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49 Villa rentals in San Gimignano

Villa Delle Torri - Teloni - San Gimignano
9.5 29 reviews
San Gimignano
8 8
$1825/nighttotal: $20075 (11 )

Villa Delle Torri - Teloni

house - San Gimignano
This villa in San Gimignano is the perfect accommodation for travelers seeking both convenience and tranquility. Just 2 miles from the historic center, it offers a private setting with a garden and barbecue grills for outdoor entertainment.
With excellent user and location ratings, this villa features 8 bathrooms, a fully equipped kitchen, a cozy fireplace, air conditioning, and a swimming pool for exclusive relaxation. It also includes a washing machine for effortless laundry care and a restaurant and room service for added convenience.
Casailcambio - San Gimignano
9.2 201 reviews
San Gimignano
2 1
$91/nightfor 1 night

Casailcambio

house - Colle di Val d'Elsa
CASAILCAMBIO is located in San Marziale, a peaceful neighborhood just 14 miles from Siena's Piazza del Campo and 24 miles from Grosseto's Piazza Matteotti. This rental property has received excellent ratings for its location, cleanliness, and overall experience.
The house has one bedroom and can accommodate up to 3 guests. The property features a private terrace and garden, a well-equipped kitchen, air conditioning, free Wi-Fi, and a fireplace. Guests can enjoy cycling, fishing, and exploring the scenic Tuscan countryside.
Azienda Agricola Fornacelle - San Gimignano
9.6 98 reviews
San Gimignano
2 2
$252/nighttotal: $1512 (6 )

Azienda Agricola Fornacelle

farm - San Gimignano
Country House Tenuta Fornacelle is located in the peaceful Tuscan countryside, just a short drive from the historic town of San Gimignano and the Certaldo Train Station. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house offers a variety of accommodations, including rooms and apartments, each with a private bathroom. Enjoy the outdoor pool, garden, and BBQ facilities, as well as free Wi-Fi, parking, and a shared lounge.
90 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
San Gimignano
4 2
$367/nighttotal: $734 (2 )

90 M² House ∙ 2 Bedrooms ∙ 4 Guests

house - San Gimignano
This San Gimignano vacation home, located 4.3 miles from the medieval town, offers easy access to Tuscany's major cities, Siena and Florence.
The 970-square-foot property features two bedrooms, one bathroom, and accommodates up to four guests, boasting a private garden with a barbecue, shared pool access, and high-speed Wi-Fi.
Il Rosolaccio - San Gimignano
9.4 838 reviews
San Gimignano
2 1
$271/nightfor 1 night

Il Rosolaccio

house - San Gimignano
Il Rosolaccio is a farmhouse located in the Tuscan countryside, a 10-minute drive from the medieval hilltop town of San Gimignano. The house is surrounded by rolling hills, vineyards, and olive groves, offering panoramic views of the Tuscan countryside.
The house has excellent user, location, and cleanliness ratings. It has one bathroom, air conditioning, a swimming pool, a terrace/balcony, a garden, a restaurant, a bar, room service, and parking. The house also offers free Wi-Fi, mini-bars, TVs, and scenic views of the surrounding landscape. Guests can also enjoy characteristic Tuscan dinners served on the terraces, showcasing the local cuisine.
Villa Luisa Design - San Gimignano
9.8 28 reviews
San Gimignano
2 2
$216/nighttotal: $1296 (6 )

Villa Luisa Design

house - Colle di Val d'Elsa
Villa Luisa Design is located in Colle di Val d’Elsa, Tuscany, 19 miles from Siena’s Piazza del Campo and 29 miles from Piazza Matteotti in Siena.
This 1290-square-foot vacation home features two bedrooms, two bathrooms, accommodates nine guests, and boasts a private garden, hot tub, fully equipped kitchen, and free Wi-Fi and parking.
"A Casa Di Franca Villa Con Piscina" - San Gimignano
10 1 review
San Gimignano
13 4
$1314/nighttotal: $2628 (2 )

