San Gimignano vacation rentals

We found 3,215 vacation rentals — enter your dates for availability

Select from 49 houses, 135 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.

Holiday rentals with weekly discounts - San Gimignano

Showing deals for:Aug 21 - Aug 28

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Find out more about San Gimignano

Why visit San Gimignano

  • Rich Cultural Heritage: Discover charming churches, fascinating museums, and historic castles that reflect San Gimignano's deep history.
  • Breathtaking Views: Enjoy stunning panoramas of the Tuscan countryside and picturesque town scenery.
  • Romantic Atmosphere: Experience the enchanting ambiance perfect for couples seeking a getaway.
  • Outdoor Activities: Explore the beautiful surroundings and indulge in outdoor adventures in the scenic Chianti region.
  • Unique Accommodations: Choose from charming apartments to luxurious villas for a memorable stay.

Popular types of accommodation in San Gimignano

Planning a getaway to San Gimignano? The next step is finding the perfect place to stay. From charming apartments to spacious houses and luxurious villas, there’s something for everyone. Imagine relaxing in a luxury villa rental with a private swimming pool, complete with fresh bed linens for your comfort. Explore the best vacation rental options that offer both tranquility and style for an unforgettable experience.

  • Apartments: The top choice for travelers in San Gimignano, offering convenient and comfortable living spaces for your stay.
  • Houses: A favored option for groups, providing a homey atmosphere and privacy for families and friends.
  • Villas: Luxurious accommodations that promise stunning views and spacious living for a memorable getaway.
  • Caravan Parks: A unique lodging option for outdoor enthusiasts, perfect for camping and mobile homes.
  • Cottages: Charming and cozy, these quaint retreats are ideal for a peaceful escape.**

Top attractions in San Gimignano

San Gimignano is perfect for those seeking a romantic, cultural, and outdoor vacation. Visitors can explore a variety of attractions, including charming churches, fascinating museums, and historic castles. This picturesque town offers a blend of rich cultural experiences and stunning city views, making it an ideal destination for travelers looking to immerse themselves in history and romance.

  • San Gimignano Communal Palace: A historic civic government building that embodies the rich culture of San Gimignano. Its impressive architecture and historical significance provide a glimpse into the town's past and the governance of medieval Tuscany.
  • Piazza Duomo: This vibrant square is the heart of San Gimignano, surrounded by stunning architecture and lively atmosphere. It's a perfect spot for people-watching, enjoying local cuisine, and soaking in the city's cultural essence.
  • Medieval Criminal and Torture Museum: A fascinating museum that delves into the darker aspects of medieval justice. Exhibits include historical artifacts and informative displays that illuminate the grim realities of crime and punishment in the past.

Things to do recommended for couples

For a romantic getaway in San Gimignano, savor exquisite wines at Tenuta Torciano Winery, indulge in a cozy dinner at Torre del Porcellino, and enjoy the outdoor charm at Tenuta Maiano. These experiences promise unforgettable moments for couples in the heart of Tuscany.

Things to do recommended for families

Your family will enjoy the excitement at Siena Stadium and Palasport Mens Sana, both 16 miles from San Gimignano, or catch a game at Stadio Artemio Franchi, located 17 miles away. These venues offer a vibrant sports atmosphere that's perfect for family fun.

Things to do recommended for groups

Explore the scenic Sentierelsa Trail, just a 5-mile hike from San Gimignano, or immerse in culture at Teatro del Silenzio, 15 miles away. For sports enthusiasts, the Castelfalfi Golf Course, located 11 miles from town, offers a perfect outdoor retreat for your group.

*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

If you're traveling with a group, your family, bringing along pets, or planning an extended stay, be sure to set your filters according to your top priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to San Gimignano with a group: Think about how many bedrooms you’ll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to San Gimignano with young kids: Traveling with young kids can be quite a task. 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 is a smart move.
  • Taking your pets with you to San Gimignano: For many, a family vacation wouldn't be the same without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting San Gimignano: If you’re in search of vacation rentals offering discounts for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search for the best options.

Where to stay in San Gimignano

San Gimignano offers a captivating blend of culture, romance, and outdoor adventures in the heart of Tuscany. Visitors can explore the idyllic setting of this historic city, complete with stunning views and charming Tuscan villas. The nearby Chianti region invites travelers to experience the friendly atmosphere and luxury of this beautiful part of Italy, making it the perfect getaway for those seeking relaxation and unique experiences.

