San Gimignano holiday lettings

We found 3,564 holiday rentals — enter your dates for availability

Select from 64 houses, 259 apartments and other holiday rentals to find the perfect place for your stay in San Gimignano. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - San Gimignano

Showing deals for:17 Oct - 24 Oct
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Why visit San Gimignano

  • Cultural Heritage: Discover captivating churches and fascinating museums that showcase the rich history of San Gimignano.
  • Stunning Scenery: Revel in the breathtaking Tuscan landscape, perfect for outdoor enthusiasts and nature lovers.
  • Charming Villages: Explore nearby Chianti villages, offering a relaxed and welcoming atmosphere.
  • Romantic Ambiance: Enjoy the enchanting, romantic vibe perfect for couples seeking a getaway.
  • Delightful Accommodations: Choose from a variety of charming apartments and luxurious villas for a comfortable stay.

Popular types of accommodation in San Gimignano

Vrbo offers a delightful selection of vacation rentals in San Gimignano, perfect for every type of traveller. Whether you’re looking for charming apartments, spacious private homes, or luxurious villas, we have the ideal accommodation to suit your needs. Discover the beauty of Italy while enjoying the comfort of a villa rental or a lovely house rental. Whatever your preference, your perfect holiday retreat awaits!

  • Apartments: The top choice for visitors to San Gimignano, offering a convenient and comfortable base to explore the area.
  • Houses: A popular option for families and groups, providing a home-like atmosphere with added privacy.
  • Villas: Ideal for those seeking luxury, these spacious properties often come with stunning views and gardens.
  • Caravan Parks: A unique way to experience the countryside, perfect for those who enjoy outdoor living.
  • Cottages: Charming and quaint, these cozy retreats evoke a sense of rustic charm in the heart of Tuscany.**

Top attractions in San Gimignano

San Gimignano is an enchanting destination perfect for cultural, romantic, and outdoor getaways. Visitors can explore captivating churches, fascinating museums, and majestic castles, offering a rich blend of culture and city life. For those keen on sightseeing in Italy, this charming town provides a wealth of attractions that cater to diverse interests, ensuring a memorable experience for every traveller.

  • San Gimignano Communal Palace: This historic Civic Government Building is a testament to the town's rich history, offering a glimpse into its medieval past and showcasing local culture through its impressive architecture and art.
  • Piazza della Cisterna: A charming square at the heart of San Gimignano, Piazza della Cisterna is surrounded by beautiful towers and lively cafés, making it an ideal spot to soak up the vibrant city atmosphere and culture.
  • Medieval Criminal and Torture Museum: Dive into the darker side of history at this intriguing museum, which displays medieval instruments of punishment and explores the criminal justice system of the time, providing a unique cultural perspective.

Things to do recommended for couples

For a romantic getaway in San Gimignano, indulge in wine tasting at Tenuta Torciano Winery and savour delightful meals at Torre del Porcellino, just a short drive away. Don't forget to visit Tenuta Maiano for an enchanting outdoor experience amidst the vineyards.

Things to do recommended for families

Your family will love visiting the Chianti Observatory, just 6.8km from San Gimignano, where you can explore the wonders of the universe. For sports enthusiasts, Siena Stadium and Stadio Artemio Franchi, both within 16 and 10.6km respectively, offer thrilling sporting events for an exciting day out.

Things to do recommended for groups

Embark on the scenic Sentierelsa Trail for a memorable hike, enjoy a captivating performance at Teatro del Silenzio, or challenge yourselves at the Castelfalfi Golf Course. These activities promise adventure, culture, and fun for your group in beautiful San Gimignano.

Booking with Vrbo is simple

Planning to save on your upcoming holiday? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Where to stay in San Gimignano

San Gimignano, a gem in Tuscany, offers a delightful blend of history and romance, making it perfect for a culture-themed getaway. Explore charming Chianti villages nearby, where the atmosphere is relaxed and welcoming. Families will find idyllic settings for memorable moments, while outdoor enthusiasts can revel in the stunning Tuscan landscape. With its friendly locals and rich heritage, San Gimignano promises an enchanting experience that captures the essence of Italian beauty.

  • San Gimignano City Centre: The heart of San Gimignano, the City Centre is a UNESCO World Heritage site renowned for its medieval architecture and towers. Surrounded by stunning Tuscan countryside, this area offers a rich cultural experience with its historic sites, charming piazzas, and vibrant outdoor spaces. Visitors can indulge in local cuisine at family-run trattorias, explore boutique shops, or unwind at a spa. Key attractions include the Collegiate Church of Santa Maria Assunta and the Museum of San Gimignano, making it an ideal spot for those seeking culture and relaxation.
  • Castel San Gimignano: This picturesque village, perched on a hilltop, is an enchanting destination for couples and culture enthusiasts. Known for its romantic ambiance, Castel San Gimignano offers a blend of historical charm and entertainment. Stroll through its quaint streets, visit the local history museum, and enjoy guided tours that reveal the village's rich past. The village’s piazza is a perfect spot for a leisurely coffee while taking in the stunning surroundings. Don't miss the impressive historic civic government building, which adds to the village's allure.
  • Pancole: Nestled in the tranquil countryside, Pancole is a delightful village that invites outdoor enthusiasts and history buffs alike. With its scenic landscapes, it provides a perfect backdrop for romantic walks and cultural exploration. Visitors can admire the stunning architecture of the historic palace and church, as well as the charming civic government building. Pancole is an excellent base for hiking trails that lead through the breathtaking Tuscan hills, providing an immersive experience in nature and local heritage.

