Monteriggioni holiday lettings

We found 2,734 holiday rentals — enter your dates for availability

Discover a selection of 35 apartments, 25 villas and other holiday rentals in Monteriggioni that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a fireplace. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Monteriggioni

Showing deals for:19 Jun - 26 Jun

Image gallery for FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!

Private swimming pool with breathtaking views over the typical Tuscan landscape
9.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)

FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!

Castellina in Chianti

9% off
Price is £8,359
for 7 nights, 1 villa
£1,194 per night
includes taxes & fees
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!

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Why visit Monteriggioni

  • Historic Monteriggioni Castle: Explore the impressive medieval fortress that offers stunning views and rich history.
  • Charming Walled Village: Wander through the picturesque streets of this well-preserved village, steeped in culture.
  • Scenic Outdoor Activities: Enjoy hiking in the surrounding countryside, perfect for nature enthusiasts.
  • Picturesque Piazza: Relax in the charming square, a lovely spot for leisurely strolls and local culture.
  • Variety of Accommodations: Choose from luxurious villas to cosy apartments for a personalised stay.

Popular types of accommodation in Monteriggioni

Discover the charm of Monteriggioni with our selection of holiday rentals, including stunning villas, inviting apartments, and private homes. Whether you're seeking a luxurious villa in Monteriggioni for a family getaway or a cosy apartment for a romantic escape, we have the perfect accommodation for you. Enjoy the beauty of this historic region while relishing the transparency, savings, and reassurance that comes with booking through our customer-centric platform.

  • Apartments: The top choice for accommodation in Monteriggioni, offering convenient and comfortable stays for solo travellers or couples.
  • Villas: A popular selection for those seeking luxury and space, perfect for families or larger groups.
  • Houses: Ideal for a home-from-home experience, providing privacy and flexibility during your stay.
  • Caravan Parks: A unique option for adventurous travellers, allowing you to immerse yourself in nature.
  • Cottages: Quaint and charming, these provide a delightful retreat for a peaceful getaway.**

Top attractions near Monteriggioni

Monteriggioni offers a charming mix of culture and romance, making it ideal for outdoor vacations. Visitors can explore notable attractions such as the stunning Monteriggioni Castle, the historic walled village, and the picturesque piazza. Outdoor enthusiasts will enjoy scenic hikes in the surrounding area, while families can immerse themselves in the rich local culture. This medieval gem caters to all types of travellers seeking a memorable Italian experience.

  • Siena Cathedral: This stunning cathedral, just 3.7km from Monteriggioni, is a masterpiece of Gothic architecture, featuring intricate frescoes and a breathtaking façade. Its rich cultural history and serene atmosphere provide a captivating experience for visitors.
  • Fortezza Medicea: A historic fortress located 3.7km away, this fort offers a glimpse into the past with its robust walls and fascinating history. The cultural vibes and scenic views from the ramparts make it a must-visit.
  • Piazza del Campo: Situated 4.3km from Monteriggioni, this iconic square is renowned for its unique shell shape and vibrant atmosphere. It hosts the famous Palio horse race, making it a lively cultural hub.

Things to do recommended for couples

For a romantic getaway in Monteriggioni, indulge in fine wines at Terra di Seta or Isole e Olena Winery, both exuding enchanting vibes. Enjoy a delightful meal at Frateria di Padre Eligio, perfect for couples seeking a warm atmosphere. Create unforgettable memories in this Tuscan gem!

Things to do recommended for families

Families exploring Monteriggioni can enjoy a thrilling day at the Siena Stadium, just 3.1km away, immerse themselves in the wonders of the Chianti Observatory 6.8km away, or experience the excitement of karting at the Siena Circuit, located 8.1km from the charming village.

Things to do recommended for groups

Explore the stunning Sentierelsa Trail for a scenic hike just 3.7km from Monteriggioni, then indulge in local wines at Enoteca Italiana. For a cultural touch, enjoy a performance at Teatro dei Rinnovati, located 4.3km away, perfect for family and romance.

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

If you're travelling with a group, family, pets, or seeking extended stays, it's essential to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Monteriggioni with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Fortunately, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Monteriggioni with young kids: Journeying with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monteriggioni: For many families, a holiday wouldn’t feel complete without their beloved pet. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Monteriggioni: If you're seeking holiday rentals with offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as 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 hilltop village in Tuscany, offers a delightful blend of culture, romance, and outdoor adventure. Visitors can immerse themselves in its rich history while enjoying stunning views of the surrounding countryside. The nearby towns provide a friendly atmosphere and picturesque scenery, making it an ideal destination for a relaxing holiday. Whether you seek luxury or seclusion, Monteriggioni promises an unforgettable experience in the heart of Tuscany.

