Villas and Holiday homes in San Gimignano

49 available villa offers

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

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.

Casa Nel Centro Storico - San Gimignano
9.2 1 review

Casa Nel Centro Storico

house, San Gimignano
This detached property is located in San Gimignano, offering convenient access to the town's historical sites.
This 60 square meter villa features one bathroom, a kitchen equipped with a fridge, freezer, and microwave, air conditioning, and a terrace, with complimentary Wi-Fi and parking available.
Casa Femi, Panoramic View - San Gimignano
10 21 reviews

Casa Femi, Panoramic View

apartment, San Gimignano
Casa Femi, a spacious 140m² apartment in San Gimignano's historic district, is within easy walking distance of the town's main squares.
This two-bedroom, two-bathroom dwelling sleeps four, boasting a fully equipped kitchen, stunning panoramic terrace, and free Wi-Fi; note that it's on the third floor and lacks lift access.
Maison Historique Et Garage Privé Avec Jardin - San Gimignano
9.6 44 reviews

Maison Historique Et Garage Privé Avec Jardin

house, San Gimignano
This San Gimignano apartment, ideally located in the city centre, is steps from Casa e Torre Campatelli, Rocca di Montestaffoli, and the Ornithological Museum, with the Museum San Gimignano 1300 and Torre Grossa a short 0.4km walk away.
The self-catering flat offers a garden, parking, sleeps four in one bedroom and one bathroom, and includes a fully equipped kitchen with dishwasher, plus a sofa bed and TV.
Casa Maurino - San Gimignano
9.9 131 reviews

Casa Maurino

house, San Gimignano
Casa Maurino is a one-bedroom apartment within San Gimignano's historic city walls, offering a peaceful, central location close to the town's main attractions.
This self-catering flat sleeps two, features a kitchen with fridge, freezer and microwave, air conditioning, a garden, and a panoramic terrace with Tuscan hill views; Wi-Fi is also included.

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

Fattoria Abbazia Monte Oliveto - San Gimignano
9.4 330 reviews

Fattoria Abbazia Monte Oliveto

farm, San Gimignano
Fattoria Abbazia Monte Oliveto is located in the Tuscan countryside, a 47-kilometre drive from Siena and a 2.5-hour drive from the beaches of Marina di Bibbona. This farm stay has received excellent ratings for its location, cleanliness, and overall experience.
The farm offers self-catering apartments with rustic charm and modern amenities. Guests can enjoy a garden with a patio, a swimming pool, BBQ facilities, and the opportunity to sample and purchase local wine and olive oil.
Agriturismo Podere Sertofano - San Gimignano
9.5 582 reviews

Agriturismo Podere Sertofano

farm, Barberino Tavarnelle
Agriturismo Podere Sertofano is situated near Poggibonsi, just 13 kilometres from San Gimignano and 35 kilometres from Siena. This self-catering accommodation offers apartments with equipped kitchens, a shared outdoor pool, and a garden with barbeque facilities, perfect for relaxing and enjoying the Tuscan countryside.
70 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
9.5 46 reviews

70 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, San Gimignano
Accommodation for up to 4 guests with an excellent rating of 95% based on 46 reviews. This accommodation is based in San Gimignano.
Facilities and services include free parking, a dish washer and a garden. Enjoy a swimming pool in this accommodation in San Gimignano!
Agriturismo Fattoria Sant'appiano - San Gimignano
8.9 288 reviews

Agriturismo Fattoria Sant'appiano

farm, Barberino Tavarnelle
Agriturismo Fattoria Sant'Appiano is located in the Chianti wine area, between Florence and Siena, making it a great base for exploring Tuscany. The farm enjoys excellent ratings for location, cleanliness, and overall user experience.
The self-catering apartments are spacious and furnished in a charming Tuscan style. The farm offers a range of amenities, including a swimming pool, a restaurant serving authentic Tuscan cuisine, and the opportunity to purchase farm-fresh produce.

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

Holiday Home Fattoria Di Fugnano-3 By Interhome - San Gimignano
8.7 3 reviews

Holiday Home Fattoria Di Fugnano-3 By Interhome

house, San Gimignano
This holiday home in Libbiano, approximately 42 kilometres from San Gimignano's Piazza della Cisterna and Piazza Matteotti, offers a peaceful countryside escape near the iconic Tuscan town.
The 54-square-metre property features one bedroom, one bathroom, sleeps three guests, and includes a private pool, garden, parking, Wi-Fi, and a fully equipped kitchenette.
Casa Badia - San Gimignano
9.8 223 reviews

