Monteriggioni vacation rentals

We found 2,705 vacation rentals — enter your dates for availability

Discover a selection of 23 homes, 33 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:Jul 3 - Jul 10

Image gallery for Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views

Villa Patrignone from the rear
9.4 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views

Barberino Tavarnelle

12% off
Price is $684
$4,789 for 7 nights
All fees included
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views

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Find out more about Monteriggioni

Why visit Monteriggioni

  • Historic Castle: Explore the well-preserved medieval castle that offers a glimpse into Monteriggioni's rich history.
  • Stunning Scenery: Enjoy breathtaking views of the Tuscan countryside, making it a perfect spot for photography and relaxation.
  • Picturesque Streets: Wander through charming streets and piazzas filled with local shops and cafes.
  • Cultural Experiences: Discover local museums and immerse yourself in the vibrant culture of this quaint town.
  • Diverse Accommodations: Choose from a range of options, including charming apartments and luxurious villas for a memorable stay.

Popular types of accommodation in Monteriggioni

If you're looking for the perfect getaway in Monteriggioni, you're in the right place. Our most popular vacation rental options include charming apartments, luxurious villas, and inviting houses. Whether you're interested in exclusive Monteriggioni villa rentals or the historic charm of Palazzo Monteriggioni, we have a variety of holiday villas to suit your needs. Enjoy your stay with transparency and savings, knowing you'll find the ideal accommodation for your adventure.

  • Apartments: The top choice for travelers in Monteriggioni, offering a comfortable and convenient stay with home-like amenities.
  • Villas: These luxurious properties provide spacious accommodations and stunning views, perfect for indulgent getaways.
  • Houses: Ideal for families or groups, these homes offer privacy and a personal touch during your stay.
  • Caravan Parks: A unique experience for those seeking adventure, combining outdoor living with community amenities.
  • Cottages: Quaint and cozy, these charming retreats are perfect for a peaceful escape in the countryside.**

Top attractions in and around Monteriggioni

Monteriggioni, a charming Tuscan destination, is perfect for romantic and culture-themed vacations. Explore its medieval castle, picturesque piazzas, and local museums. The area offers rich cultural experiences for families and travelers alike, with attractions such as the renowned Chianti Hills. Don't miss the opportunity to soak in the town's history and stunning scenery, making it an ideal spot for an unforgettable getaway.

  • Monteriggioni Castle: This historic castle features well-preserved walls and towers, offering a glimpse into medieval life. Wander through its charming streets and soak up the cultural atmosphere that permeates this quaint village.
  • Piazza del Campo: Renowned for its distinctive shell shape, this vibrant square is the heart of Siena, just 7 miles away. Enjoy local cuisine at cafés, admire stunning architecture, and experience the lively ambiance during events.
  • Fortezza Medicea: A historic fortress that reflects Renaissance military architecture, located 6 miles from Monteriggioni. Explore its expansive grounds and enjoy panoramic views of the surrounding landscape steeped in history.

Things to do recommended for couples

For a romantic getaway in Monteriggioni, consider visiting the luxurious Villa a Sesta Polo Club, located 17 miles away. Enjoy the serene countryside, indulge in fine dining, and experience the exclusive atmosphere perfect for couples seeking a memorable escape together.

Things to do recommended for families

Your family can explore the medieval walls of Monteriggioni, discovering its fascinating history. Enjoy a picnic in the scenic surroundings, and visit local shops for handmade crafts. Don't miss the chance to savor delicious gelato from a nearby café, making sweet memories together in this charming village.

Things to do recommended for groups

Groups visiting Monteriggioni can enjoy a guided tour of the medieval fortress, savor wine tastings at local vineyards, and participate in a traditional Tuscan cooking class. Don't miss a scenic walk along the ancient walls for breathtaking views of the beautiful countryside.

*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

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Monteriggioni 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. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Monteriggioni with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming 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. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Monteriggioni: If you're in search of vacation rentals that offer great deals for stays of a month or longer, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Monteriggioni

Monteriggioni, a charming Tuscan gem, offers a romantic escape with its stunning views of the surrounding countryside. Travelers can explore historic Italian villas near Siena and enjoy the relaxing atmosphere of this quaint town. With friendly locals and a rich cultural vibe, Monteriggioni is perfect for those seeking adventure or luxury. Don't miss the opportunity to wander through its picturesque streets and soak in the breathtaking scenery that defines the heart of Tuscany.

  • Siena: Siena is a historic city located approximately 7 miles from Monteriggioni, known for its rich culture and stunning medieval architecture. Visitors flock to Siena for its vibrant outdoor activities and romantic ambiance. The city is famous for its beautiful piazza, Piazza del Campo, which hosts the thrilling Palio horse race twice a year. You can indulge in rejuvenating spa treatments or explore local museums that offer insight into Siena's fascinating history. Don't miss the chance to wander through its narrow streets, lined with charming shops and cafes, making it an ideal spot for both culture enthusiasts and leisurely strolls.
  • Strove: Nestled in the vicinity of Monteriggioni, Strove is a quaint village that offers a serene escape for travelers seeking a romantic and entertaining experience. The village is known for its picturesque landscapes and proximity to historic landmarks, including a charming castle and natural hot springs. Visitors can enjoy relaxing body treatments and spa experiences, making it a perfect destination for rejuvenation. The rich history of Strove, combined with its tranquil atmosphere, allows visitors to immerse themselves in the beauty of Tuscany's countryside while enjoying leisurely outdoor pursuits.
  • Castellina Scalo: Castellina Scalo is a delightful village close to Monteriggioni, attracting those looking for a blend of culture and romance. This charming locale features stunning historical palaces and a picturesque piazza, providing a perfect backdrop for exploring Tuscany's heritage. The village is an excellent base for visiting nearby castles and enjoying the scenic beauty of the region. With its inviting atmosphere and cultural richness, Castellina Scalo offers a unique experience for travelers who appreciate both the allure of city life and the tranquility of rural settings.

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 simple

Are you interested in saving money on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the best deal.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your existing plans, and review your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: 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:

  • Val di Merse (13.2 mi / 21.3 km)
  • Terme Antica Querciolaia (20.1 mi / 32.4 km)
  • Hedonistic Hiking (4 mi / 6.4 km)
  • Alta Val d'Elsa River Park (4.5 mi / 7.3 km)
  • Sentierelsa Trail (5.9 mi / 9.5 km)
  • Chianti Sculpture Park (8.3 mi / 13.4 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.

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