Monteriggioni vacation rentals

We found 2,745 vacation rentals — enter your dates for availability

Discover a selection of 18 homes, 35 apartments, and other vacation rentals in Monteriggioni that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for spending time at your vacation home, which might include parking and a fireplace. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Monteriggioni

Showing deals for:May 22 - May 29

Image gallery for Villa with private pool on 25 acres in the heart of Chianti, close to Siena

9.8 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Pievasciata

9% off
Price is $420
$2,943 for 7 nights
All fees included
Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Monteriggioni

Why visit Monteriggioni

  • Historic Walls: Explore the well-preserved medieval walls surrounding Monteriggioni, a true testament to its rich history.
  • Charming Piazzas: Enjoy the lively atmosphere of the village's piazzas, perfect for relaxing and soaking in local culture.
  • Cultural Experiences: Visit beautiful churches and engaging museums that showcase the area's artistic heritage.
  • Stunning Scenery: Take in breathtaking views of the Chianti vineyards and surrounding landscapes that define Tuscany.
  • Cozy Accommodations: Choose from a variety of charming apartments and luxurious villas for a memorable stay.

Popular types of accommodation in Monteriggioni

If you're considering a getaway to Monteriggioni, you'll find a variety of fantastic vacation rentals to suit your needs. Our most popular options include charming apartments, luxurious villas, and cozy houses. Whether you're searching for Monteriggioni villa rentals or the best villas in Monteriggioni, we have the perfect accommodations to ensure a memorable stay. Explore the beauty of this enchanting destination with confidence, knowing you have the best options at your fingertips.

  • Apartments: The top choice for vacationers in Monteriggioni, offering convenience and comfort in a stylish setting.
  • Villas: A luxurious option that provides spacious accommodations and beautiful surroundings, perfect for families or groups.
  • Houses: Ideal for those seeking a home-like atmosphere, allowing for privacy and personalized experiences.
  • Caravan Parks: A unique way to enjoy the outdoors, combining camping with essential amenities for a fun-filled stay.
  • Cottages: Quaint and charming, these intimate spaces are perfect for a romantic getaway or a peaceful retreat.**

Top attractions in and around Monteriggioni

Monteriggioni, a charming Tuscan village, is perfect for culture, romance, and outdoor adventures. Explore its beautiful churches, lively piazzas, and engaging museums. Don't miss excursions from Monteriggioni to nearby attractions, and take time to admire the historic walls that surround this walled gem. Ideal for families and culture enthusiasts alike, Monteriggioni offers a rich experience of Italian heritage and scenic landscapes.

  • Piazza del Campo: This iconic square, located 7 miles from Monteriggioni, is renowned for its unique shell shape and vibrant atmosphere. It serves as the heart of Siena, where locals and tourists gather to enjoy the rich culture, historic events, and lively outdoor cafes.
  • Siena Cathedral: Situated 6 miles away, this stunning cathedral showcases breathtaking Gothic architecture and intricate artwork. Visitors can explore its magnificent interior and climb to the panoramic viewpoint for a spectacular view of Siena.
  • Monteriggioni Castle: Nestled within Monteriggioni, this historic castle boasts impressive medieval walls and towers. Experience the charm of this small village while walking along the ramparts and soaking in the surrounding Tuscan landscape.

Things to do recommended for couples

For a romantic getaway in Monteriggioni, visit Terra di Seta Winery for enchanting wine experiences just 5 miles away, dine at Frateria di Padre Eligio, 7 miles from town, for a cozy meal, and savor the romantic ambiance at Isole e Olena Winery, located 10 miles away.

Things to do recommended for families

Families can enjoy a thrilling day at the Siena Circuit for karting adventures, just 13 miles away. For sports enthusiasts, the nearby Siena Stadium and Palasport Mens Sana, both 5 miles away, offer exciting events and a lively atmosphere perfect for all ages.