Casa Badia

house, San Gimignano
Casa Badia is a charming house situated in Badia, just 39km from the medieval town of San Gimignano and 43km from Florence, offering a peaceful escape from the hustle and bustle of city life. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This three-bedroom house spans 140 square metres and comfortably accommodates up to six guests. Casa Badia offers a range of amenities including a fully equipped kitchen, a terrace, a garden, free parking, and Wi-Fi access, ensuring a relaxing and enjoyable stay.
Podere Il Pino - San Gimignano
8.7 576 reviews

Podere Il Pino

house, Poggibonsi
Podere Il Pino is a holiday home located in the Chianti Hills, just 10km from San Gimignano and a short drive from Colle di Val d'Elsa and Poggibonsi, offering a peaceful retreat in the heart of Tuscany. It has received very good ratings for location, cleanliness and user experience.
Each apartment comes with a private patio overlooking the large garden, providing a relaxing space to enjoy meals and the Tuscan sunshine. Guests can also enjoy the 18-metre pool with hydromassage jets, the small spa, the shared laundry room, and the tennis court.
Agriturismo Il Casolare Di Bucciano - San Gimignano
9.0 1159 reviews

Agriturismo Il Casolare Di Bucciano

farm, San Gimignano
Il Casolare Di Bucciano is a historic farmhouse located 2 kilometres from the Towers of San Gimignano, offering stunning views of the iconic landmark.
This family-friendly accommodation provides 1 bedroom, 1 bathroom, air conditioning, a swimming pool, an on-site restaurant serving local cuisine, and opportunities to purchase farm produce such as Vernaccia and Chianti wines.

Best San Gimignano villas and holiday homes with parking

Farmhouse ∙ 10 Bedrooms ∙ 24 Guests - San Gimignano
No reviews

Farmhouse ∙ 10 Bedrooms ∙ 24 Guests

farm, Colle di Val d'Elsa
Farm rental for up to 24 people. You will be in Colle di Val d'Elsa.
Facilities and services: event friendly rooms, a barbecue and a spa. This accommodation is very convenient for families.
Villa Montecastello - San Gimignano
9.1 145 reviews

Villa Montecastello

farm, Monteriggioni
Villa Montecastello is located in Monteriggioni, just 19 kilometres from San Gimignano and a 30-minute drive from Siena, offering a peaceful retreat in the heart of Tuscany. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
Each apartment features a fully equipped kitchen, allowing guests to enjoy the flexibility of preparing their own meals. The farm also offers a range of amenities and activities, including a swimming pool, a terrace, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.
Podere Galieni - San Gimignano
10 1 review

Podere Galieni

house, Certaldo
Agriturismo 'Podere Galieni' is an elevated property in Certaldo, offering panoramic countryside views and situated 4 kilometres from the town centre, with San Gimignano 15 kilometres, Volterra 30 kilometres, Siena 35 kilometres, and Florence 40 kilometres away.
This spacious 250 square metre holiday cottage, renovated in 2025, accommodates up to 16 guests across 6 bedrooms and 8 bathrooms, featuring air conditioning, WiFi, a private swimming pool (seasonal April-October), and a terraced garden with local farm produce sales.
Casa Renai A San Gimignano (5) - San Gimignano
10 1 review

Casa Renai A San Gimignano (5)

house, San Gimignano
This Tuscan farmhouse apartment, near San Gimignano, is situated a few kilometres from the town centre, amidst Vernaccia vineyards offering easy access to the historic centre.
Sleeping up to five guests, this two-bedroom, one-bathroom dwelling boasts a vintage interior, swimming pool, garden, parking, and on-site amenities including a roulotte-bar and bike rentals.

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.

Entire Estate For 18 People At Tuscan Vineyard - San Gimignano
No reviews

Entire Estate For 18 People At Tuscan Vineyard

house, Poggibonsi
120 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
No reviews

120 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, San Gimignano
Holiday Home Conte Francesco I-3 By Interhome - San Gimignano
8.4 5 reviews

Holiday Home Conte Francesco I-3 By Interhome

house, Certaldo
Borgo Il Castagno - Villa - San Gimignano
No reviews

Borgo Il Castagno - Villa

house, Gambassi Terme

Best Luxury Holiday Homes in San Gimignano

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

Casa Vacanze Etrusco - App Ulivo - San Gimignano
10 1 review

Casa Vacanze Etrusco - App Ulivo

house, San Gimignano

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.

Tognazzi Casa Vacanze - Casa Dante - San Gimignano
No reviews

Tognazzi Casa Vacanze - Casa Dante

house, San Gimignano
Mormoraia - San Gimignano
9.4 1855 reviews

Mormoraia

farm, San Gimignano
Antico Borgo Poggiarello - San Gimignano
9.1 558 reviews

Antico Borgo Poggiarello

house, Monteriggioni
Appartamento Maria - San Gimignano
9.7 12 reviews

Appartamento Maria

farm, San Gimignano
©2026 cozycozy.com