Search San Gimignano villas and holiday homes

49 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • 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

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.

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.
Villa Arnilu - San Gimignano
No reviews

Villa Arnilu

house, San Gimignano
Holiday house rental. You will be in San Gimignano.
Services and facilities include a swimming pool, a dish washer and a washing machine. Take advantage of the Free Parking with this accommodation.
Villa ∙ 8 Bedrooms ∙ 20 Guests - San Gimignano
No reviews

Villa ∙ 8 Bedrooms ∙ 20 Guests

house, San Gimignano
Villa Arnilù, a large holiday home near San Gimignano, is situated 2.5km from the medieval town centre, offering easy access to Siena (50km) and Florence (55km).
This eight-bedroom property sleeps up to 20 guests, boasting a private garden with a 6m x 4m swimming pool (open May to October), a summer kitchen, and amenities including Wi-Fi, air conditioning, and a dishwasher; optional cookery courses are available.
Villa Panizzi By Posarellivillas - San Gimignano
9.4 39 reviews

Villa Panizzi By Posarellivillas

house, San Gimignano
Villa Panizzi by PosarelliVillas is located in San Gimignano, just a short distance from the town centre, offering easy access to the historic landmarks. This property has received very good ratings for cleanliness, user experience and location.
This 4-bedroom villa provides ample space for families or groups of friends. Enjoy the Tuscan sunshine and tranquility with a private pool and garden, relax on the balcony with stunning views, and prepare meals in the fully equipped kitchen.

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.

Villa In Le Grazie With 7 Bedrooms Sleeps 14 - San Gimignano
10 14 reviews

Villa In Le Grazie With 7 Bedrooms Sleeps 14

house, Colle di Val d'Elsa
This seven-bedroom villa in Colle di Val d'Elsa is situated within 10km of the Art in Color, the Ranuccio Bianchi Bandinelli Archaeological Museum, and Colle di Val d'Elsa Cathedral.
The 450 square metre property boasts a private pool, a garden with barbecue facilities, and can comfortably accommodate up to 14 guests, offering free WiFi and on-site parking.
Holiday Home Casa Alfredo By Interhome - San Gimignano
8.8 3 reviews

Holiday Home Casa Alfredo By Interhome

house, Colle di Val d'Elsa
Casa Alfredo, in Castel San Gimignano, offers a peaceful retreat approximately 35km from Siena's Piazza del Campo and 66km from Florence Airport.
This 120 square metre property features three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, private parking, Wi-Fi, a swimming pool, and a terrace; ideal for families or groups seeking a relaxing Tuscan getaway.
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
This luxurious villa is located in a peaceful rural setting just outside San Gimignano, within a 5 km radius of the Sant'Agostino Church, the Archaeological Museum, and the Rocca of Montestaffoli.
The 450 square metre property boasts six bedrooms, eight bathrooms, a private pool, a spa, and a fitness centre, comfortably accommodating up to 12 guests.
Casa Francesca In The Countryside Of San Gimignano - San Gimignano
9.9 80 reviews

Casa Francesca In The Countryside Of San Gimignano

house, San Gimignano
Casa Francesca is a renovated hayloft situated in the Tuscan countryside, 2 kilometres from the historic village of Certaldo and a short drive from the medieval town of San Gimignano.
This spacious 3-bedroom apartment, sleeping up to 6 guests, features a fully equipped kitchen, two bathrooms, a large garden, and private 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 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

Borgo Montauto - San Gimignano
9.2 148 reviews

Borgo Montauto

farm, San Gimignano
This charming apartment is situated in the Tuscan countryside, just a short distance from the historic centre of San Gimignano. The property has received excellent ratings for its cleanliness, location and overall experience.
The self-catering apartment features a private swimming pool, a terrace and a garden, perfect for enjoying the warm Tuscan weather. Guests can also enjoy a barbecue, parking on site and the option of breakfast and dinner prepared on request.
Il Poderino - Lussuoso Casolare Di Design - San Gimignano
9.7 103 reviews

Il Poderino - Lussuoso Casolare Di Design

house, San Gimignano
IL PODERINO, a luxurious villa near San Gimignano, is situated approximately 32 kilometres from Piazza del Campo in Siena and 48 kilometres from Florence's Pitti and Strozzi Palaces.
This 140-square-metre property boasts two bedrooms, a fully equipped kitchen with dishwasher, private parking, a swimming pool, and a terrace, comfortably accommodating families or small groups seeking a tranquil garden setting with free Wi-Fi.
La Maison Tour - San Gimignano
9.3 32 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.
Azienda Agricola Polveraia - San Gimignano
9.1 133 reviews

Azienda Agricola Polveraia

farm, San Gimignano
Azienda Agricola Polveraia is located in the Tuscan countryside, just 3 kilometres from the historic town of San Gimignano and a 48 kilometre drive from Volterra. The farm has received very good user ratings and excellent ratings for location and cleanliness.
The property offers a comfortable self-catering apartment with 20 square metres of floor space and a capacity for 2 guests. The farm offers a range of amenities including a garden, a fitness centre, a tennis court, free parking, Wi-Fi, and a delicious breakfast buffet.

Best San Gimignano villas and holiday homes with a garden

Casetta Rustica Nel Chianti - San Gimignano
9.8 29 reviews

Casetta Rustica Nel Chianti

house, Barberino Tavarnelle
Casetta rustica nel Chianti is located in San Donnino, a charming village in the Chianti region, just 21 kilometres from Piazza Matteotti in Florence and 30 kilometres from Pitti Palace. The property has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom cottage offers 55 square metres of space and can accommodate up to four guests. The cottage features a fully equipped kitchen, a cosy fireplace, a private garden, and free Wi-Fi, perfect for relaxing after a day exploring the region.
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.
Vino E Non Solo......... Relax In Chianti - San Gimignano
9.7 26 reviews

Vino E Non Solo......... Relax In Chianti

gîte, Barberino Tavarnelle
This family-friendly holiday home, situated in the Barberino Tavarnelle countryside, is within a few kilometres of the area's main towns and offers stunning panoramic views of the vineyards and olive groves.
Sleeping four guests in two bedrooms and one bathroom, this self-catering property boasts a private swimming pool, barbecue facilities, ample outdoor space, and excellent internet access.
107 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
No reviews

107 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, San Gimignano
This San Gimignano holiday apartment, located 8 minutes' drive (approx. 5km) from the medieval town centre, offers easy access to Tuscany's iconic hilltop town.
The 54-square-metre property boasts two bedrooms, two bathrooms, sleeps five, and includes a private outdoor area with a pool, garden, terrace, barbecue, and outdoor shower, plus access to shared facilities and four parking spaces.

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.

Villa La Stellina - San Gimignano
No reviews

Villa La Stellina

house, San Gimignano
©2026 cozycozy.com