  • San Gimignano City Centre: The heart of San Gimignano, the City Centre is a captivating blend of history and culture. This neighborhood is renowned for its striking medieval towers and well-preserved architecture, making it a UNESCO World Heritage Site. Visitors can enjoy outdoor activities, family-friendly attractions, and cultural experiences. Popular venues include charming theaters and relaxing spas. Local landmarks such as historic sites and vibrant tourist precincts invite exploration, offering a unique glimpse into the town's storied past.
  • Castel San Gimignano: Nestled in the hills, Castel San Gimignano is a picturesque village exuding romance and charm. This quaint area offers a serene atmosphere, perfect for leisurely walks and tours of its scenic surroundings. Travelers can immerse themselves in the culture while exploring historic civic buildings and the central piazza. The village is also known for its delightful entertainment options, making it a great destination for couples seeking a memorable experience amidst Tuscany's stunning landscapes.
  • Ulignano: Ulignano is a charming village that offers a romantic and outdoor experience for visitors. Surrounded by lush countryside, this village is perfect for those seeking relaxation and rejuvenation. Enjoy body treatments at local spas or indulge in outdoor activities that showcase the beautiful Tuscan landscape. Nearby attractions include historic homes and quaint piazzas where you can soak in the local ambiance. Ulignano is a hidden gem that invites exploration and offers a peaceful retreat from the bustling tourist spots.

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

Are you planning to save on your upcoming travel adventure? Consider being flexible with your travel dates, as this can lead to better pricing options. Additionally, booking a longer stay can result in substantial savings. To discover a Vrbo property that suits your budget, feel free to utilize our filters to narrow down your search by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo's Trip Board feature offers you a convenient way to plan your trips. You can easily create new travel itineraries, pick up right where you left off, or manage and organize your travel plans. All the properties you've saved or booked before are now accessible under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

San Gimignano: the perfect Tuscan town

If there was a model Tuscan town, the one you see on the front cover of guidebooks, it would be San Gimignano. The town, along with its pretty skyline of 13th-century towers, is perched on top of a Tuscan hill surrounded by the old city walls and sweeping cypress trees. When you come to stay in a San Gimignano vacation rental, you'll quickly realize why it was designated a UNESCO World Heritage Site. You'll feel like you've stepped back in time when you wander along the narrow streets, which open onto a sunny piazza flanked by gorgeous Medieval buildings.

San Gimignano is bursting with cultural attractions

When you pop out of your San Gimignano vacation rental, you'll find a town which is easily explored by foot and, though small, it's bursting at the seams with things to see. You could start your day with a cappuccino and pastry in the sunny piazza, before discovering the ancient artwork inside the Palazzo Comunale. Afterwards, you'll be puffed out when you climb the Torre Grossa, but the views from the top are worth the effort. In the afternoon, grab yourself that obligatory, and delicious, Italian gelato and then dive into the rather grizzly but fascinating Medieval Torture Museum.

The rolling hills of San Gimignano await

Italy has always been about good food, good wine and good company, and Tuscany is no exception. Staying in a San Gimignano vacation rental puts you in the heart of these rolling hills. Whether you go by car or by bicycle, it's unthinkable not to drop into one of the Chianti wineries, to sample some of the country's finest reds. To learn the art of Tuscan cuisine, you should consider taking the family to one of the many cooking classes on offer, where you can learn about Italian produce and try your hand at cooking fresh pasta dishes.

Spring and fall are San Gimignano's sweet spot

While the summer months see the most glorious weather, with little rain and endlessly bright skies, it also attracts the biggest crowds, who book up the San Gimignano vacation rentals. If you don't mind a slightly cooler temperature, arguably better if you plan to hike or bike, try to nab a rental between April and May or September and October, when the summer crowds are back at home and the town feels decidedly more quiet and local. For rock-bottom prices, you could visit in winter, when you'll likely be the only foreigner in town but expect cold and rainy weather.

San Gimignano lies close to nature

While you're staying in a San Gimignano vacation rental, it would be a shame to miss the 700-hectre Castelvecchio, a forest-covered nature reserve just a short drive away. This wild land holds your best chances of spotting wildlife in Tuscany. If you take a hike through the park, you'll likely encounter several critters including deer, red foxes and the occasional wild boar which rustles around on the forest floor, not to mention the scampering hares and porcupines. If you look up to the treetops and towards the marshes, there's more to see, including tawny owls, pheasants and beautiful herons.

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, Tuscany, Italy when booking a vacation rental?
When considering a stay in San Gimignano, Tuscany, one of the best areas to book a vacation rental is within the historic center. This charming area is characterized by its medieval architecture and stunning towers, offering an immersive experience in the town's rich history. You'll have easy access to top attractions such as the beautiful Piazza della Cisterna, where you can enjoy local gelato and savor the atmosphere, as well as the Collegiate Church of San Gimignano, renowned for its stunning frescoes.

Another appealing option is to explore the surrounding countryside. This area offers a peaceful retreat with breathtaking views of the rolling hills and vineyards typical of Tuscany. Staying here allows you to relax away from the hustle and bustle while still being just a short drive or bike ride from the town's main attractions.

Both areas provide a variety of properties, ranging from quaint apartments to cozy villas, ensuring there's something to suit every preference and budget.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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 common vacation rental option, with about 189 available throughout the picturesque town. These apartments are often situated in charming, historic buildings and typically feature amenities such as fully equipped kitchens, cozy living areas, and sometimes balconies that offer stunning views of the surrounding Tuscan countryside. The town's rich history, with attractions like the famous towers and the Piazza della Cisterna, is easily accessible from these accommodations.

