Castel San Gimignano holiday rentals

We found 1,183 holiday rentals — enter your dates for availability
Discover a selection of 5 apartments and other holiday rentals in Castel San Gimignano that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Head to the cosy city of Castel San Gimignano

Enjoy the wineries and other features of Castel San Gimignano. This city is welcoming and walkable, recognised for its cheese shops, coffee shops and local tours. 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.

Sightseeing in and around Castel San Gimignano

Do you want to discover attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Castel San Gimignano a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sovestro in Poggio Winery (4.3 mi / 6.9 km)
  • Tenuta Torciano Winery (7.9 mi / 12.7 km)
  • Castello di Monsanto (10.5 mi / 16.9 km)
  • Castello della Paneretta (11.1 mi / 17.8 km)
  • Castelfalfi Golf Course (12.5 mi / 20.2 km)
  • Isole e Olena Winery (13 mi / 20.9 km)

Exploring the natural features in Castel San Gimignano

Whether you're an adventurous traveller or just want to appreciate the scenery, Castel San Gimignano is a great place to spend some time outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Alta Val d'Elsa River Park (5.8 mi / 9.3 km)
  • Val di Merse (18.8 mi / 30.3 km)
  • Sentierelsa Trail (5.7 mi / 9.2 km)
  • Le Caldane Thermal Baths (5.8 mi / 9.4 km)
  • Castelvecchio Natural Reserve (3.6 mi / 5.8 km)
  • The SottoVico Garden (8.4 mi / 13.5 km)

How to get to and around Castel San Gimignano

Fly into Peretola Airport (FLR), the closest airport, located 29 mi (46.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Castel San Gimignano when booking a holiday rental?
When considering a holiday rental in Castel San Gimignano, the historic centre is the best area to stay. This charming neighbourhood is renowned for its medieval architecture, including the iconic towers that define the skyline. Staying here allows you to immerse yourself in the rich history and culture of the region, with easy access to attractions such as the stunning Collegiate Church of Santa Maria Assunta and the fascinating Museo della Tortura, which provides insight into the darker aspects of medieval life.Another appealing area is the surrounding countryside, where you can find a variety of properties set amidst the picturesque Tuscan landscape. This option offers a tranquil retreat with opportunities for outdoor activities, such as hiking and wine tasting at local vineyards. The number of properties available in these areas varies, providing a range of choices from charming apartments to luxurious villas.
When is the best time to visit Castel San Gimignano for a holiday rental?
The best time to visit Castel San Gimignano for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant period sees the Tuscan sun shining brightly, offering warm temperatures ranging from 25 to 35 degrees Celsius, superb for exploring the stunning medieval architecture and picturesque landscapes.During these summer months, the charming streets of Castel San Gimignano come alive with visitors eager to enjoy local wine, delicious cuisine, and the rich culture that the region has to offer. You can take leisurely walks through the historic centre, visit local vineyards, and savour the flavours of Tuscany while soaking in the breathtaking views.If you're looking for a more tranquil experience at a better value, consider visiting in November. While the weather is cooler, typically around 10 to 15 degrees Celsius, this off-peak month allows you to appreciate the region's beauty without the crowds. You can enjoy the peaceful atmosphere, picturesque autumn colours, and even partake in the olive oil harvest, providing a unique insight into local traditions.
What are the top attractions in Castel San Gimignano?
In Castel San Gimignano, visitors can immerse themselves in the rich history and stunning architecture of this charming medieval town. The iconic towers of San Gimignano, a UNESCO World Heritage site, dominate the skyline and can be explored through winding streets lined with quaint shops and local eateries. The Collegiate Church of Santa Maria Assunta, adorned with beautiful frescoes, is a must-visit for art enthusiasts.For those interested in local culture, the town hosts the Vernaccia di San Gimignano wine festival, celebrating its famous white wine. The nearby San Gimignano 1300 museum provides a fascinating glimpse into the town's history through detailed dioramas. Additionally, the surrounding countryside offers picturesque landscapes, superb for leisurely walks or bike rides, with vineyards and olive groves creating a quintessential Tuscan atmosphere.
Are all fees included in the Castel San Gimignano holiday homes prices shown on Stayz?
Stayz 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.
Are there any Castel San Gimignano holiday homes with parking?
Stayz offers a wide selection of holiday homes in Castel 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 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.
Are there any discounts for Castel San Gimignano holiday homes?
You can find great discounts on holiday homes in Castel San Gimignano on Stayz, 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.
Can I change or cancel my Castel San Gimignano holiday home booking on Stayz?
To find Castel San Gimignano holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Castel San Gimignano?
A long-stay holiday home in Castel 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Castel San Gimignano holiday home?
Book your Castel San Gimignano holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Castel San Gimignano?
Prices for holiday homes in Castel San Gimignano vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Castel San Gimignano to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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