"A Casa Di Franca Villa Con Piscina"

house - Gambassi Terme
This smoke-free Gambassi Terme villa, located 1.2 miles from Agricola Tamburini Emanuela and within 6 miles of Teatro del Popolo and Palazzo Pretorio, offers a convenient base for exploring Tuscany.
This 2400-square-foot house features four bedrooms, three bathrooms, sleeps twelve guests, includes a private pool, and boasts a fully equipped kitchen with a refrigerator, microwave, and dishwasher.
Tipical Chalet In A Medival Hamlet 3 People - San Gimignano
9.1 183 reviews
San Gimignano
2 2
$139/nighttotal: $417 (3 )

Tipical Chalet In A Medival Hamlet 3 People

house - San Gimignano
This family-friendly apartment rental near San Gimignano, Italy offers a tranquil rural setting, conveniently located within 2 miles of the Castelvecchio Natural Reserve and Castelvecchio, and under 3 miles from the Historical Torture Museum and the Museum of San Gimignano 1300.
The two-bathroom vacation home features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and stovetop, a cozy fireplace, outdoor garden space with barbecue grills, air conditioning, internet access, a tennis court, and parking; pets are welcome.
Entire Big Villa With Private Pool San Gimignano - San Gimignano
San Gimignano
8 7
$1335/nighttotal: $14685 (11 )

Entire Big Villa With Private Pool San Gimignano

house - San Gimignano
This luxurious 3770-square-foot villa is located in a tranquil rural area near San Gimignano, Tuscany, a 19-minute drive from Piazza delle Erbe and the Vernaccia di San Gimignano Wine Museum.
The seven-bedroom, seven-bathroom property comfortably accommodates 14 guests and boasts a private pool, Jacuzzi, spa, and ample parking, along with a fully equipped kitchen and convenient amenities like free WiFi.
Casa I'coco - Appartamento A San Gimignano - San Gimignano
9.9 16 reviews
San Gimignano
2 2
$151/nighttotal: $453 (3 )

Casa I'coco - Appartamento A San Gimignano

house - San Gimignano
Casa I'Coco, a two-bedroom apartment rental in San Gimignano, Italy, is centrally located on Via Berignano 8, offering easy walking access to San Gimignano's major attractions.
This 2-bathroom unit sleeps 3 guests and features a fully equipped kitchen (fridge, freezer, dishwasher), a two-story layout with separate living and sleeping areas, and a washing machine; a portable air conditioning unit is available for summer use.
Borgo Il Castagno - San Gimignano
8.4 23 reviews
San Gimignano
13 5
$748/nighttotal: $1496 (2 )

Borgo Il Castagno

farm - Gambassi Terme
This large estate is situated in the Tuscan countryside, just a short drive from the charming towns of Montaione and San Gimignano. The property has received very good ratings for cleanliness, user experience, and location.
The apartments feature traditional terracotta floors and exposed stone walls, offering a taste of authentic Tuscan living. Guests can enjoy a private patio, a shared barbecue, a swimming pool, and a tennis court, as well as access to a restaurant, a concierge, and free Wi-Fi.
18 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - San Gimignano
9.8 72 reviews
San Gimignano
2 1
$168/nighttotal: $1176 (7 )

18 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm - San Gimignano
Farm listing for up to 2 people with an excellent rating of 98% based on 72 reviews. You will stay in San Gimignano.
Services and facilities include a garden, a barbecue and air conditioning. Take advantage of the pool in this accommodation.

Search Vacation Homes near the Old Town in San Gimignano

Stay close to the action with central vacation homes in San Gimignano, keeping downtown landmarks within easy walking distance.