Additionally, there are around 64 villas and 60 vacation houses available for those seeking more space and privacy. These properties often include multiple bedrooms, private gardens, and outdoor dining areas, making them ideal for families or groups looking to enjoy a relaxing retreat in the heart of Tuscany.
Are there any family house rentals in San Gimignano?
In San Gimignano, Tuscany, there are numerous family-friendly vacation rentals available, with around 171 options throughout the area. This picturesque town, known for its medieval towers and stunning landscapes, offers a variety of homes superb for families. Many properties come equipped with spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play or families can enjoy al fresco dining while taking in the beautiful surroundings.

Visitors will find that these rentals often feature amenities such as Wi-Fi, swimming pools, and serene gardens, enhancing the comfort of their stay. The historical charm of San Gimignano is complemented by nearby attractions, including local vineyards and the famous San Gimignano 1300 Museum, which showcases the town's rich history. See all family-friendly rentals in San Gimignano.
Can I rent a vacation home with a pool or hot tub in San Gimignano?
In San Gimignano, Tuscany, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 204 options to choose from. This picturesque medieval town offers a stunning backdrop of rolling hills and vineyards, making it an ideal destination for travelers seeking relaxation and a taste of local culture. Many of the properties come equipped with private swimming pools, hot tubs, outdoor dining areas, and well-appointed kitchens, superb for enjoying the beautiful Tuscan weather and preparing meals with local ingredients.

Travelers can expect to find amenities like air conditioning, Wi-Fi, and spacious gardens, providing ample space for families or groups to unwind.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in San Gimignano?
In San Gimignano, travelers will find a wealth of pet-friendly house rentals, with around 155 options available. Many of these charming properties are located in the picturesque Tuscan countryside, offering stunning views of the rolling hills and vineyards that characterize the region. Guests can expect amenities such as outdoor terraces, spacious gardens, and fully equipped kitchens, making them ideal for families or groups traveling with pets.

The area is known for its historical significance and beautiful architecture, including the iconic medieval towers of San Gimignano, which create a unique backdrop for visitors. Additionally, nearby attractions like the scenic paths of the Chianti region provide fantastic opportunities for walks with pets, allowing travelers to explore the stunning landscapes at their leisure.
Are there any remote work vacation rentals in San Gimignano?
In San Gimignano, there is a robust selection of remote work vacation rentals, with around 265 options available. This picturesque town in Tuscany is renowned for its medieval towers and stunning landscapes, making it an ideal backdrop for remote work. Many of the properties come equipped with essential amenities such as high-speed Wi-Fi, allowing guests to stay connected while enjoying the serene environment.

Accommodations typically include cozy apartments and charming villas that offer comfortable workspaces, often with beautiful views of the surrounding vineyards and hills. Some rentals may also feature outdoor areas where one can work while soaking in the Tuscan sun or enjoying the scenic beauty.

Additionally, San Gimignano is rich in culture, with local markets, historical sites, and excellent dining options nearby, providing a great balance of productivity and leisure during your stay. 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 travelers 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 vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with local ingredients. Many rentals also offer onsite parking, which is particularly convenient for travelers exploring the picturesque Tuscan countryside. Additionally, some properties are pet-friendly, accommodating those who wish to bring their furry companions along. Travelers can expect amenities like coffee and tea makers for a cozy start to their mornings, and many rentals allow service animals, ensuring that all guests feel welcome.
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 the enchanting month of November. This marks the beginning of the peak season, which runs from November through January, drawing travelers eager to experience the charm of Tuscany. As the crowds thin out from the summer months, November offers a more relaxed atmosphere, allowing for intimate exploration of this historic hilltop town.

During this month, temperatures in San Gimignano typically hover in the mid-40s to low 60s Fahrenheit, creating a comfortable climate for outdoor activities and sightseeing. Visitors can stroll through the cobblestone streets, admire the iconic medieval towers, and savor the rich flavors of local cuisine without the bustling crowds that characterize the peak summer season. Additionally, the fall harvest season provides an excellent opportunity to indulge in wine tastings and local gastronomic delights.

For those seeking a more budget-friendly option, consider visiting in October, just before the peak season. This month also offers stunning autumn foliage and fewer tourists, making it a great time to enjoy the picturesque landscapes and explore nearby vineyards.
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, Tuscany, Italy?
In San Gimignano, visitors can engage in a rich tapestry of history and culture. The town is famously known for its medieval towers, with the iconic Torre Grossa offering breathtaking views of the surrounding Tuscan countryside. Just a short walk away, the Piazza della Cisterna serves as a central hub, surrounded by charming shops and eateries that highlight local cuisine.

The Collegiate Church of Santa Maria Assunta, located in the heart of San Gimignano, features stunning frescoes and is a must-visit for art lovers. Nearby, the Museo Civico showcases the town's artistic heritage and historical artifacts. For those interested in local wine, the area surrounding San Gimignano is renowned for its Vernaccia di San Gimignano, and many vineyards offer tastings and tours.

Exploring the quaint cobblestone streets, visitors can also discover artisan workshops and small galleries, further enriching their experience in this picturesque town.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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