Compare villa rentals in San Gimignano from 100+ providers!

31 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
San Gimignano villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

31 Villa rentals in San Gimignano

Check Out Vacation Homes with a Pool in San Gimignano

Choosing a vacation home in San Gimignano with a pool means a private swim is always available.

La Tenuta Di Castelvecchio - San Gimignano
9.1 496 reviews
San Gimignano
10/01 – 10/05
$791/nighttotal: $3164 (4 )

La Tenuta Di Castelvecchio

4 7
farm , San Gimignano
La Tenuta di Castelvecchio is a farm stay near San Gimignano, just 26 miles from both Piazza del Campo and Piazza Matteotti, offering a peaceful escape in the Tuscan countryside. Guests consistently rate this property as excellent for cleanliness and location.
The property features one-bedroom units with private entrances, accommodating up to two guests. Amenities include a swimming pool, a restaurant serving Italian cuisine, and a garden with outdoor play equipment for children.
70 M² House ∙ 1 Bedroom ∙ 4 Guests - San Gimignano
9.4 4 reviews
San Gimignano
08/25 – 08/26
$227/nightfor 1 night

70 M² House ∙ 1 Bedroom ∙ 4 Guests

1 2
house , Certaldo
Sandra House, a 750-square-foot (approximately 70-square-meter) vacation rental in Certaldo, Italy, is conveniently located near Boccaccio's House in Certaldo Alto, with easy access to San Gimignano and Volterra.
This one-bedroom, one-bathroom home offers guests a private garden, swimming pool access, a tennis court nearby, free parking including an EV charging station, high-speed Wi-Fi, a full kitchen with dishwasher, and comfortably sleeps four.
Podere Casanuova - San Gimignano
9.6 73 reviews
San Gimignano
10/01 – 10/05
$886/nighttotal: $3544 (4 )

Podere Casanuova

5 7
farm , San Gimignano
Podere Casanuova is a farm stay located in San Gimignano, Tuscany, just 24 miles from both Siena and San Gimignano, offering a peaceful escape in the Tuscan countryside. The property has excellent user, location, and cleanliness ratings.
Each unit at this farm stay features a fully equipped kitchen and a terrace or patio. Guests can enjoy the outdoor spaces, including a garden, picnic area, and a pool with stunning views of the Tuscan landscape.
Tenuta Sovestro - Agriturismo E Winery - San Gimignano
9.5 1610 reviews
San Gimignano
08/25 – 08/26
$210/nightfor 1 night

Tenuta Sovestro - Agriturismo E Winery

1 2
farm , San Gimignano
Tenuta Sovestro, a farm stay near San Gimignano, Italy, is located 35 kilometers (approximately 22 miles) from Piazza del Campo in San Gimignano and 50 kilometers (approximately 31 miles) from the Pitti Palace in Florence, offering easy access to major Tuscan attractions.
This one-bedroom, one-bathroom guesthouse sleeps two guests and features a swimming pool, terrace, garden, on-site restaurant and bar, free shuttle service, and daily continental breakfast.

Best family friendly San Gimignano villas and beach houses

Among the 31 accommodations in San Gimignano, here are the 4 best family friendly villas and beach houses

54 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
9.4 62 reviews
San Gimignano
06/23 – 07/03
$103/nighttotal: $1030 (10 )

54 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

2 2
farm , Gambassi Terme
Farm listing for up to 4 people with an excellent rating of 94% based on 62 reviews. Your accommodation will be located in Gambassi Terme.
Facilities and services: a kitchen, a fridge and a barbecue. Take advantage of the pool in this accommodation.
Il Balcone Di Rina - San Gimignano
9.8 383 reviews
San Gimignano
06/28 – 06/30
$140/nighttotal: $280 (2 )

