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San Gimignano villas
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49 Villa rentals in San Gimignano

Find the Best Holiday Homes with a Swimming Pool in San Gimignano, Italy

Enjoy an exclusive swim in total privacy right in your own backyard at houses featuring a swimming pool in San Gimignano, Italy.

Fattoria Di Pancole - San Gimignano
8.9 114 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.
Montegonfoli 4, Apartment For 4 Adults With Amazing Views On San Gimignano - San Gimignano
9.6 135 reviews

Montegonfoli 4, Apartment For 4 Adults With Amazing Views On San Gimignano

apartment, San Gimignano
This charming gîte is located just 5km from San Gimignano, in a peaceful rural setting close to Tenuta Torciano Winery, Sant'Agostino Church, and the Archaeological Museum. It has received excellent ratings for location, cleanliness, and overall experience.
The 80 square metre property sleeps up to 5 guests and offers two bedrooms and two bathrooms. Enjoy a range of amenities including a private swimming pool, jacuzzi, terrace, garden, and barbecue facilities.
Il Fienile Di Pescille - San Gimignano - San Gimignano
8.9 9 reviews

Il Fienile Di Pescille - San Gimignano

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.
Casa Vacanza Le Case - San Gimignano
9.1 974 reviews

Casa Vacanza Le Case

house, San Gimignano
Casa Vacanze Le Case is situated in the Tuscan countryside, 3.5 kilometres from the centre of San Gimignano and 16 kilometres from Poggibonsi, offering a peaceful escape from the bustling town. This property has received excellent ratings for its cleanliness, location and overall experience.
The house boasts a rustic charm with vaulted ceilings and a private outdoor pool for relaxing on hot summer days. Guests can enjoy al fresco dining with BBQ facilities, a sun terrace and a garden, as well as free WiFi and parking.

Top Family-Friendly Villas in San Gimignano, Italy

Share home-cooked meals and enjoy plenty of room for all ages inside family houses in San Gimignano, Italy.

Fattoria Abbazia Monte Oliveto - San Gimignano
9.3 333 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 Casa Alla Madonna - San Gimignano
8.8 35 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.
Casa Renai A San Gimignano (3) - San Gimignano
9.9 26 reviews

Casa Renai A San Gimignano (3)

house, San Gimignano
This Tuscan farmhouse apartment is situated a few kilometres from the centre of San Gimignano, amidst Vernaccia vineyards.
The self-catering property offers one bedroom, one bathroom, sleeps two guests, and boasts a private outdoor area, swimming pool, and on-site roulotte-bar, plus optional meals and bike rentals.
Capanna Frui Ruris, Relax Nella Campagna Toscana - San Gimignano
No reviews

Capanna Frui Ruris, Relax Nella Campagna Toscana

house, San Gimignano
This Tuscan villa is situated in San Gimignano, approximately 37 kilometres from Piazza Matteotti and between 43 and 47 kilometres from Florence's Piazzale Michelangelo, the Uffizi Gallery, and Ponte Vecchio.
This pet-friendly house accommodates up to seven guests across two bedrooms and two bathrooms, offering air conditioning, a fully equipped kitchen, and complimentary WiFi, with private parking available.

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 stunning square with a well and a beautiful view of the surrounding Tuscan countryside. The Torre Grossa, a 54-metre tall tower, offers a panoramic view of the city. And don't miss the Museo di Arte Sacra, which has a collection of 13th to 16th century art.
  • 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 countryside around San Gimignano is home to a variety of wildlife, including wild boar, deer, foxes, and hares. You might also spot birds of prey like buzzards and kestrels, and if you're lucky, you might even see a wild cat.
  • 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?

    The best time to visit San Gimignano is during the shoulder seasons, from April to May or September to October. The weather is still pleasant, and the crowds are smaller. You'll also find a good selection of local produce at the markets.
  • What are the best villa rentals with a jacuzzi in San Gimignano?

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

    The easiest time to book a villa rental in San Gimignano is during the off-season, from November to March. You'll find the best deals and have a wider selection of properties to choose from.
  • 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?

    The Via Francigena is a popular hiking trail that passes through San Gimignano. You can also hike up to the nearby town of Certaldo, which is home to the house where Giovanni Boccaccio was born. There are also several shorter trails in the surrounding countryside.
  • 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 in San Gimignano gives you more space and privacy than staying in a hotel. It also allows you to experience the local lifestyle, as you have access to a kitchen and can cook your own meals. You can also enjoy the peace and quiet of 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?

