Holiday Home Sissi is a self-catering property located in Castel San Gimignano, approximately 40km from Piazza del Campo in San Gimignano and 43km from Piazza Matteotti in Siena, offering easy access to these Tuscan historical centres. This three-bedroom villa boasts three bathrooms, a fully equipped kitchen including a dishwasher and microwave, private parking, a swimming pool, terrace, garden, and free Wi-Fi, comfortably sleeping families or groups.
9.5 1610 reviews
San Gimignano
29/08 – 31/08
£233/nighttotal: £466 (2 )
Tenuta Sovestro - Agriturismo E Winery
1 2
farm , San Gimignano
Tenuta Sovestro, a farmhouse stay near San Gimignano, is conveniently located 35km from both Piazza del Campo and Piazza Matteotti, offering a peaceful retreat yet within easy reach of this Tuscan town and Florence Airport (56km away). This self-catering property features a bedroom, bathroom, and can accommodate two guests, boasting a swimming pool, restaurant, bar, free Wi-Fi, private parking, and a daily continental breakfast; a free shuttle service to San Gimignano is also provided.
9.7 45 reviews
San Gimignano
17/10 – 24/10
£310/nighttotal: £2170 (7 )
Agriturismo L'olmo
5 7
house , San Gimignano
Agriturismo L'Olmo, a family-friendly property with a pool, is located in the Tuscan countryside, 10km from San Gimignano and a 30-minute drive from Monteriggioni. This self-catering house offers a continental breakfast, features a terrace, garden, parking, and all rooms include a TV and private bathroom, making it ideal for exploring Tuscany.
9.2 27 reviews
San Gimignano
06/07 – 19/07
£131/nighttotal: £1703 (13 )
Antica Posta
2 3
house , San Gimignano
Antica Posta is located in the historic centre of San Gimignano, just a minute's walk from the Collegiate Church, offering a peaceful retreat from the bustling tourist crowds. The property has received excellent ratings for its location, cleanliness, and overall experience. This charming two-bedroom house spans 100 square metres and features a fully equipped kitchen, a terrace with stunning views, a garden, and even a tennis court. Guests can enjoy the convenience of free Wi-Fi, parking, and a range of amenities, making it ideal for families and those seeking a comfortable and enjoyable stay in the heart of Tuscany.
8.0 3 reviews
San Gimignano
01/10 – 05/10
£287/nighttotal: £1148 (4 )
Croce Di Bibbiano Apartaments With Pool In Front Of San Gimignano
3 7
house , Colle di Val d'Elsa
This holiday home is located in Poggibonsi, 31 kilometres from Piazza del Campo and 35 kilometres from Piazza Matteotti, with Florence Airport situated 56 kilometres away, offering proximity to San Gimignano. Guests can enjoy amenities including air conditioning, Wi-Fi, a swimming pool, tennis court, garden, and parking, with bicycle rental available for exploring the Tuscan countryside.
10 1 review
San Gimignano
29/08 – 31/08
£148/nighttotal: £296 (2 )
70 M² House ∙ 1 Bedroom ∙ 5 Guests
1 2
house , Certaldo
This one-bedroom house is situated directly on the main square of Certaldo, opposite the Palazzo Pretorio, a significant historical landmark. The 70 square metre property offers a fully equipped kitchen, a spacious living room, a bathroom and a terrace with views of the surrounding Tuscan countryside.
9.3 824 reviews
San Gimignano
19/09 – 24/09
£103/nighttotal: £515 (5 )
Agriturismo Cesani
1 2
farm , San Gimignano
Agriturismo Cesani Vincenzo, a rural retreat 6 kilometres from San Gimignano and 30 kilometres from the Chianti Classico wine region, offers a tranquil Tuscan escape. This family-friendly farmhouse boasts a swimming pool (open June-September), produces its own olive oil, saffron, and wine, and provides vineyard tours and tastings alongside homemade breakfasts served on the terrace. Each room in this property features a private bathroom, LCD satellite TV, and terracotta floors; guests also enjoy free Wi-Fi at reception, air conditioning, and on-site parking.
9.5 47 reviews
San Gimignano
25/08 – 02/09
£129/nighttotal: £1032 (8 )
50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests
1 2
farm , San Gimignano
Farm listing for 2 people with an excellent rating of 95% based on 47 reviews. You will be based in San Gimignano. Facilities and services: a swimming pool, free parking and a fridge. This accommodation in San Gimignano is ideal for families.
