Monteriggioni vacation rentals

We found 2,621 vacation rentals — enter your dates for availability

Discover a selection of 18 homes, 41 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:Apr 17 - Apr 24

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

Villa Simo
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 $602
$4,217 for 7 nights
All fees included
Villa with private pool on 25 acres in the heart of Chianti, close to Siena

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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)
  • Sovestro in Poggio Winery (10.3 mi / 16.6 km)
  • Casa Sola - Chianti Winery (10.8 mi / 17.4 km)
  • Buondonno Winery (11.4 mi / 18.3 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)
  • 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)
  • Val di Merse (13.2 mi / 21.3 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 when booking a vacation rental?
When planning a vacation in Monteriggioni, one of the best areas to consider for your rental is the historic center. This charming area is renowned for its medieval architecture and stunning views of the surrounding Tuscan countryside. Staying in the heart of Monteriggioni allows you to easily explore top attractions such as the well-preserved walls of the fortress and the picturesque Church of Santa Maria Assunta, both of which are steeped in history and offer fantastic photo opportunities.

Another appealing option is the outskirts of the town, where you can find a range of vacation rentals set amidst beautiful vineyards and olive groves. This area provides a peaceful retreat while still being a short distance from the center. It's great for those who want to enjoy nature and tranquility while being close enough to visit local attractions like the Monteriggioni Castle and the nearby Chianti wine region.

In both areas, you can find a variety of rental properties, from quaint apartments to spacious villas, making it easy to find the great fit for your vacation.
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, Tuscany, Italy, travelers may want to explore the nearby coastal areas along the Tuscan coastline, particularly around the charming town of Castiglione della Pescaia, which is approximately a 45-minute drive from Monteriggioni. This picturesque area offers beautiful sandy beaches and a variety of beach houses that cater to different group sizes. Many rentals feature amenities such as private terraces with sea views, outdoor dining spaces, and easy access to the beach, making them ideal for enjoying the Mediterranean climate.

Additionally, the coastal town of Punta Ala is another excellent option, known for its upscale atmosphere and stunning beaches. Beach houses here often provide luxurious amenities, including private pools, well-equipped kitchens, and proximity to both the beach and local restaurants. The area is also favored for its sailing opportunities and scenic walking paths along the shoreline.

For those looking for a blend of beach and cultural experiences, the nearby town of Forte dei Marmi offers vibrant beach clubs and a lively atmosphere, with rentals often featuring modern decor, air conditioning, and outdoor lounges. Visitors can enjoy local shops, fine dining, and cultural attractions, enhancing their stay in this beautiful part of Tuscany.
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 53 available throughout the picturesque town. These rooms often feature fully equipped kitchens, cozy living areas, and access to shared outdoor spaces, allowing guests to enjoy the Tuscan ambiance. Many are located near key attractions like the medieval walls and nearby vineyards, making them ideal for travelers seeking both comfort and convenience.

For those looking for more space, approximately 23 villas are also available, providing luxurious amenities such as private pools, expansive gardens, and stunning views of the surrounding countryside. Additionally, there are around 17 vacation houses, which offer spacious layouts suitable for families or groups, often including barbecue facilities and outdoor dining areas for enjoying the beautiful Tuscan weather.
Are there any family house rentals in Monteriggioni?
In Monteriggioni, Tuscany, there is a substantial selection of family-friendly homes available, with around 63 options to choose from. This charming medieval village is surrounded by stunning landscapes and historical sites, making it an excellent choice for families. Many properties offer spacious living areas, well-equipped kitchens for preparing family meals, and outdoor terraces or gardens where children can play safely.

Visitors can enjoy proximity to attractions such as the ancient walls of Monteriggioni, which provide a fascinating glimpse into the area's history, as well as nearby vineyards and olive groves that invite exploration. The region is also known for its scenic walking and biking trails, great for family outings.
Can I rent a vacation home with a pool or hot tub in Monteriggioni?
In Monteriggioni, there are many vacation homes available for rent that feature pools and hot tubs, with around 67 options to select from. This picturesque medieval town in Tuscany is surrounded by stunning landscapes and offers a rich historical atmosphere. Travelers can find a variety of accommodations, from charming villas to rustic farmhouses, each equipped with amenities such as private swimming pools, hot tubs, and spacious outdoor areas great for relaxation and leisure.