    Yes, there are several popular destinations near San Gimignano. Siena, Florence, and Pisa are all within easy reach, and offer a variety of attractions, from historical sites to art museums to shopping.

Popular destinations

Best San Gimignano villas and holiday homes with parking

Casa Tibesa By Interhome - San Gimignano
9.0 2 reviews

Casa Tibesa By Interhome

house, San Gimignano
This 70m² apartment in Borgo Roccaia, 6km from San Gimignano's historic centre, offers stunning panoramic views of the Tuscan countryside.
The two-bedroom, one-bathroom property sleeps four, and includes a fully equipped kitchen with dishwasher, private terrace, shared seasonal swimming pool, garden, parking, and WiFi; a cot and highchair are also provided.
Fattoria Di Mugnano - San Gimignano
9.0 283 reviews

Fattoria Di Mugnano

farm, Colle di Val d'Elsa
Fattoria di Mugnano is a working farm situated in the Tuscan countryside, 6 kilometres from Colle di Val d'Elsa and close to the ancient Via Francigena pilgrimage route.
This 15 square metre property offers a single bedroom with a private bathroom, a shared living room, and a terrace, allowing guests to enjoy the stunning views of the surrounding vineyards and the Tuscan countryside.
Villa Sabrina By Posarellivillas - San Gimignano
10 124 reviews

Villa Sabrina By Posarellivillas

house, San Gimignano
Villa Sabrina by PosarelliVillas is situated just a short distance from the centre of San Gimignano, offering easy access to the charming medieval streets and towers. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The villa features three bedrooms and two bathrooms, providing ample space for families or groups, and spans 160 square metres. Guests can enjoy the private pool and garden, dine al fresco on the patio, and make use of the barbecue facilities, while the fully equipped kitchen, satellite TV, and free Wi-Fi ensure a comfortable stay.
Casa Andrea By Posarellivillas - San Gimignano
9.7 3 reviews

Casa Andrea By Posarellivillas

house, San Gimignano
Casa Andrea, a family-friendly property, is situated 40 kilometres from Siena’s Piazza del Campo and Piazza Matteotti, offering a peaceful retreat in the Tuscan countryside.
This 80-square-metre house boasts two bedrooms, two bathrooms, and can comfortably accommodate seven guests, featuring a fully equipped kitchen with a dishwasher, air conditioning, a garden, parking, and Wi-Fi; note that the hot tub is currently closed for maintenance until 1 April 2025.

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 Titta, La Toscana Intorno A Te - San Gimignano
9.8 34 reviews

Casa Titta, La Toscana Intorno A Te

house, San Gimignano
CasaTitta, a three-bedroom apartment in the San Gimignano countryside, offers exceptional views of the Tuscan landscape, though its precise distance from the town's historical centre requires further clarification.
This family-friendly dwelling sleeps five, boasting a fully equipped kitchen, swimming pool, parking, and internet access; its blend of antique and modern furnishings creates a unique interior within a comfortable layout.
Ripabella - San Gimignano
9.3 103 reviews

Ripabella

house, San Gimignano
This adults-only villa near San Gimignano, in the Ripabella district, is situated approximately 34km from Piazza Matteotti and 39km from Piazza del Campo in Siena.
The self-catering property boasts a private pool with Tuscan countryside views, a jacuzzi, fitness centre, one bedroom, one bathroom, sleeping two guests, and features a fully equipped kitchen, terrace, garden, and free Wi-Fi and parking.
Podere Bellavista - San Gimignano
9.7 741 reviews

Podere Bellavista

house, San Gimignano
Bellavista, a renovated country house, sits 5km from San Gimignano's historic centre, offering stunning views from its hilltop location amidst vineyards and olive groves.
This one-bedroom, one-bathroom property boasts a swimming pool, terrace, garden, and on-site restaurant and bar, providing Wi-Fi, air conditioning, parking, and room service for a relaxing stay.

Select the Best High-End Houses in San Gimignano, Italy

Treat yourself to high-end design, custom furniture, and premium finishes at luxury small-city houses in San Gimignano, Italy.

80 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
No reviews

80 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, San Gimignano
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