area, pizza oven, bicycle rentals, bocce, ping pong, a children's playground, and complimentary garage parking.
Le Rose Di Montagnana - San Gimignano
9.2 65 reviews

Le Rose Di Montagnana

house, San Gimignano
Le Rose di Montagnana is a two-bedroom house located in San Gimignano, a short 35 km drive from both Piazza Matteotti in Siena and Piazza del Campo, the main square in Siena.
The 95 square metre property offers a private pool, a peaceful garden, free parking and a fully equipped kitchen with a dishwasher, making it ideal for families or groups of friends.
Mormoraia - San Gimignano
9.4 1861 reviews

Mormoraia

farm, San Gimignano
The Mormoraia farm is located in the Tuscan countryside, 4 kilometres outside San Gimignano, a charming medieval town, and a 50-minute drive from both Siena and Florence. The farm has received excellent ratings for its location, cleanliness, and overall experience.
This rural retreat offers a range of accommodation options, including comfortable rooms with handmade terracotta floors. Guests can enjoy a swimming pool, a hot tub, a sauna, a Turkish bath, a restaurant serving traditional Tuscan cuisine, and wine and olive oil tasting sessions.
Sangi Chianti Vacations - San Gimignano
9.4 20 reviews

Sangi Chianti Vacations

house, Poggibonsi
This recently renovated holiday home is located in Poggibonsi, just 45 kilometres from Florence's Pitti Palace and 30 kilometres from Siena's Fontebranda, offering easy access to the region's rich history and culture. The property consistently receives excellent ratings for cleanliness, location and overall user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom property spans 90 square metres and comfortably accommodates up to five guests. The accommodation offers a range of amenities, including a private patio with garden views, a well-equipped kitchen, a garden with barbecue facilities, air conditioning, free Wi-Fi, and private parking.

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.

Tenuta Sovestro - Agriturismo E Winery - San Gimignano
9.5 1541 reviews

Tenuta Sovestro - Agriturismo E Winery

farm, San Gimignano
Holiday Home Podere Conte Francesco-la Palma By Interhome - San Gimignano
8.5 20 reviews

Holiday Home Podere Conte Francesco-la Palma By Interhome

house, Certaldo
Fattoria Di Fugnano - San Gimignano
8.9 52 reviews

Fattoria Di Fugnano

house, San Gimignano
Agriturismo Azienda Agricola La Roccaia - San Gimignano
9.0 365 reviews

Agriturismo Azienda Agricola La Roccaia

farm, San Gimignano

Best Luxury Holiday Homes in San Gimignano

Sophistication and a prime location define each luxury holiday home in San Gimignano.

Casa Gelsomino, Al Centro Dell' Arte E Del Relax - San Gimignano
9.9 48 reviews

Casa Gelsomino, Al Centro Dell' Arte E Del Relax

house, Colle di Val d'Elsa

Explore Holiday Homes with a Hot Tub in San Gimignano

Indulging in a your holiday home with a hot tub at the end of a busy city day in San Gimignano is a wonderful way to switch off.

Villa Iris Luxury San Gimignano, 6 En-suite Bedrooms, Swimming Pool, Spa, Sauna. - San Gimignano
10 122 reviews

Villa Iris Luxury San Gimignano, 6 En-suite Bedrooms, Swimming Pool, Spa, Sauna.

house, San Gimignano
Villa Of 120 Square Meters, Surrounded By A Large Garden, Equipped And Whirlpool Spa - San Gimignano
No reviews

Villa Of 120 Square Meters, Surrounded By A Large Garden, Equipped And Whirlpool Spa

house, Colle di Val d'Elsa
Tenuta Bartoli - San Gimignano
9.9 19 reviews

Tenuta Bartoli

farm, San Gimignano
Villa Con Vista Mozzafiato Torri S.gimignano - San Gimignano
10 8 reviews

Villa Con Vista Mozzafiato Torri S.gimignano

house, San Gimignano
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