Things to do recommended for groups

In Monteriggioni, your group can hike the scenic Sentierelsa Trail for outdoor adventure, visit the charming Enoteca Italiana for local wines, and enjoy a cultural performance at Teatro dei Rinnovati, perfect for family fun and romantic evenings.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you’re planning a trip with friends, family, pets, or if you're considering an extended stay, be sure to prioritize your preferences while filtering your options. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Monteriggioni with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Monteriggioni with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monteriggioni: For many families, a trip isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Monteriggioni: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Monteriggioni

Monteriggioni, a charming Tuscan gem, offers a delightful blend of culture, romance, and outdoor adventure. Explore beautiful villas and luxury homes with stunning views, set against the backdrop of Chianti vineyards. Whether you're seeking a secluded retreat or a friendly atmosphere, you'll find plenty to enjoy in this historical town and its picturesque surroundings. Immerse yourself in the enchanting scenery and experience the warm hospitality of the locals during your vacation.

  • Siena: Located 7 miles from Monteriggioni, Siena is a captivating city renowned for its rich history and vibrant culture. Travelers flock to Siena for an immersive experience filled with outdoor activities and romantic settings. As you stroll through its medieval streets, be sure to visit the stunning Piazza del Campo, where the famous Palio horse race takes place. The city is also home to remarkable landmarks such as the Siena Cathedral and the Palazzo Pubblico. For relaxation, indulge in local spa treatments and body therapies that promise rejuvenation after a day of exploration.
  • Castellina Scalo: Nestled in the Monteriggioni area, Castellina Scalo is a charming village that offers a quaint escape for families and couples alike. Visitors are drawn to its culture-themed attractions, including ancient castles and historic palaces that tell stories of the region's past. The village exudes a romantic atmosphere, making it perfect for leisurely strolls. Don't miss the opportunity to explore nearby monuments that showcase the rich heritage of Tuscany and provide stunning backdrops for memorable photographs.
  • Badesse: Just a stone's throw from Monteriggioni, Badesse is a picturesque village that invites travelers to delve into its cultural treasures. While it may be less commercialized, Badesse boasts significant landmarks such as ancient monasteries and places of worship that reflect its historical importance. Explore the captivating ruins that whisper tales of yesteryears, providing a serene setting for reflection and discovery. Whether you're seeking spirituality or simply a quiet retreat, Badesse offers a unique experience off the beaten path.

Best time to go to Monteriggioni

If you're planning a trip to Monteriggioni, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyLowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyLowSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnyHighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyHighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyHighAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo rental that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Planning really does have its perks. When you join our travel rewards program, One Key, you’ll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for planning your next adventures, allowing you to easily start new trips, resume previous ones, or manage your travel arrangements all in one place. You'll be able to see your saved or booked properties neatly organized under categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting rustic Monteriggioni

The area's wineries and churches are just a few of the reasons to vacation in Monteriggioni. One of the city's many top draws is its local tours. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Monteriggioni

Do you want to find attractions to visit while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Monteriggioni a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Castello di Monsanto (8.9 mi / 14.3 km)
  • Castello della Paneretta (9.2 mi / 14.8 km)
  • Isole e Olena Winery (9.7 mi / 15.6 km)
  • Casa Emma (10.3 mi / 16.5 km)
  • Sovestro in Poggio Winery (10.3 mi / 16.6 km)
  • Casa Sola - Chianti Winery (10.8 mi / 17.4 km)

Exploring the natural features in Monteriggioni

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Monteriggioni is a great place to get out in nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Chianti Sculpture Park (8.3 mi / 13.4 km)
  • Val di Merse (13.2 mi / 21.3 km)
  • Terme Antica Querciolaia (20.1 mi / 32.4 km)
  • Alta Val d'Elsa River Park (4.5 mi / 7.3 km)
  • Le Caldane Thermal Baths (4.6 mi / 7.3 km)
  • Sentierelsa Trail (5.9 mi / 9.5 km)

Transportation to and around Monteriggioni

Fly into Florence Airport, Peretola (FLR), the closest airport, located 30 mi (48.3 km) from the city center.

If you prefer train travel, make your way to Monteriggioni Castellina Station or Monteriggioni Badesse Station to see more of the city.