8.5 2 reviews
San Gimignano
01/10 – 05/10
£378/nighttotal: £1512 (4 )
Tognazzi Casa Vacanze - Dimora Bunny E Danny
7 7
house , San Gimignano
Tognazzi Casa Vacanze, situated in Villa del Monte, offers a large holiday home approximately 43km from both Piazzale Michelangelo and the Pitti Palace in Florence. This seven-bedroom, seven-bathroom property sleeps 29 guests, boasting a fully equipped kitchen, private parking, Wi-Fi, a jacuzzi, garden, and barbecue facilities; ideal for large groups seeking self-catering accommodation near San Gimignano.
9.9 444 reviews
San Gimignano
20/09 – 25/09
£119/nighttotal: £595 (5 )
Il Palagione
1 2
farm , San Gimignano
Il Palagione farmhouse, near San Gimignano, is situated 10km from the Collegiate Church of San Gimignano and a 20-minute drive from Volterra. This one-bedroom, one-bathroom property sleeps two guests and offers air conditioning, Wi-Fi, a terrace, garden, parking, and a welcome wine tasting.
San Gimignano
15/09 – 21/09
£219/nighttotal: £1314 (6 )
Il Casale Della Gazza Ladra Is A Completely Independent Cottage Located In The Heart Of The Tuscan Countryside, Right In Front Of The Famous Towers Of San Gimignano.
2 2
cottage , San Gimignano
This detached villa, located in the Tuscan countryside near San Gimignano, offers a peaceful retreat amidst organic olive groves and vineyards, with the town centre a mere 5-minute drive away, providing stunning views of the famous towers. The 86 square metre property, accommodating up to four guests in two bedrooms, features a private swimming pool, a garden with a brick courtyard for outdoor dining, and a dedicated study area, all within easy reach of natural attractions like Rocca of Montestaffoli and Alta Val d'Elsa River Park, with private parking provided.
8.2 6 reviews
San Gimignano
01/10 – 05/10
£179/nighttotal: £716 (4 )
120 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 7
house , Certaldo
This detached villa is located in a rural district 2 kilometres from Certaldo, offering countryside views and easy access to local attractions. This 120 square meter villa accommodates up to 8 guests, featuring two distinct living areas with fireplaces, two kitchenettes, a 24 m² terrace with a barbecue, a garden, a swimming pool, and ample 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.
9.2 607 reviews
San Gimignano
15/09 – 21/09
£145/nighttotal: £870 (6 )
Fattoria Abbazia Monte Oliveto
2 2
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.
9.7 12 reviews
San Gimignano
06/07 – 19/07
£153/nighttotal: £1989 (13 )
44 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests
2 3
farm , Colle di Val d'Elsa
Farm rental for 4 guests with an excellent rating of 97% based on 12 reviews. You will be in Colle di Val d'Elsa. Facilities and services: a freeze, a barbecue and a washing machine. This accommodation also has a terrace!
9.4 1918 reviews
San Gimignano
29/08 – 31/08
£457/nighttotal: £914 (2 )
Mormoraia
1 2
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.
9.3 207 reviews
San Gimignano
06/08 – 11/08
£169/nighttotal: £845 (5 )
Borgo Poneta
1 2
farm , Barberino Tavarnelle
Borgo Poneta is a farm stay situated in the Tuscan countryside, just a short drive from the charming towns of Barberino Val d'Elsa and San Gimignano. It has consistently received excellent ratings for its location, cleanliness, and overall experience. This traditional farmhouse offers a taste of authentic Tuscan life with its terracotta floors and panoramic views of the surrounding hills. Guests can enjoy a refreshing dip in the outdoor pool, relax on the terrace, and explore the original wine cellars and a small rural museum.
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
8.8 41 reviews
San Gimignano
06/08 – 11/08
£97/nighttotal: £485 (5 )
Sandra House Certaldo
1 2
house , Certaldo
This detached house is situated in Certaldo, a short distance from the historic centre, approximately 43 kilometres from Florence's Pitti Palace. The property boasts a private pool, free Wi-Fi, and parking, and can comfortably accommodate up to seven guests.
9.3 36 reviews
San Gimignano
07/09 – 12/09
£116/nighttotal: £580 (5 )
Holiday Home L'azalea By Interhome
1 2
house , San Gimignano
Il Poggetto is a charming farmhouse located 7km north of San Gimignano and 4km from Certaldo, offering a peaceful escape in the Tuscan countryside. The property enjoys excellent user, location and cleanliness ratings. The farmhouse offers a range of apartments, each with modern amenities such as air conditioning and free Wi-Fi. Guests can enjoy a communal laundry room, free bike rentals, a playground, a swimming pool, a tennis court, and breathtaking views of the Tuscan countryside.
