San Gimignano vacation rentals

We found 3,467 vacation rentals — enter your dates for availability

Select from 59 houses, 252 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.
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Find out more about San Gimignano

Find out more about San Gimignano

Why visit San Gimignano

  1. Rich cultural heritage: Explore stunning churches, museums, and historic castles that showcase San Gimignano's fascinating history.
  2. Scenic views: Enjoy breathtaking panoramas of the Chianti Hills and tranquil meadows, perfect for outdoor relaxation.
  3. Charming ambiance: Stroll through the picturesque streets and soak in the town's romantic atmosphere.
  4. Diverse accommodations: Choose from cozy apartments, private homes, and luxurious villas catering to various preferences.
  5. Friendly local community: Experience the warm hospitality and welcoming vibe of the San Gimignano locals.

Popular types of accommodation in San Gimignano

Planning a getaway to San Gimignano? You're in for a treat! Discover a range of vacation rentals, including charming apartments, houses, and luxurious villas. Whether you're looking for cozy apartment rentals or spacious villas in San Gimignano, we have options that cater to every traveler's needs. Enjoy your stay with the confidence of transparent information and great savings!

  • Apartments: A top choice for travellers, these self-contained spaces offer convenience and comfort for individuals or groups.
  • Houses: Ideal for families or friends, these homes provide a homey atmosphere and ample space for relaxation.
  • Villas: Known for their luxury and stunning views, villas are perfect for those seeking an upscale experience.
  • Caravan Parks: A delightful option for adventurers, offering a chance to connect with nature while enjoying communal facilities.
  • Cottages: Quaint and charming, cottages provide a cozy retreat for a peaceful getaway.**

Top attractions in San Gimignano

San Gimignano offers a delightful blend of culture, romance, and outdoor experiences, making it an ideal destination for Canadian tourists. Visitors can explore stunning churches, fascinating museums, and historic castles, all of which showcase the town's rich heritage. Whether you seek a romantic getaway or a cultural adventure, San Gimignano has a variety of attractions to cater to every traveler's interests, ensuring a memorable vacation in the heart of Tuscany.

  1. San Gimignano Communal Palace: This historic Civic Government Building showcases the rich cultural heritage of San Gimignano, featuring stunning architecture and art that reflect the town's medieval past.
  2. Piazza della Cisterna: A charming square surrounded by medieval buildings, this vibrant piazza is the perfect place to experience local culture, enjoy a gelato, and soak in the lively atmosphere.
  3. Medieval Criminal and Torture Museum: Dive into the darker side of history at this intriguing museum, where exhibits on medieval justice and punishment provide a unique and thought-provoking experience.

Things to do recommended for couples

For a romantic getaway in San Gimignano, visit Tenuta Torciano Winery for a delightful wine tasting experience. Enjoy a meal at Torre del Porcellino, just 16.1km away, and unwind at Tenuta Maiano, where outdoor charm awaits. Create unforgettable memories in the heart of Tuscany!

Things to do recommended for families

Discover the wonders of the Chianti Observatory, only 17.7km from San Gimignano, perfect for curious minds. Enjoy a thrilling day at nearby sports facilities like Stadio Carlo Castellani and Siena Stadium, both offering exciting sporting events for the whole family to enjoy.

Things to do recommended for groups

Your group vacation in San Gimignano will be unforgettable! Hike the scenic Sentierelsa Trail, enjoy the cultural experience at Teatro del Silenzio, and tee off at Castelfalfi Golf Course for some outdoor fun. Each activity promises adventure, entertainment, and beautiful Tuscan landscapes.

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

If you're planning a trip with a group, family, bringing along your pets, or seeking extended stays, it's important to prioritize your search effectively. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to San Gimignano with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options, and more, on Vrbo.
  • Traveling to San Gimignano with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, as well as look for suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your overall experience.
  • Taking your pets with you to San Gimignano: For many families, a getaway isn't truly fulfilled without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your 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 stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in San Gimignano

San Gimignano offers a charming blend of history and romance, making it an ideal destination for culture lovers. Explore the lovely town’s outdoor seating areas while soaking in the breathtaking views of the Chianti Hills. The nearby meadows provide a tranquil escape, showcasing the serene Tuscan countryside. Whether you’re wandering through historical streets or enjoying the friendly atmosphere, your experience in and around San Gimignano promises to be unforgettable.