Frequently asked questions

What is the best area to stay in Monteriggioni, Tuscany, Italy when booking a vacation rental?
When booking a vacation rental in Monteriggioni, Tuscany, one of the best areas to consider is the charming historic center. This area is renowned for its well-preserved medieval walls and picturesque streets, offering a truly authentic Tuscan experience. Staying here allows easy access to attractions such as the impressive Monteriggioni Castle, which provides stunning views of the surrounding countryside, and the nearby Church of Santa Maria Assunta, known for its beautiful artwork and historical significance.

Additionally, the area surrounding the historic center is dotted with lovely vineyards and olive groves, great for leisurely strolls or bike rides. There are a variety of properties available in this area, from cozy apartments to luxurious villas, suiting different tastes and budgets.
How much does it cost to rent a vacation home in Monteriggioni?
Prices for vacation rentals in Monteriggioni 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 Monteriggioni 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 Monteriggioni vacation house rentals?
You can find great discounts on house rentals in Monteriggioni 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 Monteriggioni?
For renting a beach house in Monteriggioni, travelers should explore the nearby coastal areas of Tuscany, particularly the stunning beaches along the Tyrrhenian Sea. The closest beach town to Monteriggioni is Castiglione della Pescaia, known for its beautiful sandy shores and crystal-clear waters. Here, visitors can find a variety of vacation rentals, including beachfront villas and charming cottages that often feature amenities like terraces with sea views, private pools, and outdoor dining areas, superb for enjoying the pleasant Tuscan climate.

Additionally, the coastal area around San Vincenzo offers more options, where properties typically include modern conveniences such as fully equipped kitchens, spacious living areas, and easy access to the beach. These rentals may also provide family-friendly amenities like gardens and proximity to local markets and restaurants, enhancing the overall beach experience.

For travelers seeking a blend of beach and cultural exploration, the nearby town of Follonica is also worth considering. Rentals here often offer amenities like air conditioning, balconies, and communal pools, alongside access to vibrant beachfront promenades and local dining options.
What is the most popular type of vacation rental accomodation in Monteriggioni?
In Monteriggioni, apartments are the most popular type of vacation rental, with about 49 available throughout the charming medieval town. These apartments are often located within historic buildings, providing travelers with a unique blend of modern amenities and traditional Tuscan architecture. Most units come equipped with fully stocked kitchens, cozy living areas, and some even feature picturesque views of the surrounding countryside.

For those seeking more space, there are approximately 24 villas available, which typically include multiple bedrooms, private gardens, and outdoor terraces ideal for enjoying the beautiful Tuscan landscape. Additionally, around 18 vacation houses and several cottages provide options for families or groups wanting a more secluded stay. These rentals often boast additional amenities like BBQ areas and spacious dining areas, making them great for gatherings.
Are there any family house rentals in Monteriggioni?
In Monteriggioni, Tuscany, there are numerous family-friendly houses available, with around 67 options to choose from. This charming medieval village offers various properties that cater to families, often featuring spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces ideal for children to play. Many rentals come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all.

Visitors can explore the enchanting surroundings, which include beautiful vineyards and olive groves. The nearby towns of Siena and San Gimignano provide rich cultural experiences, with their historic architecture and vibrant local markets. See all family-friendly rentals in Monteriggioni.
Can I rent a vacation home with a pool or hot tub in Monteriggioni?
In Monteriggioni, Tuscany, there are approximately 70 vacation homes available for rent that feature pools or hot tubs, providing a great selection for travelers looking to enjoy a refreshing dip or unwind in a hot tub. The charming medieval village is surrounded by beautiful landscapes, and many properties offer scenic views of the rolling Tuscan hills.