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 SunnyAverageAverage
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 HighSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnyAverageAverage

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

When planning your trip, whether you're travelling with a group, as a family, bringing along your pets, or seeking extended stays, it's essential to filter your options according to what matters most to you. Here are some helpful booking tips for using Vrbo.

  • Traveling to San Gimignano with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all these preferences, and much more, on Vrbo.
  • Traveling to San Gimignano with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to San Gimignano: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting San Gimignano: If you're in search of holiday rentals that offer discounts for stays of a month or more, you've come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for planning your travels, allowing you to create new trips, resume your previous arrangements, or review and organise your itinerary. You’ll find your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the historical 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 accommodation options with space to entertain friends and family, HomeAway 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 attractions to see during your stay? Venture out of your holiday home and experience everything that makes San Gimignano a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 outdoor enthusiast or just want to spend some time taking in the scenery, San Gimignano is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Arno River (23.3 mi / 37.5 km)
  • Le Caldane Thermal Baths (7 mi / 11.3 km)
  • Val di Merse (22.1 mi / 35.6 km)

Travelling to and around San Gimignano

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

Frequently asked questions

What is the best area to stay in San Gimignano when booking a holiday rental?
Pancole is one of the more popular areas to book a Vrbo holiday home in San Gimignano. Have a look at our collection of comfortable properties and then get ready to experience this destination like a local.
What is the most popular type of holiday rental accommodation in San Gimignano?
The most desirable types of holiday rentals in San Gimignano are apartments. Want something different? Vrbo has a variety of options to match our guests' diverse needs, so you'll see holiday homes in all shapes and sizes. The perfect fit is ready and waiting for you --- find yours today.
How much does it cost to rent a holiday rental in San Gimignano?
Different factors affect how much you'll pay for a holiday rental in San Gimignano, including the length of stay, season and type of property. But, all of our holiday homes have one thing in common --- amazing value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in San Gimignano?
The average price for a holiday home near the beach in San Gimignano depends on when you're travelling and the size and type of property you're looking for. You can quickly and easily find prices on Vrbo by entering your preferred travel dates and destination. Then use the filters to select the number of bedrooms and amenities that you require, like WiFi, a pool and air conditioning.
Are there pet-friendly holiday rentals in San Gimignano?
Pack a suitcase and a bone for the pooch in your life because San Gimignano has 144 holiday homes that throw open their doors to pets. Let your four-legged buddy join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in San Gimignano?
Mark the "pool" box in our filter tool and you can choose from 78 houses with private pools in San Gimignano on Vrbo. Gentle soak, ball games or noodle joust? Free time is up to you when your holiday property has its own pool.
What are popular rental amenities in San Gimignano?
When it comes to rental amenities that guests search for in San Gimignano, a firepit, mountain views and a chef are the most popular. With Vrbo holiday rentals, you'll have options to suit your taste and style, whether you're travelling with your partner, your friends or even pets.
Are there large group holiday rentals in San Gimignano?
San Gimignano has 14 holiday homes that can fit 10 or more guests. These stays come with the space you need to enjoy good times with family and friends.
Are there holiday rentals in San Gimignano that welcome kids?
San Gimignano has 142 family-friendly holiday rentals to pick from. And finding a stay that welcomes kids is a cinch with Vrbo's "Properties good for families" filter. In addition to having the whole place to yourselves, you can also look forward to perks and conveniences such as dining rooms, full kitchens and private pools.
What are the top attractions for families in San Gimignano?
There are tons of wonderful things to do and see with the family in San Gimignano, such as:

  • Castle of Oliveto
  • Podestas Palace
  • The Rock of Staggia

Are there one-bedroom holiday rentals in San Gimignano?
There are 55 one-bedroom properties in San Gimignano to pick from. A one-bedroom holiday rental is an excellent choice if it's just two of you or if you're travelling alone. Throw in more space, privacy and convenience compared to a standard hotel, and you've got the makings of an unforgettable getaway.
Can I find two-bedroom holiday rentals in San Gimignano?
Take off with your besties and experience complete comfort and privacy in one of the 41 two-bedroom holiday homes San Gimignano has to offer.
Are there holiday rentals with WiFi in San Gimignano?
San Gimignano has 72 holiday rentals with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to updating your social media, these Vrbo homes make it a cinch to go online.
How can I find holiday rentals with air conditioning in San Gimignano?
Pick your travel dates and then use our filters to locate holiday rentals with air conditioning in San Gimignano on Vrbo. With 83 air-conditioned properties available, you can enjoy a cool and comfortable break.
How old do you have to be to rent a holiday rental in San Gimignano?
The minimum age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so look at the rules of your preferred San Gimignano holiday home before booking your stay.
How long can I rent a holiday rental in San Gimignano for?
The amount of time you can book a San Gimignano holiday rental for varies depending on the property. Simply tap in your dates of travel to browse options that offer long-term stays. They feature all the things you need to make your extended break more comfortable such as kitchens and laundries. Some holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.