  • Siena: Just 4.3km from Monteriggioni, Siena is a captivating city steeped in history and culture. Renowned for its stunning medieval architecture, the city is perfect for those seeking both outdoor adventures and romantic experiences. Stroll through the picturesque streets, enjoy the vibrant atmosphere of the Piazza del Campo, and indulge in rejuvenating spa treatments. Siena’s rich heritage is on display at its historic sites and museums, making it a must-visit for culture enthusiasts.
  • Abadia a Isola: Nestled within the Monteriggioni area, Abadia a Isola is a charming village that invites visitors to explore its serene landscapes and cultural treasures. Known for its outdoor activities and romantic ambiance, the village is home to an oasis, a historic castle, and a stunning palace that showcase the region's storied past. Whether you're seeking a peaceful retreat or a chance to immerse yourself in local history, Abadia a Isola offers a delightful experience.
  • Castellina Scalo: Located in close proximity to Monteriggioni, Castellina Scalo is a quaint village perfect for family outings and cultural explorations. With its historic buildings, majestic castle, and beautiful palace, this village is brimming with charm and character. Visitors can enjoy leisurely walks through the scenic surroundings, making it an ideal spot for those looking to create lasting memories with loved ones while soaking in the area's rich heritage.

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 holiday? It may be worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a dedicated space to plan new journeys, refine your existing arrangements, or review and manage your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting rustic Monteriggioni

The area's wineries and churches are just some of the reasons to come on holiday to 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 discover attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Monteriggioni has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Buondonno Winery (11.4 mi / 18.3 km)
  • Il Molino di Grace Winery (11.6 mi / 18.6 km)

Exploring the natural features in Monteriggioni

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Monteriggioni is a great place to spend some time outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (5.9 mi / 9.5 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)
  • Chianti Sculpture Park (8.3 mi / 13.4 km)
  • Val di Merse (13.2 mi / 21.3 km)

Transport to and around Monteriggioni

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

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 holiday rental?
When considering a holiday rental in Monteriggioni, a popular area to stay is the historic centre itself. This charming medieval village is renowned for its well-preserved walls and stunning views of the surrounding Tuscan countryside, making it a picturesque backdrop for your holiday. Within the walls, you'll find a variety of properties, ranging from cosy apartments to elegant villas, which offer a unique opportunity to immerse yourself in the local history.

Staying in the historic centre also places you close to key attractions such as the impressive Monteriggioni Castle, which is an absolute must-visit. The castle's ramparts provide breathtaking panoramic views and offer insight into the region's rich past. Additionally, the quaint streets are lined with delightful shops and eateries where you can savour traditional Tuscan cuisine.

Another appealing area is the outskirts of Monteriggioni, where you can enjoy more spacious properties set amidst rolling hills and vineyards. This setting allows for a tranquil escape while still being just a short distance from the village centre. The area is also known for its scenic walking and cycling paths, making it ideal for those who enjoy outdoor activities.
How much does it cost to rent a holiday home in Monteriggioni?
Prices for holiday 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 holiday 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 Monteriggioni ski resort rentals?
For those seeking ski resort rentals near Monteriggioni, the nearest options are available in the nearby area of Abetone, which is approximately a two-hour drive away. In Abetone, travellers can find a variety of accommodation types, including cosy chalets and modern apartments, many of which provide breathtaking views of the surrounding Apennine Mountains. These properties typically come with amenities such as well-equipped kitchens, comfortable living areas, and some even feature outdoor balconies or terraces for enjoying the alpine scenery.

In addition, Montagna Pistoiese, located close to Abetone, offers further rental opportunities in picturesque villages like Cutigliano and Piteglio. Here, guests can expect charming stone cottages or rustic wooden lodges, often boasting traditional Tuscan decor, fireplaces, and access to local hiking trails. Many of these rentals also provide convenient access to local shops and eateries, enhancing the overall experience for visitors looking to enjoy both skiing and the rich cultural heritage of the region.
What is the most popular type of holiday rental accomodation in Monteriggioni?
In Monteriggioni, apartments are the most popular type of holiday rental, with around 147 available throughout this charming medieval village. These apartments often feature traditional Tuscan decor, fully equipped kitchens, and comfortable living areas, providing a homey atmosphere for travellers. Many are situated near key attractions, such as the historic walls of Monteriggioni and the scenic countryside.

Additionally, there are approximately 72 villas available, which offer more spacious rooms for larger groups or families. These villas typically include multiple bedrooms, private gardens, and outdoor dining areas, making them great for enjoying the stunning Tuscan landscape. There are also about 54 holiday houses, which provide a similar spaciousness and home-like quality, ideal for those seeking a more secluded escape.
Are there any family house rentals in Monteriggioni?
In Monteriggioni, Tuscany, families will find a multitude of holiday rentals—approximately 67 options available throughout the area. The picturesque medieval village is surrounded by stunning countryside, making it an excellent choice for family getaways. Many of these homes feature spacious living areas, well-equipped kitchens for preparing meals together, and outdoor spaces superb for children to play or enjoy alfresco dining.

Visitors can explore the charming streets of Monteriggioni, with its historic walls and towers, while also being a short drive from attractions like the beautiful vineyards of Chianti and the art-rich city of Siena. Additional amenities often include Wi-Fi, air conditioning, and sometimes even swimming pools, ensuring a comfortable and enjoyable stay for families.
Can I rent a holiday home with a pool or hot tub in Monteriggioni?
In Monteriggioni, there are plenty of holiday homes available for rent with pools and hot tubs, with around 70 options to choose from. This picturesque medieval town in Tuscany is surrounded by stunning countryside and vineyards, making it a lovely destination for relaxation and exploration. Many of these properties feature private pools, some with stunning views of the rolling hills, as well as hot tubs for a touch of luxury after a day of sightseeing.

Travellers can expect amenities such as spacious living areas, fully equipped kitchens for preparing local Tuscan cuisine, and outdoor dining spaces great for enjoying al fresco meals.
Can I find long-stay holiday rentals in Monteriggioni?
A long-stay holiday rental in Monteriggioni is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Monteriggioni?
In Monteriggioni, there are numerous pet-friendly house rentals available, with around 62 options to choose from. This charming medieval village in Tuscany offers a picturesque setting, with holiday homes that often feature rustic decor, spacious gardens, and amenities such as fully equipped kitchens and outdoor dining areas. Many properties provide comfortable living spaces, ideal for families or groups travelling with pets.

The surrounding countryside is superb for exploring with your furry friends, as there are several walking trails that lead through the rolling hills and vineyards typical of the region. The nearby Val d'Elsa and the scenic Chianti area are also great for outdoor activities, making Monteriggioni an excellent base for those looking to enjoy both the beauty of Tuscany and the companionship of their pets.
Are there any remote work holiday rentals in Monteriggioni?
In Monteriggioni, Tuscany, there is a wide selection of remote work holiday rentals, with around 261 options available. This picturesque medieval village is not only steeped in history but also offers a tranquil environment ideal for working remotely. Many properties feature essential amenities such as free Wi-Fi, ensuring that guests can stay connected during their stay.

Accommodations often include spacious living areas that can be converted into comfortable workspaces, alongside fully equipped kitchens for convenient meal preparation. Some rentals may also allow for events, making them suitable for small gatherings or meetings.

The charming surroundings of Monteriggioni provide ample opportunities for relaxation after work, with stunning views of the Tuscan countryside and easy access to local attractions, such as the nearby vineyards and historic sites. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monteriggioni holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Monteriggioni with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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, holiday rentals often come equipped with a range of desirable amenities that enhance the overall experience. Most properties feature well-appointed kitchens, allowing guests to prepare their own meals using fresh local ingredients. Onsite parking is commonly available, making it convenient for those travelling by car. Many rentals also permit pets, suiting those who wish to bring their furry companions along. Outdoor spaces such as gardens and decks or patios are typical, providing lovely areas to relax and enjoy the beautiful Tuscan countryside.
When is the best time to visit Monteriggioni for a holiday rental?
September is the most popular time to visit Monteriggioni, as the summer crowds begin to disperse, yet the warm Tuscan sun still bathes the landscape in golden hues. This month is particularly appealing to travellers seeking a blend of cultural exploration and outdoor activities, with comfortable temperatures averaging around 20 to 25 degrees Celsius. It's ideal for leisurely strolls through the medieval streets, enjoying the local cuisine at outdoor cafes, and participating in the numerous harvest festivals that celebrate the region's rich agricultural heritage.

The peak season in Monteriggioni runs from August to October, with August being the busiest month. During this time, the charming village comes alive with tourists drawn to its historical sites and stunning views. The atmosphere is vibrant, and there's plenty of opportunity for sightseeing, from the impressive fortress walls to nearby vineyards offering tastings.

For those who appreciate a quieter experience, February is a great time to consider a holiday rental. The village is less crowded, allowing for a more intimate exploration of its narrow streets and hidden gems, all while enjoying the serene beauty of the Tuscan countryside. While temperatures can be cooler, ranging from 0 to 10 degrees Celsius, the crisp air adds a refreshing touch to your outdoor adventures.

Ultimately, whether you prefer the bustling charm of September or the tranquillity of February, Monteriggioni offers great experiences that cater to a variety of travel preferences.
How early should I book a Monteriggioni holiday rental?
Book your Monteriggioni holiday 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 holiday 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 engage in a rich tapestry of history and stunning scenery. The medieval walls of Monteriggioni are a significant attraction, providing panoramic views of the surrounding Tuscan countryside. Within the walls, the charming piazza is lined with traditional shops and cafes, great for experiencing local cuisine and culture.

The Church of Santa Maria Assunta, located in the heart of the village, showcases beautiful artwork and offers a glimpse into the area's religious heritage. For those interested in outdoor activities, the surrounding landscape is ideal for hiking and cycling, with several trails leading through the picturesque hills.

Additionally, Monteriggioni serves as a great base for exploring nearby attractions such as the famous Chianti wine region, and the historic cities of Siena and San Gimignano, both of which are just a short drive away.
Can I change or cancel my Monteriggioni home rental booking on Vrbo?
To find Monteriggioni holiday 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 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 travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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