Casa Nel Centro Storico - San Gimignano
9.2 1 review
San Gimignano
2 1
$298/nightfor 1 night

Casa Nel Centro Storico

house - San Gimignano
This family-friendly house rental in San Gimignano offers a convenient and comfortable stay for travelers seeking a spacious retreat. With a floor area of 650 square feet, the house features a well-equipped kitchen, air conditioning, and a private terrace or balcony, providing ample space and amenities for a relaxing vacation.
The house is conveniently located in San Gimignano, allowing guests to easily explore the town's historic center and surrounding attractions. The house offers free parking, ensuring a hassle-free stay for those traveling by car.
Antico Casolare - San Gimignano
9.6 224 reviews
San Gimignano
2 1
$144/nighttotal: $432 (3 )

Antico Casolare

farm - San Gimignano
Antico Casolare is a family-friendly farm just a 10-minute walk from the heart of San Gimignano, a town famous for its medieval towers and historical charm. The farm has earned excellent ratings for its location, cleanliness, and user experience.
The farm offers rustic-style rooms with private entrances and bathrooms, as well as a garden, free Wi-Fi, and the opportunity to participate in olive and grape harvests. The farm also produces its own olive oil and wine, giving guests a taste of San Gimignano's culinary traditions.
Agriturismo Il Colto - San Gimignano
9.2 275 reviews
San Gimignano
2 1
$115/nighttotal: $230 (2 )

Agriturismo Il Colto

farm - San Gimignano
Agriturismo Il Colto is located just outside the Porta San Giovanni gate of San Gimignano, a short walk from the town walls and a short drive from Poggibonsi and Florence. This farm stay has earned excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers one bedroom and one bathroom, accommodating up to two guests. Enjoy amenities like air conditioning, a terrace, a garden, and free Wi-Fi, along with the unique opportunity to sample and purchase the farm's extra virgin olive oil.
2-grugru House With Private Parking - San Gimignano
10 12 reviews
San Gimignano
2 1
$175/nighttotal: $1225 (7 )

2-grugru House With Private Parking

house - San Gimignano
This apartment is located in San Gimignano's historic district, just a short walk from Piazza della Cisterna, the heart of this UNESCO World Heritage site. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a spacious loft that can accommodate up to four guests. It includes modern amenities like an induction cooktop, a comfortable sofa bed, and a stylish bathroom with unique wallpaper. Guests can also enjoy a private outdoor area where they can relax and soak up the Tuscan sunshine.

Best family friendly San Gimignano villas and beach houses

Among the 49 accommodations in San Gimignano, here are the 4 best family friendly villas and beach houses

Montegonfoli 3 Apartment In San Gimignano X 4+2 - San Gimignano
9.7 295 reviews
San Gimignano
2 3
$169/nighttotal: $507 (3 )

Montegonfoli 3 Apartment In San Gimignano X 4+2

gîte - San Gimignano
This family-friendly farmhouse is located just outside San Gimignano, within a 5-kilometer radius of attractions like Tenuta Torciano Winery, Sant'Agostino Church, and the Archaeological Museum, offering a tranquil escape from the bustling town center. Guests consistently rate this rural retreat excellent for its location, cleanliness, and overall experience.
The farmhouse features a private garden, a swimming pool, and a jacuzzi, perfect for relaxing after a day of exploring the Tuscan countryside. Guests can also enjoy cooking meals in the fully equipped kitchen, grilling outdoors, and staying connected with the complimentary internet access.
Borgo Il Castagno - Villa - San Gimignano
San Gimignano
13 8
$2095/nighttotal: $4190 (2 )

Borgo Il Castagno - Villa

house - Gambassi Terme
This 17th-century Tuscan villa is located in Gambassi Terme, offering panoramic views of the Tuscan hills from an altitude of 500 meters, and is situated just 2 miles from the medieval town of San Gimignano.
This historic estate accommodates up to 20 guests across 8 bedrooms and 8 bathrooms, featuring authentic Tuscan style with terracotta floors and coffered ceilings, a private swimming pool, a garden, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
Villa With Swimming Pool In San Gimignano - San Gimignano
10 4 reviews
San Gimignano
2 4
$1178/nighttotal: $8246 (7 )

