San Gimignano holiday lettings

We found 3,358 holiday rentals — enter your dates for availability

Select from 65 houses, 255 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:6 Feb - 13 Feb

Image gallery for Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Private pool
9.6 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

San Casciano in Val di Pesa, Tuscany

18% off
Price is £3,620
for 7 nights, 1 villa
£517 per night
includes taxes & fees
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

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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.

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.

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

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.

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)
  • 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)

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?
When planning a holiday in San Gimignano, one of the best areas to consider for a rental is the historic centre. This charming area is renowned for its medieval towers, and staying here allows you to immerse yourself in the town's rich history and vibrant atmosphere. You'll be just a short stroll away from iconic attractions such as the Collegiata di Santa Maria Assunta, famous for its stunning frescoes, and the Palazzo del Popolo, where you can enjoy magnificent views from the Torre Grossa.

Another lovely option is the surrounding countryside, which offers a peaceful retreat while still being within walking distance of the town. This area boasts numerous properties, often with stunning views of the rolling hills and vineyards typical of Tuscany. Staying here gives you the chance to experience the beautiful landscapes and perhaps visit local wineries, enhancing your holiday with authentic Tuscan flavours.
How much does it cost to rent a holiday home in San Gimignano?
Prices for holiday 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 holiday 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 holiday rental accomodation in San Gimignano?
In San Gimignano, apartments are the most popular type of holiday rental, with about 216 available throughout the charming medieval town. Many of these apartments are situated in the historic centre, providing easy access to landmarks such as the Torre Grossa and the Piazza della Cisterna. Most rooms 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 is a wealth of family-friendly holiday rentals available, with around 205 properties to choose from. This charming medieval town, known for its iconic towers and stunning countryside views, offers a variety of homes that cater to families. Many of these rentals boast spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play or families can gather for al fresco dining.

Visitors will find that some properties include amenities such as private pools, gardens, and even game rooms, ensuring entertainment for all ages. The picturesque landscape surrounding San Gimignano is superb for outdoor activities, with nearby hiking trails and vineyards to explore. Additionally, the town itself is rich in history, featuring local shops and eateries where families can sample traditional Tuscan cuisine.
Can I rent a holiday home with a pool or hot tub in San Gimignano?
In San Gimignano, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 245 options to choose from. This picturesque Tuscan town, famous for its medieval towers and stunning landscapes, offers a variety of properties located in the surrounding countryside and within the town itself. Find your rental in San Gimignano with a pool or a hot tub.
Can I find long-stay holiday rentals in San Gimignano?
A long-stay holiday 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 of these properties feature spacious gardens, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets. The picturesque town is known for its medieval towers and scenic landscapes, providing a superb backdrop for a relaxing holiday.
Are there any remote work holiday rentals in San Gimignano?
In San Gimignano, Tuscany, there are numerous remote work holiday rentals available, with around 309 options to choose from. This enchanting medieval town, famous for its stunning towers and rich history, provides an ideal backdrop for those looking to blend work and leisure. Many of the properties come equipped with essential amenities for remote work, including Wi-Fi, dedicated workspaces with desks and chairs, and even computer monitors in some cases. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any San Gimignano holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
The best time to visit San Gimignano for a holiday rental is during the enchanting month of November. This time of year marks the beginning of the peak season, which runs from November to January, drawing in travellers keen to experience the charm of this medieval town set against the stunning Tuscan landscape.

November offers a pleasant climate, with temperatures typically ranging from 10 to 15 degrees Celsius, making it an ideal time for leisurely strolls through the cobbled streets and exploring the iconic towers that define the skyline. With fewer crowds compared to the summer months, visitors can fully appreciate the rich history and culture of San Gimignano. Picture yourself sipping a glass of local Vernaccia wine at a quaint café, soaking in the picturesque views without the hustle and bustle of peak tourist season.

For those looking for a more budget-friendly option, October provides a wonderful alternative. With slightly cooler temperatures and the added bonus of the grape harvest season, this month allows you to enjoy the vibrant autumn colours while still experiencing the beauty of Tuscany without the high season prices.
How early should I book a San Gimignano holiday rental?
Book your San Gimignano holiday 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 holiday 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 immerse themselves in medieval history and stunning architecture. The town is renowned for its well-preserved towers, with the Torre Grossa being the tallest and offering panoramic views of the surrounding countryside. Holiday rentals in the historic centre allow easy access to the beautiful Piazza della Cisterna, where one can enjoy local gelato and the vibrant atmosphere.

The Collegiate Church of Santa Maria Assunta, with its remarkable frescoes, is another must-see, along with the nearby Palazzo del Popolo, which houses the town's museum. For those interested in the local wine scene, many properties in the area are conveniently located near vineyards that produce the famous Vernaccia di San Gimignano.
Can I change or cancel my San Gimignano home rental booking on Vrbo?
To find San Gimignano holiday 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 holiday 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.

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