Travelers can expect a range of amenities, including private swimming pools, outdoor dining areas, and fully equipped kitchens superb for preparing local Tuscan dishes. Some rentals may also have additional features like spacious gardens, barbecue areas, and terraces for al fresco dining, enhancing the overall experience of relaxation and enjoyment in this picturesque setting.
Can I find long-stay vacation rentals in Monteriggioni?
A long-stay vacation rental in Monteriggioni is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Monteriggioni?
In Monteriggioni, travelers will find a variety of pet-friendly house rentals available, with around 62 options to choose from. Many of these accommodations are situated in picturesque settings, featuring traditional Tuscan architecture and modern amenities. Expect to find properties equipped with full kitchens, spacious living areas, and outdoor spaces where pets can enjoy the beautiful Tuscan landscape.

The area is rich in history and charm, with the medieval fortress of Monteriggioni being a significant point of interest, offering scenic walks and exploration opportunities. Nearby, travelers can discover lovely vineyards and olive groves, ideal for leisurely strolls with pets. In addition, there are several parks and open areas in the vicinity that welcome dogs, allowing for enjoyable outdoor activities.
Are there any remote work vacation rentals in Monteriggioni?
In Monteriggioni, travelers seeking remote work vacation rentals will find a variety of options, with approximately 87 properties available. This picturesque medieval town in Tuscany offers a charming backdrop for those looking to balance work and leisure. Many rentals come equipped with essential amenities such as free Wi-Fi in rooms, public areas, and desks, ensuring a comfortable and productive workspace.

Visitors can expect features like laptop-compatible safes and convenient internet services, allowing for seamless connectivity. The historical ambiance of Monteriggioni, with its ancient walls and scenic views of the surrounding countryside, provides a serene environment for remote work. Additionally, the proximity to local attractions, such as the nearby Chianti vineyards and the beautiful landscapes of Tuscany, allows for enjoyable breaks after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monteriggioni vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Monteriggioni with parking available—perfect for families or travelers 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 Monteriggioni?
In Monteriggioni, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare meals with local ingredients. Onsite parking is commonly available, making it convenient for travelers with vehicles. Many rentals are pet-friendly, accommodating those who wish to bring their furry companions along. Additionally, guests can enjoy outdoor spaces such as gardens and decks or patios, great for relaxing and taking in the beautiful Tuscan scenery.
When is the best time to visit Monteriggioni for a vacation rental?
September is the most popular time to visit Monteriggioni, a charming medieval village in Tuscany, offering a blend of history and stunning landscapes. During this month, the weather is typically warm and pleasant, with temperatures ranging from the mid-60s to mid-80s Fahrenheit, making it ideal for outdoor activities such as exploring the ancient walls or wandering through the picturesque vineyards.

The peak season in Monteriggioni spans from August to October, attracting a lively influx of tourists eager to experience the Tuscan countryside's beauty and partake in local festivals. This period is great for those who appreciate the vibrant setting that accompanies community events, including food fairs showcasing the region's culinary delights.

For travelers looking for a more budget-friendly option, consider planning your visit in February. While this month sees fewer tourists, it offers unique opportunities for a cozy retreat, where you can enjoy the tranquil charm of Monteriggioni and take in the serene winter landscape. The quiet ambiance allows for leisurely exploration of the village's historic sites and nearby attractions without the crowds.

Ultimately, the best time to book your vacation rental in Monteriggioni depends on your preferences—whether you desire the bustling energy of peak season or the peacefulness of the quieter winter months.
How early should I book a Monteriggioni vacation rental?
Book your Monteriggioni vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Monteriggioni, Tuscany, Italy?
In Monteriggioni, visitors can take part in the rich history and stunning architecture of this medieval walled town. The iconic walls and towers, which date back to the 13th century, offer breathtaking views of the surrounding Tuscan countryside, making for a picturesque backdrop. Within the walls, you can explore the charming narrow streets lined with local shops and cafes, where you can sample regional delicacies.

One of the main attractions is the Church of Santa Maria Assunta, known for its beautiful interior and historical significance. The town also hosts the Monteriggioni in Festa, a lively medieval festival that attracts many visitors each summer, showcasing local traditions, food, and entertainment.
Can I change or cancel my Monteriggioni home rental booking on Vrbo?
To find Monteriggioni vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Monteriggioni vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas