Monteriggioni holiday lettings

We found 2,727 holiday rentals — enter your dates for availability
Discover a selection of 22 homes, 33 apartments 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:9 Oct - 16 Oct

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

10% off
Price is £3,560
for 7 nights, 1 villa
£509 per night
includes taxes & fees
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views

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Why visit Monteriggioni

  • Medieval Architecture: Wander through Monteriggioni's ancient walls and cobbled streets, marveling at its stunning medieval architecture.
  • Scenic Views: Enjoy breathtaking panoramas of the surrounding Chianti hills, perfect for photography and relaxation.
  • Cultural Insights: Visit the local museum to delve into the rich history and heritage of the region.
  • Wine Tasting: Savor the local Chianti wines while exploring nearby vineyards.
  • Tranquil Atmosphere: Experience the peaceful charm of this enchanting town, ideal for a relaxing getaway.

Popular types of accommodation in Monteriggioni

Monteriggioni, nestled in the heart of Tuscany, boasts stunning medieval architecture and enchanting landscapes. Visitors can explore its impressive fortified walls, stroll through charming cobbled streets, and revel in breathtaking views of the surrounding countryside. For your stay, Monteriggioni offers a variety of vacation rentals, including beautiful villas, spacious apartments, and private homes, ensuring a perfect retreat. Whether you seek luxury or rustic charm, you'll find the best Monteriggioni villas to create unforgettable memories.

  • Apartments: These are the top choice for visitors, offering convenient and comfortable living spaces in Monteriggioni.
  • Villas: A popular option for those seeking luxury and privacy, villas provide ample space and beautiful surroundings.
  • Houses: Ideal for families or groups, these homes offer a homely atmosphere with the comforts of self-catering.
  • Caravan Parks: Great for a unique experience, caravan parks allow you to enjoy nature while having modern amenities.
  • Cottages: Charming and quaint, cottages offer a cosy retreat in the heart of Tuscany.**

Top attractions in and around Monteriggioni

Monteriggioni, a charming medieval walled town in Tuscany, offers a delightful blend of romantic and cultural experiences. Explore its historic castello and the impressive walls that encircle the town, or unwind in the picturesque piazza. With top hiking trails nearby, visitors can enjoy stunning views of the Tuscan landscape. The local museum provides insights into the region's rich history, making Monteriggioni an enchanting destination for families and culture enthusiasts alike.

  • Monteriggioni Castle: This historic castle is a stunning example of medieval architecture, surrounded by well-preserved walls and towers. Visitors can enjoy breathtaking views of the surrounding countryside while immersing themselves in the rich history and culture of the area.
  • Piazza del Campo: Although located 11km away, this iconic square is renowned for its unique shell shape and vibrant atmosphere. It is the heart of Siena's cultural life, hosting events and gatherings throughout the year.
  • Fortezza Medicea: Situated 10km away, this historic fortress offers an insight into the region's past, with impressive architecture and beautiful gardens that invite exploration and relaxation.

Things to do recommended for couples

Monteriggioni offers a charming getaway for couples. Wander hand-in-hand along the ancient walls, savour a candlelit dinner at a local trattoria, and enjoy a wine tasting at a nearby vineyard. The picturesque views and tranquil atmosphere make it an idyllic setting for romance.

Things to do recommended for families

Families visiting Monteriggioni can explore the enchanting medieval walls and enjoy a picnic in the picturesque squares. Kids will love the local gelato shops and the nearby horse riding experiences through the beautiful Tuscan countryside, making for unforgettable memories together.

Things to do recommended for groups

Groups visiting Monteriggioni can experience the thrill of the Saltalbero Adventure Park, a zipline and ropes course located 31km away. This outdoor adventure promises excitement and stunning views, making it a perfect activity for those seeking a bit of adrenaline in the heart of Tuscany.

*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 travelling with a group, family, pets, or seeking extended stays, be sure to apply the appropriate filters to meet your needs. 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 features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Monteriggioni with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monteriggioni: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Monteriggioni: If you're in search of holiday rentals offering discounts for stays of a month or more, 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 amenities 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 medieval walled town in Tuscany, offers a captivating blend of history and romance. Explore its ancient walls and quaint streets, where you can savour local Chianti wines and admire the stunning vineyards that surround the area. With a tranquil atmosphere, it's the perfect destination for a relaxing holiday, allowing you to immerse yourself in Tuscan culture while enjoying the breathtaking views of the Chianti hills. Experience the luxury of solitude in this enchanting locale.

  • Siena: Nestled approximately 11km from Monteriggioni, Siena is a captivating city renowned for its rich cultural heritage and stunning medieval architecture. Travellers are drawn to its vibrant piazza, the famous Piazza del Campo, which hosts the iconic Palio horse race. Immerse yourself in the city's artistic treasures at the stunning Siena Cathedral and explore the winding streets filled with charming shops and delightful cafés. The outdoor settings encourage romantic strolls, while its spa offerings provide a relaxing retreat after a day of exploration.
  • Strove: Strove is a picturesque village located in the immediate vicinity of Monteriggioni. This idyllic spot is perfect for those seeking a romantic escape amidst scenic landscapes. Visitors can indulge in rejuvenating spa treatments and enjoy the village's historic charm. Attractions include nearby hot springs and intriguing monuments that reflect the area's storied past. With its tranquil atmosphere, Strove offers a delightful combination of outdoor activities and entertainment, making it a lovely addition to your Tuscan adventure.
  • Abadia a Isola: Abadia a Isola, a quaint village near Monteriggioni, is steeped in history and culture. Known for its serene environment, visitors can explore the impressive monastery and nearby castle that highlight the village's medieval roots. This charming location caters to those looking for a romantic getaway or a unique business retreat infused with cultural experiences. The surrounding countryside is perfect for leisurely walks, and the historical landmarks provide an intriguing glimpse into Tuscany'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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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? It may be beneficial to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to organise by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated area for you to plan new journeys, refine your existing arrangements, or manage your reservations. The properties you’ve saved or booked 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:

  • Terra di Seta (5.3 mi / 8.6 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)
  • Il Molino di Grace Winery (11.6 mi / 18.6 km)
  • Castello di Radda Winery (11.7 mi / 18.8 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:

  • 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)
  • Terme Antica Querciolaia (20.1 mi / 32.4 km)
  • Hedonistic Hiking (4 mi / 6.4 km)
  • Le Caldane Thermal Baths (4.6 mi / 7.3 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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