Many properties also include fully equipped kitchens, allowing guests to prepare meals using local ingredients, and comfortable living spaces for family gatherings. Some of the rentals may feature terraces with panoramic views of the Tuscan hills, making them ideal for enjoying the serene environment. Monteriggioni's proximity to attractions like vineyards, olive groves, and other medieval towns enhances the experience, providing plenty of opportunities for exploration and cultural immersion.
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 can find an impressive selection of pet-friendly house rentals, with around 64 options available to choose from. This charming medieval village in Tuscany is known for its stunning landscapes and historical significance, making it an attractive destination for both travelers and their furry companions. The vacation rentals in the area often come equipped with amenities such as private gardens, outdoor dining areas, and fully equipped kitchens, providing a comfortable setting for families or groups.

Many of these properties are situated near picturesque walking trails that wind through the countryside, allowing for enjoyable outings with pets. Additionally, the surrounding region offers several pet-friendly points of interest, such as the scenic vineyards and olive groves that characterize the Tuscan landscape.
Are there any remote work vacation rentals in Monteriggioni?
In Monteriggioni, Tuscany, there are a variety of vacation rentals that cater to remote work needs, with about 87 options available. This picturesque medieval village offers a serene environment ideal for productivity, surrounded by stunning landscapes and rich history. Many properties feature dedicated office spaces equipped with desks and ergonomic chairs, along with reliable Wi-Fi to ensure seamless connectivity.

Guests can expect amenities like safe storage for valuable items, laptop-compatible safes, and even computer monitors in some rentals, making it easy to set up a comfortable workspace. Additionally, the charm of Monteriggioni includes historical sites, beautiful countryside for breaks, and local eateries where you can enjoy authentic Tuscan cuisine. 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 WiFi, kitchens, and shared pools, suiting the needs of travelers seeking both connectivity and comfort during their stay. Many rentals offer a coffee and tea maker, allowing guests to enjoy warm beverages at their leisure.
When is the best time to visit Monteriggioni for a vacation rental?
September is the most popular time to visit Monteriggioni, as the summer crowds begin to taper off while the weather remains pleasantly warm. This month is particularly appealing for travelers who appreciate a blend of cultural exploration and outdoor activities, set against the picturesque backdrop of Tuscany's rolling hills and historic architecture.

From August through October, Monteriggioni experiences its peak season, drawing visitors eager to enjoy the local harvest festivals and the stunning landscapes. During this period, temperatures typically range from the mid-60s to the low 80s Fahrenheit, creating ideal conditions for sightseeing and leisurely strolls through the charming medieval village. The vibrant autumn foliage enhances the scenery, making it a great time for photographers and nature lovers alike.

For those looking for a more budget-friendly option, February offers a wonderful opportunity to experience Monteriggioni in a quieter setting. While the temperatures can be cooler, ranging from the low 30s to mid-50s Fahrenheit, visitors can enjoy a more intimate atmosphere and have the historical sites largely to themselves. This month allows you to savor local cuisine and the cozy ambiance of the region without the crowds.

Ultimately, your best time to book a vacation rental in Monteriggioni depends on your preferences. If you're seeking lively events and a bustling atmosphere, September will meet your needs beautifully. However, if you prefer a tranquil experience rich in local culture, consider planning your visit in February.
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?
In Monteriggioni, visitors can take part in the charm of this medieval walled town, famous for its well-preserved fortress walls and towers. The central square, Piazza Roma, is a key attraction where travelers can enjoy local cafes and shops while soaking in the historic atmosphere. The town's medieval architecture, including the Church of Santa Maria Assunta, offers a glimpse into its rich history.

For those interested in scenic views, the surrounding countryside provides beautiful landscapes typical of Tuscany, making it a great backdrop for leisurely strolls or bike rides. Additionally, Monteriggioni is conveniently located near the famous Chianti wine region, allowing for wine tasting tours and exploration of vineyards.
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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