  • San Gimignano City Centre: The heart of San Gimignano, this vibrant city centre is renowned for its medieval architecture and striking towers, which dominate the skyline. Visitors will enjoy a rich cultural experience with outdoor activities, family-friendly venues, and a variety of spas. The area is bustling with historic landmarks, including the famous Piazza della Cisterna and the Collegiata, both of which offer a glimpse into the town's storied past. Strolling through the narrow cobblestone streets, you'll find charming shops, local eateries, and theatres that showcase the region's artistic flair.
  • Castel San Gimignano: Located a short distance from the city centre, Castel San Gimignano is a picturesque village that captivates visitors with its romantic ambiance and cultural charm. This quaint village is ideal for those seeking entertainment and guided tours through its historic sites, such as the Palazzo Comunale and the lovely piazza. One can enjoy leisurely walks through the scenic countryside, taking in the breathtaking Tuscan landscapes, vineyards, and olive groves that surround the area, making it a perfect spot for a quiet day trip.
  • Ulignano: Nestled nearby, Ulignano offers a serene escape into the heart of Tuscany. This charming village is perfect for those looking to experience romance and outdoor adventures. Attractions include beautiful piazzas and historic monuments that tell the tales of the region's rich heritage. Visitors can indulge in spa treatments and theatre performances, making it an ideal destination for relaxation and entertainment. The surrounding tranquil countryside invites exploration, whether on foot or by bike, allowing you to soak in the stunning views and local charm.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Are you hoping to save some cash on your upcoming adventure? Being flexible with your travel dates can be a great way to take advantage of fluctuating prices. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, continue from where you last stopped, or easily review and organize your plans. You’ll discover your saved or booked properties neatly categorized into Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Head to the historic 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 accommodations with space to entertain friends and family, Vrbo 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 things to do in the area? Venture out of your cozy vacation rental and experience everything that makes San Gimignano a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 active traveler or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in San Gimignano. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Sentierelsa Trail (5.3 mi / 8.6 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)
  • Alta Val d'Elsa River Park (7.1 mi / 11.4 km)
  • Chianti Sculpture Park (17.7 mi / 28.5 km)

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 when booking a vacation rental?
Pancole is one of the more popular areas to book a Vrbo vacation 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 vacation rental accommodation in San Gimignano?
The most desirable types of vacation 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 vacation 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 vacation rental in San Gimignano?
Different factors affect how much you’ll pay for a vacation rental in San Gimignano, including the length of stay, season and type of property. But, all of our vacation 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 vacation home near the beach in San Gimignano depends on when you’re traveling 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 vacation rentals in San Gimignano?
Pack a suitcase and a bone for the pooch in your life because San Gimignano has 144 vacation 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 vacation 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 vacation 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 vacation rentals, you’ll have options to suit your taste and style, whether you’re traveling with your partner, your friends or even pets.
Are there large group vacation rentals in San Gimignano?
San Gimignano has 14 vacation 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 vacation rentals in San Gimignano that welcome kids?
San Gimignano has 142 family-friendly vacation 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 vacation rentals in San Gimignano?
There are 55 one-bedroom properties in San Gimignano to pick from. A one-bedroom vacation rental is an excellent choice if it’s just two of you or if you’re traveling 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 vacation rentals in San Gimignano?
Take off with your besties and experience complete comfort and privacy in one of the 41 two-bedroom vacation homes San Gimignano has to offer.
Are there vacation rentals with WiFi in San Gimignano?
San Gimignano has 72 vacation rentals with WiFi, so you can stay connected while traveling. 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 vacation rentals with air conditioning in San Gimignano?
Pick your travel dates and then use our filters to locate vacation 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 vacation 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 vacation home before booking your stay.
How long can I rent a vacation rental in San Gimignano for?
The amount of time you can book a San Gimignano vacation 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 vacation homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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