San Gimignano vacation rentals

We found 3,354 vacation rentals — enter your dates for availability

Select from 65 houses, 250 apartments, and other vacation rentals to find the perfect place for your stay in San Gimignano. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you expect for your stay, such as parking and air conditioning. No matter what you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - San Gimignano

Showing deals for:Feb 6 - Feb 13
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about San Gimignano

Why visit San Gimignano

  • Rich Historical Heritage: San Gimignano is renowned for its medieval architecture, churches, and museums that embody its fascinating history.
  • Romantic Atmosphere: The charming streets and stunning views create an enchanting setting perfect for couples and romantic getaways.
  • Scenic Chianti Hills: Explore the picturesque landscapes of the Chianti region, offering breathtaking vistas and serene surroundings.
  • Diverse Accommodation Options: Choose from a variety of vacation rentals, including villas, apartments, and private homes for a comfortable stay.
  • Welcoming Local Culture: Experience the warmth of friendly locals and immerse yourself in the authentic Italian lifestyle.

Popular types of accommodation in San Gimignano

If you're wondering about accommodation options in the charming town of San Gimignano, we've got you covered. The most sought-after choices for vacation rentals include apartments, houses, and stunning villas. Whether you're looking for a villa rental, holiday rental house, or a convenient stay, our selection of villa rentals in Italy ensures you'll find the perfect getaway to enjoy this picturesque destination.

  • Apartments: The top choice for visitors in San Gimignano, offering convenient and comfortable living spaces ideal for both short and long stays.
  • Houses: A popular option for families and groups, these homes provide a homey atmosphere with all the amenities needed for a pleasant getaway.
  • Villas: Experience luxury and spaciousness in these elegant properties, perfect for a memorable vacation surrounded by stunning landscapes.
  • Caravan Parks: For those seeking a unique outdoor experience, caravan parks offer a blend of adventure and comfort, with facilities for camping enthusiasts.
  • Cottages: Embrace a quaint and charming stay in these cozy retreats, ideal for couples or solo travelers looking for relaxation.**

Top attractions in San Gimignano

San Gimignano is perfect for those seeking a cultural, romantic, or outdoor getaway. Visitors can explore captivating sites like churches, museums, and castles, making it an ideal destination for those interested in rich history and enchanting experiences. Whether you're wandering through charming streets or enjoying stunning views, San Gimignano offers a delightful blend of culture and romance that will make your vacation truly unforgettable.

  • San Gimignano Communal Palace: This historic Civic Government Building offers a glimpse into the rich history of San Gimignano, featuring stunning architecture and cultural exhibits that reflect the town's medieval past.
  • Piazza della Cisterna: A picturesque square surrounded by charming medieval buildings, it’s the perfect spot to soak in local culture, enjoy gelato, and admire the vibrant atmosphere.
  • Medieval Criminal and Torture Museum: Delve into the darker aspects of history at this intriguing museum, showcasing medieval justice practices and torture devices, providing a unique perspective on the past.

Things to do recommended for couples

Planning a romantic getaway in San Gimignano? Enjoy a delightful wine tasting at Tenuta Torciano Winery or Sovestro in Poggio Winery, both exuding charm. For a lovely meal, head to Torre del Porcellino, just 16.1km away, where the ambiance is perfect for couples.

Things to do recommended for families

In San Gimignano, families can experience the sports excitement at Palasport Mens Sana, relax in the serene Alta Val d'Elsa River Park, and explore the wonders of the Chianti Observatory, perfect for an entertaining day out with kids.

Things to do recommended for groups

Your group can enjoy the scenic Sentierelsa Trail for hiking, visit the enchanting Teatro del Silenzio for a cultural experience, and tee off at the picturesque Castelfalfi Golf Course. Each activity offers a unique blend of adventure, entertainment, and outdoor fun, perfect for creating lasting memories together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in San Gimignano

When planning your trip, whether it's with a group, your family, or even your pets, and if you’re considering extended stays, be sure to apply the appropriate filters to align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to San Gimignano with a group: Think about how many bedrooms you'll require, as well as any additional features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to San Gimignano with young kids: Travelling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with having access to suitable amenities, like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to San Gimignano: For many, a family getaway isn’t truly complete without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting San Gimignano: If you're searching for vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rental options. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in San Gimignano

Your vacation in San Gimignano, Tuscany promises a delightful blend of culture and relaxation. This charming city, known for its historical architecture, offers a romantic atmosphere amid the picturesque Chianti Hills. Venture beyond to discover tranquil holiday homes and friendly locals, ensuring a serene getaway. Explore the surrounding regions for a taste of luxury and secluded beauty that encapsulates the essence of a perfect Italian holiday.