Villa With Swimming Pool In San Gimignano

house - San Gimignano
This luxurious villa near San Gimignano, Tuscany, is situated 24 miles from Piazza Matteotti and 26 miles from Siena's Piazza del Campo, offering easy access to these historical landmarks.
The 3,010-square-foot property boasts four bedrooms, four bathrooms, a private pool, a hot tub, a fitness center, and can comfortably accommodate up to 15 guests, making it ideal for large families or groups.
Podere La Quercia - San Gimignano
9.8 304 reviews
San Gimignano
2 2
$380/nighttotal: $760 (2 )

Podere La Quercia

farm - San Gimignano
Podere La Quercia is a recently renovated farmhouse located in the San Gimignano countryside, just 23 miles from the historic center and 26 miles from Siena's Piazza del Campo. This farm stay boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
The farmhouse features comfortable rooms with modern amenities, including air conditioning, free Wi-Fi, and private parking. Guests can enjoy a peaceful garden, a delicious breakfast, and easy access to major Tuscan attractions.

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.

Popular destinations

Best San Gimignano houses with a garden

Borgo Montauto - San Gimignano
9.1 138 reviews
San Gimignano
2 1
$96/nighttotal: $288 (3 )

Borgo Montauto

farm - San Gimignano
This apartment is located in the Tuscan countryside, offering stunning views of San Gimignano and a peaceful escape just a short distance from the historic town center. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The accommodation features a private pool, a terrace, and a garden where you can relax and enjoy the beautiful surroundings. Guests can also take advantage of amenities such as a barbecue, parking, and the option to have breakfast and dinner prepared for them.
Holiday Home Podere Conte Francesco-alvino By Interhome - San Gimignano
9.1 15 reviews
San Gimignano
2 3
$188/nighttotal: $1128 (6 )

Holiday Home Podere Conte Francesco-alvino By Interhome

house - Certaldo
This secluded apartment is located on a vineyard estate with stunning views of the Tuscan countryside. Just outside of Certaldo, this apartment is close to San Gimignano and Florence. With very good user ratings and an excellent location and cleanliness rating, this apartment is a great choice for travelers.
The apartment has four bedrooms, three bathrooms, a full kitchen, a private terrace, a garden, and access to a shared pool. The apartment can accommodate up to six guests and has 1080 square feet of space. The apartment also has Wi-Fi, parking, and is pet-friendly.
L'angolo Fiorito San Gimignano Casa Indipendente - San Gimignano
10 1 review
San Gimignano
2 2
$171/nighttotal: $1197 (7 )

L'angolo Fiorito San Gimignano Casa Indipendente

house - San Gimignano
This independent vacation home is located close to San Gimignano's Duomo and Piazza della Cisterna, offering convenient access to these key local landmarks.
This 970 sq ft rental accommodates up to 7 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchenette, air conditioning, WiFi, a garden, and a terrace.
Le Rose Di Montagnana - San Gimignano
9.2 65 reviews
San Gimignano
2 2
$294/nighttotal: $882 (3 )

Le Rose Di Montagnana

house - San Gimignano
Le Rose di Montagnana is located in San Gimignano, a short distance from the historic center, approximately 22 miles from both Piazza Matteotti and Piazza del Campo.
This 1020 square foot house features two bedrooms, a private pool with a view, a peaceful garden, a fully equipped kitchen, and free private parking.

Best San Gimignano houses with parking

107 M² House ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
San Gimignano
2 2
$519/nighttotal: $1557 (3 )

107 M² House ∙ 2 Bedrooms ∙ 4 Guests

house - San Gimignano
This San Gimignano vacation rental is conveniently located an eight-minute drive from the medieval town center, offering easy access to the historical attractions.
The 620-square-foot apartment sleeps five, features two bedrooms and two bathrooms, a private outdoor area with a pool and terrace, plus free parking, bikes, and on-site food and wine experiences.
Villa Borgo Il Castagno  Historic Villa With Private Pool In The Tuscan Hills - San Gimignano
San Gimignano
13 8
$2117/nighttotal: $4234 (2 )