9.6 99 reviews
San Gimignano
07/09 – 12/09
£138/nighttotal: £690 (5 )
Santa Maria A Poneta
1 2
farm , Barberino Tavarnelle
Santa Maria a Poneta is a working farm situated in the Chianti hills, just 5km from the medieval village of Barberino di Val d'Elsa and 15km from San Gimignano. The farm consistently receives excellent ratings for its location, cleanliness, and overall experience. The farm offers a range of apartments, each with a terrace providing panoramic views of the surrounding countryside. Guests can enjoy a swimming pool, sun loungers, a BBQ area, and a fully equipped kitchen, alongside a host of activities such as wine tasting and exploring the nearby attractions.
8.0 2 reviews
San Gimignano
06/07 – 19/07
£209/nighttotal: £2717 (13 )
Villa Eva
4 3
house , Montaione
This spacious 4-bedroom villa, Villa Eva, is situated in San Vivaldo, approximately 55 kilometres from Pisa International Airport. Offering accommodation for up to 13 guests, this detached property boasts 200 square metres of living space, including a well-equipped kitchen, a living area with a fireplace, a garden with barbecue facilities, and an on-site fitness room.
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 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?
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?
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?
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?
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
9.6 110 reviews
San Gimignano
27/06 – 04/07
£168/nighttotal: £1176 (7 )
Il Borghetto Tuscan Holidays
1 2
house , San Gimignano
Il Borghetto Tuscan Holidays is a country property located 5km outside of San Gimignano, close to Poggibonsi Station and a 45-minute drive from Siena. The property has received excellent ratings for its location, cleanliness, and overall experience. The property offers traditional Tuscan charm with wood-beamed ceilings and traditional furnishings. Guests can enjoy a swimming pool, a restaurant serving Tuscan cuisine, and cooking classes, all while enjoying breathtaking views of the surrounding hills.
9.6 728 reviews
San Gimignano
25/08 – 26/08
£401/nightfor 1 night
Locanda Dei Logi
1 2
farm , San Gimignano
Locanda dei Logi, near San Gimignano, offers adults-only accommodation 42km from Siena's Piazza del Campo and 63km from Florence Airport. This Tuscan farmhouse boasts an infinity pool, a restaurant serving champagne breakfast and dinner, and features allergy-free units with private parking and EV charging, all within a single-bedroom, single-bathroom property.
9.7 3 reviews
San Gimignano
17/10 – 24/10
£352/nighttotal: £2464 (7 )
La Tesa Country House With Pool S. Gimignano
4 7
house , San Gimignano
La Tesa Country House With Pool, near San Gimignano, is situated approximately 37 kilometres from both Piazza Matteotti and Piazza del Campo in Siena. This 150 square metre villa offers four bedrooms, four bathrooms, two living rooms, accommodating up to 15 guests, and boasts a private garden, swimming pool, BBQ, table tennis, and free Wi-Fi.
9.8 39 reviews
San Gimignano
17/10 – 24/10
£336/nighttotal: £2352 (7 )
Nido Del Merlo By Vacavilla
5 7
house , San Gimignano
Nido del Merlo by VacaVilla is situated in Certaldo, 35 kilometres from Piazza Matteotti and 40 kilometres from Piazza del Campo, offering a rural Tuscan retreat. This spacious six-bedroom villa provides 500 square metres of living space, featuring a private balcony, terrace with pool views, an equipped kitchen, barbecue facilities, and an outdoor swimming pool, with cycling and gardening activities available on the property.
Best San Gimignano villas and holiday homes with a garden
8.1 27 reviews
San Gimignano
18/08 – 21/08
£229/nighttotal: £687 (3 )
Villa La Stellina
3 2
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.
San Gimignano
25/07 – 30/07
£371/nighttotal: £1855 (5 )
Sassi Bianchi
3 2
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.
9.5 235 reviews
San Gimignano
15/09 – 21/09
£81/nighttotal: £486 (6 )
Antico Casolare
1 2
farm , San Gimignano
Antico Casolare is a farm stay located just outside the centre of San Gimignano, a short 100-metre walk from the town's main attractions and within 150 metres of the bus stop to Siena. It has excellent ratings for user experience, location and cleanliness. The farm offers a single bedroom and bathroom, with a private entrance and a furnished garden. Guests can enjoy modern amenities such as free Wi-Fi, flat-screen TVs and private bathrooms with free toiletries and hairdryers, as well as participate in the olive and grape harvest, experiencing the farm's agricultural life firsthand.
San Gimignano
27/06 – 04/07
£245/nighttotal: £1715 (7 )
Holiday Home Schönes Ferienhaus Rosanna By Interhome
1 2
house , San Gimignano
This holiday home is located in San Gimignano, approximately 35 kilometres from Florence Airport, 35 kilometres from Piazza Matteotti and Piazza del Campo, and 50 kilometres from Piazzale Michelangelo. This 110 square metre property accommodates up to 9 guests with 1 bedroom and 1 bathroom, featuring a terrace, garden, fireplace, Wi-Fi, and a kitchen equipped with a fridge and dishwasher.