  • San Gimignano City Centre: The San Gimignano City Centre is a vibrant hub that captures the essence of Tuscan culture. Nestled within the historic walls of San Gimignano, this neighborhood offers a delightful blend of outdoor activities, family-friendly experiences, and rich cultural exploration. Visitors can enjoy relaxing in local spas, taking in performances at quaint theatres, or wandering through the charming streets filled with historic sites and tourist precincts. Highlights include the iconic towers that define the skyline and the picturesque piazzas that are perfect for soaking in the atmosphere of this medieval town.
  • Castel San Gimignano: Castel San Gimignano is a quaint village that enchants visitors with its romantic charm and cultural heritage. Located just a short distance from San Gimignano, this village is ideal for those looking to immerse themselves in history while enjoying entertainment-themed experiences. Popular activities include guided tours that explore the area’s rich history and scenic walking paths that reveal stunning views of the surrounding landscape. Key attractions include a historic civic government building, a charming piazza, and an elegant historic palace, making it a perfect destination for a leisurely day trip.
  • Ulignano: Ulignano is a serene village known for its romantic ambiance and outdoor activities. Situated in close proximity to San Gimignano, this village invites visitors to indulge in body treatments at local wellness centres and enjoy outdoor theatre performances. The area boasts beautiful piazzas, historic places, and quaint historic houses that add to its charm. Whether you are looking to relax or explore, Ulignano offers a peaceful retreat with plenty of opportunities to connect with nature and experience the beauty of Italian village life.

Best time to go to San Gimignano

If you're planning a trip to San Gimignano, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and November, while off-peak times, like January to February and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
February43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low
March48.4°F (9.1°C)Light RainMostly SunnyAverageSlightly Low
April54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
May61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
June70.7°F (21.5°C)Light RainSunnySlightly HighSlightly High
July76.3°F (24.6°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.9°F (24.4°C)No Rain (Dry)SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October59.0°F (15.0°C)Light RainMostly SunnySlightly LowAverage
November50.4°F (10.2°C)Light RainMostly SunnySlightly HighAverage
December43.3°F (6.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. You might also discover significant savings by opting for a longer stay. To find the ideal Vrbo property that fits your budget, use our handy filters to search by price, location, and type of vacation rental. Happy travels.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you create new travel plans, keep your existing arrangements on track, and manage your bookings with ease. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for your convenience. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Head to the historic city of San Gimignano

Come and experience San Gimignano and its history, museums and cathedral. This walkable city is known for its cafes, wineries and monuments. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around San Gimignano

Are you searching for things to do in the area? Venture out of your cozy vacation rental and experience everything that makes San Gimignano a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Sovestro in Poggio Winery (0.9 mi / 1.5 km)
  • Tenuta Torciano Winery (3.5 mi / 5.6 km)
  • Castello di Monsanto (7.5 mi / 12.1 km)
  • Castello della Paneretta (8 mi / 12.9 km)
  • Casa Sola - Chianti Winery (10 mi / 16.1 km)
  • Isole e Olena Winery (10 mi / 16.2 km)

Exploring the natural landscape of San Gimignano

Whether you're an active traveler or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in San Gimignano. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Sentierelsa Trail (5.3 mi / 8.6 km)
  • Alta Val d'Elsa River Park (7.1 mi / 11.4 km)
  • Chianti Sculpture Park (17.7 mi / 28.5 km)
  • Val di Merse (22.1 mi / 35.6 km)
  • Arno River (23.3 mi / 37.5 km)
  • Le Caldane Thermal Baths (7 mi / 11.3 km)

Traveling to and around San Gimignano

The nearest airport is in Florence Airport, Peretola (FLR), located 24.4 mi (39.3 km) from the city center.

Frequently asked questions

What is the best area to stay in San Gimignano when booking a vacation rental?
When considering a vacation rental in San Gimignano, the historic centre is the best area to stay. This UNESCO World Heritage Site is famed for its medieval towers and charming narrow streets, making it an enchanting backdrop for your Tuscan escape. In this area, you'll be close to top attractions such as the stunning Duomo di San Gimignano, known for its remarkable frescoes, and the iconic Piazza della Cisterna, where you can enjoy a gelato while soaking in the vibrant atmosphere.