Villa Borgo Il Castagno Historic Villa With Private Pool In The Tuscan Hills

house - Gambassi Terme
This 17th-century villa, named Borgo il Castagno, is located in Gambassi Terme, Tuscany, approximately 0.3 miles above sea level and 1,640 feet from San Gimignano.
This estate offers 8 bedrooms, 8 bathrooms, and can accommodate up to 20 guests, featuring a private pool, garden, tennis court, and is pet and family-friendly with internet and parking.
Villa Barbarella San Gimignano With  Private Pool - San Gimignano
9.8 9 reviews
San Gimignano
8 5
$1143/nighttotal: $12573 (11 )

Villa Barbarella San Gimignano With Private Pool

house - San Gimignano
This Tuscan villa is located near San Gimignano, a 5-minute drive from the historic center and towers, offering easy access to Siena (40 minutes), Florence (45 minutes), Volterra (25 minutes), and Monteriggioni (30 minutes).
This 5-bedroom, 4-bathroom property sleeps 10, boasts a private pool, tennis court, and ample parking, plus a well-equipped kitchen, and features a separate guest house by the pool.
"A Casa Di Franca" Private Villa In Chianti A Rural Refuge For Families - San Gimignano
10 6 reviews
San Gimignano
13 4
$825/nighttotal: $1650 (2 )

"A Casa Di Franca" Private Villa In Chianti A Rural Refuge For Families

house - Gambassi Terme
This Gambassi Terme villa, near the Benozzo Gozzoli Museum and Teatro del Popolo, offers easy access to the Castle of Oliveto and Palazzo Pretorio.
The 2400-square-foot farmhouse sleeps up to 14 guests, boasting 4 bedrooms, 3 bathrooms, a private pool (open May 15th–October 15th), and amenities including a full kitchen, WiFi, and air conditioning; on-site services like cooking classes and horseback riding are available upon request.

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.

Podere Conte Francesco-alvino - San Gimignano
8.6 9 reviews
San Gimignano
2 3
$180/nighttotal: $1080 (6 )

Podere Conte Francesco-alvino

house - Certaldo
Agriturismo Santa Cristina - San Gimignano
8.9 77 reviews
San Gimignano
2 2
$179/nightfor 1 night

Agriturismo Santa Cristina

farm - Gambassi Terme
Agriturismo Il Castagnolino - San Gimignano
8.4 684 reviews
San Gimignano
2 1
$162/nightfor 1 night

Agriturismo Il Castagnolino

farm - San Gimignano
Oleandro Double Room With Pool In San Gimignano - San Gimignano
9.8 252 reviews
San Gimignano
2 1
$95/nighttotal: $190 (2 )

Oleandro Double Room With Pool In San Gimignano

gîte - San Gimignano

Search 5-Star Holiday Houses in San Gimignano

A well-chosen luxury vacation home in San Gimignano makes the trip. Discover high-end rooms and a location worth the journey.

Casa Vacanze I Borghi - San Gimignano
8.3 12 reviews
San Gimignano
2 1
$155/nighttotal: $1085 (7 )

Casa Vacanze I Borghi

house - San Gimignano

Find the Best Holiday Houses with Jacuzzi in San Gimignano

Coming home to a vacation home with a hot tub after a day in the city changes the whole feel of your San Gimignano getaway.

La Torre Sulla Via Francigena - San Gimignano
9.7 25 reviews
San Gimignano
2 1
$409/nighttotal: $2863 (7 )

La Torre Sulla Via Francigena

farm - Gambassi Terme
Casa Anna "A Lovely Home In Tuscany" - San Gimignano
9.9 106 reviews
San Gimignano
2 3
$180/nighttotal: $1080 (6 )

Casa Anna "A Lovely Home In Tuscany"

house - Colle di Val d'Elsa
Casa Andrea - Maison De Vacances à San Gimignano, - San Gimignano
9.7 19 reviews
San Gimignano
2 2
$223/nighttotal: $6690 (30 )

Casa Andrea - Maison De Vacances à San Gimignano,

house - San Gimignano
Agriturismo Renai E Monte Ii - San Gimignano
9.4 163 reviews
San Gimignano
2 2
$205/nighttotal: $1230 (6 )

Agriturismo Renai E Monte Ii

farm - Gambassi Terme
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