Il Balcone Di Rina

1 3
house , San Gimignano
Il Balcone di Rina is located in San Gimignano, a short walk from the town center, approximately 15 miles from Siena's Piazza del Campo.
This one-bedroom vacation rental features a fully equipped kitchen with a dishwasher, a terrace, and a garden, perfect for enjoying the Tuscan weather.
Holiday Home Sissi By Interhome - San Gimignano
9.6 19 reviews
San Gimignano
06/27 – 07/04
$480/nighttotal: $3360 (7 )

Holiday Home Sissi By Interhome

3 2
house , San Gimignano
Holiday Home Sissi is located in Castel San Gimignano, a short drive (approximately 16 miles) from Piazza del Campo in San Gimignano and 17 miles from Piazza Matteotti in Siena.
This three-bedroom vacation rental boasts three bathrooms, a fully equipped kitchen with a dishwasher and microwave, free Wi-Fi, a private terrace, garden, and free parking, comfortably accommodating families or groups.
Sangi Home - San Gimignano
9.0 1 review
San Gimignano
07/25 – 07/30
$522/nighttotal: $2610 (5 )

Sangi Home

2 2
house , San Gimignano
Sangi Home is a pet-friendly vacation rental in San Gimignano, Tuscany, conveniently located a short drive from Piazza Matteotti (24 miles) and Piazza del Campo (27 miles) in Siena.
This 1510-square-foot (approximately 140-square-meter) house features two bedrooms, two bathrooms, and accommodates up to 15 guests, boasting a terrace with city views, a private patio, a fully equipped kitchen with a dishwasher and microwave, and free Wi-Fi.

Frequently Asked Questions about villa rentals in San Gimignano

  • What are the must-see attractions in and around San Gimignano?

    You absolutely can't miss the historic center of San Gimignano, with its iconic towers. The Piazza della Cisterna is a must-visit, and you should also check out the Museo di Arte Sacra. For a day trip, head to Volterra, a charming town with Etruscan roots, or the beautiful medieval town of Siena.
  • 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 hares, foxes, and various bird species. You might even catch a glimpse of a wild boar or a deer if you're lucky. You can also see the famous Chianti vineyards and olive groves in the area.
  • 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?

    Spring (April-May) and fall (September-October) are the best times to visit San Gimignano, as the weather is pleasant and the crowds are smaller. You'll avoid the summer heat and the winter chill.
  • 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 shoulder seasons, like early spring or late fall, are the best times to book a villa rental in San Gimignano. You'll get better rates and have more options to choose from compared to the peak summer months.
  • 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 Sentiero degli Etruschi is a popular hiking trail that winds through the Tuscan countryside, offering stunning views of the rolling hills and vineyards. The trail starts near San Gimignano and leads to Volterra.
  • 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 gives you more privacy and space compared to a hotel. You can enjoy your own private pool, cook your meals in a fully equipped kitchen, and relax in your own outdoor space. You also have the chance to experience the local lifestyle.
  • 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 many popular destinations near San Gimignano. Florence is about an hour away by car, Siena is about 45 minutes away, and Pisa is about an hour and a half away. You can also explore the charming medieval towns of Monteriggioni and Volterra.

Destinations nearby

Best San Gimignano houses with parking

Tre Civette Sul Comò Di San Gimignano - San Gimignano
10 3 reviews
San Gimignano
08/27 – 09/03
$183/nighttotal: $1281 (7 )

Tre Civette Sul Comò Di San Gimignano

2 4
house , San Gimignano
This villa is located in Camporbiano, offering a peaceful retreat a short drive from the historic center of San Gimignano, known for its medieval towers.
This 720 sq ft villa accommodates up to 7 guests with 1 bedroom and 1 bathroom, featuring a private pool, air conditioning, WiFi, a full kitchen, and free private parking.
A Casa Di Nonna - San Gimignano
10 1 review
San Gimignano
08/25 – 08/26
$122/nightfor 1 night