Another excellent option is the surrounding countryside, which offers a more tranquil experience while still being just a short walk from the town centre. This area is great for those who appreciate scenic landscapes and vineyards, with ample opportunities for wine tasting and exploring the rolling hills of Tuscany. There are numerous properties available here, suiting various tastes, from rustic farmhouses to modern villas.
How much does it cost to rent a vacation home in San Gimignano?
Prices for vacation rentals in San Gimignano vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in San Gimignano to more spacious homes.
Are there any discounts for San Gimignano vacation house rentals?
You can find great discounts on house rentals in San Gimignano on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in San Gimignano?
In San Gimignano, apartments are the most popular type of vacation rental, with around 216 available throughout the historic town. These apartments are often situated within charming medieval buildings, providing a special environment that reflects the local culture. Most come equipped with fully furnished kitchens, comfortable living areas, and some even feature balconies with stunning views of the surrounding Tuscan countryside.
Are there any family house rentals in San Gimignano?
In San Gimignano, Tuscany, there are numerous family-friendly vacation rentals available, with around 205 options to choose from. This picturesque medieval town is not only renowned for its stunning towers and historic charm but also offers a variety of spacious homes superb for families. Many of these properties feature multiple bedrooms, expansive living areas, and fully equipped kitchens, making it easy to prepare meals together.

Visitors will appreciate amenities such as private gardens or terraces where children can play, as well as swimming pools for relaxing after a day of exploring. The town itself, with its cobbled streets and vibrant piazzas, is ideal for strolls, and nearby attractions include local vineyards and the beautiful Tuscan countryside, superb for family outings.
Can I rent a vacation home with a pool or hot tub in San Gimignano?
In San Gimignano, there are plenty of vacation homes available for rent that feature pools or hot tubs, with approximately 245 options to choose from. This picturesque town, renowned for its medieval architecture and stunning countryside views, offers a range of properties in various neighbourhoods, including the tranquil rural areas surrounding the town and its historic centre. Find your rental in San Gimignano with a pool or a hot tub.
Can I find long-stay vacation rentals in San Gimignano?
A long-stay vacation rental in San Gimignano is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in San Gimignano?
In San Gimignano, there are numerous pet-friendly house rentals available, offering a delightful blend of rustic charm and modern amenities. Many properties feature spacious gardens, private terraces, and stunning views of the surrounding Tuscan countryside, allowing pets to roam freely while owners enjoy the picturesque landscape. Inside, travellers can expect well-equipped kitchens, comfortable living areas, and often a touch of traditional Tuscan decor, creating a friendly setting for both pets and their owners.
Are there any remote work vacation rentals in San Gimignano?
In San Gimignano, Tuscany, there are numerous options for remote work vacation rentals, with around 309 available throughout the area. This picturesque medieval town, famous for its stunning towers and rich history, offers a variety of properties that cater to remote workers. Many rentals come equipped with dedicated workspaces, including desks and chairs, ensuring a comfortable environment for productivity. High-speed Wi-Fi is commonly provided, along with essential amenities such as safes for securing valuables and computer monitors for a more efficient workflow. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any San Gimignano vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in San Gimignano with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in San Gimignano?
In San Gimignano, popular rental amenities include essential features that enhance the comfort of guests. Most vacation rentals come equipped with kitchens, allowing travellers to prepare their own meals and enjoy the local produce. Many properties also offer complimentary Wi-Fi, ensuring guests can stay connected during their visit. Refrigerators are standard in the accommodations, making it easy to store snacks and drinks. Additionally, some rentals boast inviting pools, great for a refreshing dip on warm Tuscan days. Ovens are also commonly found in these properties, providing flexibility for cooking and baking.
When is the best time to visit San Gimignano for a vacation rental?
The best time to visit San Gimignano for a vacation rental is during November, when the charming medieval town is less crowded yet brimming with life. As the peak season runs from November to January, this month is particularly appealing for those seeking a blend of tranquillity and vibrant local culture.

During this time, the weather is mild, with average temperatures around 10 to 15 degrees Celsius, making it comfortable for outdoor activities and leisurely strolls through the cobblestone streets. Visitors can enjoy exploring the iconic towers and sampling the local cuisine at various trattorias without the hustle and bustle of larger crowds.

For those looking for a more budget-friendly option, October offers a beautiful opportunity to witness the grape harvest season in Tuscany. The landscape is adorned with stunning autumn colours, and the atmosphere is delightfully serene, superb for scenic drives through the picturesque countryside.
How early should I book a San Gimignano vacation rental?
Book your San Gimignano vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in San Gimignano?
In San Gimignano, visitors can take part in a variety of attractions that showcase the town's rich history and stunning architecture. The historic centre, a UNESCO World Heritage Site, is renowned for its medieval towers, particularly the iconic Torre Grossa, which offers panoramic views of the surrounding Tuscan countryside. Vacation rentals in the heart of the town provide easy access to charming piazzas, local shops, and authentic trattorias.

Art enthusiasts will appreciate the Collegiate Church of Santa Maria Assunta, home to magnificent frescoes by renowned artists such as Domenico Ghirlandaio. The Piazza della Cisterna, lined with restaurants and cafés, serves as a picturesque gathering spot and is great for enjoying gelato while soaking in the medieval atmosphere.
Can I change or cancel my San Gimignano home rental booking on Vrbo?
To find San Gimignano vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the San Gimignano vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Ideas