San Gimignano holiday lettings

We found 3,228 holiday rentals — enter your dates for availability

Select from 44 houses, 137 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:22 May - 29 May

Image gallery for Macinella Friendly and Artistic apartment "Sunflower 1"

Living area
9.2 out of 10, Wonderful, (24 reviews)
Wonderful
(24 reviews)

Macinella Friendly and Artistic apartment "Sunflower 1"

San Gimignano

9% off
Price is £1,260
for 7 nights, 1 villa
£180 per night
includes taxes & fees
Macinella Friendly and Artistic apartment "Sunflower 1"

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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:

  • 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)
  • Castelvecchio Natural Reserve (2.9 mi / 4.6 km)
  • Sentierelsa Trail (5.3 mi / 8.6 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?
When considering a holiday rental in San Gimignano, a charming medieval town in Tuscany, the historical centre is the best area to stay. This picturesque neighbourhood is renowned for its stunning towers and well-preserved architecture, offering visitors an authentic glimpse into the past. The area boasts a range of holiday properties, from quaint apartments to more luxurious options, allowing for a delightful stay amidst the town's captivating atmosphere.

While in the historical centre, you can easily explore top attractions such as the Collegiate Church of Santa Maria Assunta, which showcases incredible frescoes and a stunning interior, and the Piazza della Cisterna, a lovely square great for enjoying a gelato while soaking in the vibrant surroundings.
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.
Where are the best areas for renting a beach house in San Gimignano?
For renting a beach house near San Gimignano, it's important to note that the town itself is situated inland and is not directly on the coast. However, there are lovely areas along the Tuscan coastline that are within a reasonable drive, particularly towards the seaside towns of San Vincenzo and Castiglione della Pescaia.

In the San Vincenzo area, visitors can find beach houses that offer stunning views of the Tyrrhenian Sea, often featuring amenities such as private terraces, outdoor dining areas, and easy access to sandy beaches. Many properties in this region come equipped with modern kitchens, making it convenient for families or groups to prepare meals and enjoy al fresco dining while soaking in the coastal atmosphere.

If you venture further south to Castiglione della Pescaia, you'll discover charming villas and beachfront apartments that cater to holidaymakers. Here, amenities frequently include private pools, garden spaces, and proximity to local shops and restaurants, allowing for a comfortable and enjoyable stay. The beaches are typically well-maintained and ideal for sunbathing or enjoying water sports.

While San Gimignano itself is renowned for its medieval architecture and stunning hilltop views, the nearby coastal areas offer the great complement for travellers seeking both cultural experiences and beach relaxation.
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 approximately 756 available throughout the charming medieval town. These apartments typically offer amenities such as fully equipped kitchens, comfortable living areas, and often stunning views of the surrounding Tuscan countryside. Many are located near key attractions like the iconic towers, the Collegiata di Santa Maria Assunta, and local vineyards, making them ideal for exploring the rich history and culture of the area.

In addition to apartments, there are around 256 villas and 240 holiday houses, which cater to those seeking more space and privacy. These properties often feature multiple bedrooms, private gardens, and outdoor patios, allowing guests to enjoy the beautiful Tuscan weather. For a more rustic experience, there are also a small number of cottages and several campsites available, providing a range of options for different preferences and group sizes.
Are there any family house rentals in San Gimignano?
In San Gimignano, Tuscany, there is a wide selection of family-friendly holiday rentals, with around 171 available. This charming medieval town is renowned for its stunning towers and picturesque landscapes, making it a wonderful choice for families. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces for children to play and enjoy the Tuscan sun.

Visitors can find accommodations in various neighbourhoods, each offering unique access to local attractions. For instance, homes located near the historic centre allow easy exploration of the town's famous squares, like Piazza della Cisterna, as well as art galleries and delightful gelaterias. Additionally, properties situated on the outskirts often come with beautiful gardens and views of the rolling hills, providing a peaceful retreat after a day of sightseeing.

Family-oriented amenities such as Wi-Fi, air conditioning, and sometimes even swimming pools can be expected, ensuring a comfortable stay.
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 come equipped with pools or hot tubs, with around 204 options to choose from. This picturesque town in Tuscany is renowned for its medieval towers and beautiful landscapes, making it a delightful destination for travellers seeking relaxation and adventure.