A Casa Di Nonna

1 2
house , Gambassi Terme
A casa di Nonna is a house located in Gambassi Terme, 26 miles from Piazza Matteotti and 27 miles from Piazzale Michelangelo, with Florence Airport 28 miles away.
This family-friendly rental offers 970 square feet of living space with 1 bedroom and 1 bathroom, accommodating up to 11 guests with air conditioning, WiFi, a full kitchen, and private parking.
Agriturismo La Collina Dei Lecci - San Gimignano
9.3 107 reviews
San Gimignano
08/22 – 08/25
$199/nighttotal: $597 (3 )

Agriturismo La Collina Dei Lecci

3 3
farm , San Gimignano
Agriturismo La Collina Dei Lecci is a farmhouse located just 3.7 miles outside of San Gimignano, nestled in the Tuscan countryside amongst vineyards and olive groves, and a short distance from the Castelvecchio Natural Reserve. The farmhouse features antique wood furniture, wood-beamed ceilings, and multiple windows, creating a warm and inviting ambiance, and offers self-catering apartments with fully equipped kitchenettes, dishwashers, and toasters, allowing guests to prepare their own meals and enjoy the local produce.
Papavero Rosso - San Gimignano
9.8 14 reviews
San Gimignano
09/16 – 09/23
$204/nighttotal: $1428 (7 )

Papavero Rosso

3 2
house , San Gimignano
Papavero Rosso, a family-friendly house in San Gimignano, is located approximately 13 miles from Siena's Piazza Matteotti and Piazza del Campo, and 18 miles from Florence's major attractions, offering easy access to Tuscany's highlights. This 1180-square-foot vacation rental boasts three bedrooms, three bathrooms, and can comfortably accommodate up to ten guests, featuring a fully equipped kitchen, garden, free Wi-Fi, and private parking.

Best San Gimignano houses with a garden

Casa Teo - San Gimignano
San Gimignano
09/11 – 09/13
$175/nighttotal: $350 (2 )

Casa Teo

2 4
house , Gambassi Terme
Casa Teo, a 2-bedroom vacation home in Gambassi Terme, is located approximately 24 miles from Piazza Matteotti and 28 miles from Piazzale Michelangelo, offering convenient access to Tuscan landmarks. This 1040 square foot rental accommodates up to 7 guests with air conditioning, a full kitchen, and an outdoor seating area, plus on-site bicycle rentals and sightseeing tours.
Al Piccolo Olivo - San Gimignano
9.7 158 reviews
San Gimignano
07/19 – 07/24
$102/nighttotal: $510 (5 )

Al Piccolo Olivo

1 2
house , Colle di Val d'Elsa
This modern apartment in Colle di Val d'Elsa, Italy, is a 10-minute walk from the historic center and a 2-minute walk from the Via Francigena.
The one-bedroom, one-bathroom rental sleeps four guests and features a combined living/kitchen area, a private garden, air conditioning, free parking, and Wi-Fi.
Agriturismo Macinatico - San Gimignano
9.4 103 reviews
San Gimignano
10/17 – 10/24
$271/nighttotal: $1897 (7 )

Agriturismo Macinatico

3 7
farm , San Gimignano
Agriturismo Macinatico is a farm stay located a short 10-minute drive from the center of San Gimignano, nestled in the Tuscan countryside. The farm consistently receives excellent ratings for location, cleanliness, and overall user experience.
The property offers a variety of accommodations, including rooms with private bathrooms and apartments with kitchens. Guests can enjoy a range of amenities and activities, such as a swimming pool, a tennis court, a garden, and free bike rentals.
Sandra House - Certaldo - San Gimignano
9.0 1 review
San Gimignano
08/25 – 08/26
$213/nightfor 1 night

Sandra House - Certaldo

1 2
house , Certaldo
Sandra House, located in Certaldo, Italy, is approximately 28-30 miles from Florence and its attractions, including the Piazzale Michelangelo and Ponte Vecchio.
This 750-square-foot (approximately 70 square meter) vacation home features one bedroom, one bathroom, and accommodates up to eight guests, offering a private pool, free Wi-Fi, and a fully equipped kitchen with a dishwasher; nearby hiking and cycling trails provide additional recreational opportunities.
©2026 cozycozy.com