You can find these properties scattered throughout the surrounding countryside and in the town itself, often featuring stunning views of the vineyards and rolling hills. Many rentals have private pools, outdoor terraces for al fresco dining, and hot tubs, providing a luxurious setting to unwind after exploring the area's rich history and cultural sites.

Expect amenities such as fully equipped kitchens, spacious living areas, and charming outdoor spaces, ideal for families or groups wanting to enjoy the tranquil Tuscan atmosphere. Additionally, the proximity to local wineries and traditional trattorias enhances the experience, allowing guests to indulge in the region's culinary delights. 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, with around 155 options to choose from. This enchanting medieval town in Tuscany offers a variety of holiday homes that cater to travellers with pets. Many of these rentals feature spacious gardens or outdoor terraces, providing ample space for pets to roam and play. Inside, guests can expect comfortable amenities such as well-equipped kitchens, Wi-Fi, and cosy living areas, superb for relaxing after a day of exploring the town's historic attractions.

The area is rich in cultural heritage, with the iconic towers of San Gimignano and charming cobblestone streets to wander through. Additionally, nearby parks and countryside trails offer excellent opportunities for walking and enjoying nature with pets. The surrounding Tuscan landscape, dotted with vineyards and olive groves, is ideal for leisurely strolls, making it a delightful destination for both pet owners and their furry companions.
Are there any remote work holiday rentals in San Gimignano?
In San Gimignano, Tuscany, there are numerous options for remote work holiday rentals, with around 1,060 properties available. This picturesque medieval town offers a unique blend of history and modern amenities, making it an excellent choice for those looking to work remotely. Many of the rentals come equipped with reliable Wi-Fi, ensuring a seamless connection for virtual meetings or work tasks.

Travellers can expect a variety of accommodations, from charming apartments in the town's historic centre to spacious villas set amidst the stunning Tuscan countryside. Common amenities often include comfortable workspaces, fully equipped kitchens for self-catering, and outdoor areas where one can relax after a day of work. The proximity to local attractions, such as the iconic towers and beautiful vineyards, adds to the appeal of working from this enchanting destination. 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, holiday rentals often feature a variety of popular amenities that enhance the guest experience. Most properties come equipped with a kitchen, allowing visitors to prepare their own meals and enjoy the local produce. Onsite parking is commonly available, making it convenient for those travelling by car. Many rentals also permit pets, accommodating furry companions during the stay. Additionally, you can expect amenities like coffee and tea makers for those essential morning brews, as well as provisions for service animals, ensuring a comfortable stay for all guests.
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 period marks the peak season, running from November to January, when the charming medieval town is adorned with festive decorations, and the atmosphere is filled with warmth and celebration.

With mild temperatures ranging from 5 to 15 degrees Celsius, November provides a comfortable climate for outdoor activities and sightseeing. You can explore the town's iconic towers and winding streets, and enjoy the stunning Tuscan countryside, all while indulging in local wine tastings and delicious cuisine.

If you're looking for a more budget-friendly option, consider visiting in October. This month is less crowded but still offers delightful experiences, such as the grape harvest festival, where you can immerse yourself in the local culture and enjoy the vibrant autumn colours.

Ultimately, your choice will depend on whether you prefer the bustling energy of the peak season in November or the quieter charm of October, where you can enjoy the beauty of San Gimignano at a more relaxed pace.
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 engage in a rich tapestry of history and culture. The town is famed for its medieval towers, with the Torre Grossa being the tallest and offering stunning views of the surrounding countryside. The historic centre, a UNESCO World Heritage Site, is filled with charming cobblestone streets and ancient buildings that showcase the town's architectural heritage.

The Piazza della Cisterna is a central gathering place, surrounded by delightful cafés and shops, making it a great spot to relax and enjoy local delicacies such as the renowned Vernaccia di San Gimignano wine. Nearby, the Collegiate Church of Santa Maria Assunta features impressive frescoes that captivate art enthusiasts.

For those interested in local history, the San Gimignano 1300 Museum provides a fascinating glimpse into the town's past through intricate models and exhibits.
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 cabin or a beach house, 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 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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