Monteriggioni holiday lettings

We found 2,799 holiday rentals — enter your dates for availability

Discover a selection of 28 homes, 61 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:26 Dec - 2 Jan

Image gallery for "Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

Pool
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

Siena, Tuscany

5% off
Price is £3,683
for 7 nights, 1 villa
£526 per night
includes taxes & fees
"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

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Find out more about Monteriggioni

Find out more about Monteriggioni

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:

  • Castello di Monsanto (8.9 mi / 14.3 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)
  • 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)
  • Alta Val d'Elsa River Park (4.5 mi / 7.3 km)
  • Le Caldane Thermal Baths (4.6 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, the most appealing area to stay in is the historic centre of the village. This charming walled town exudes a medieval atmosphere, making it an enchanting base for exploring the surrounding Tuscan landscape. Within the walls, you'll find a delightful assortment of properties, many of which offer stunning views of the countryside. The area is particularly popular among visitors, with a variety of accommodations available, ranging from quaint apartments to rustic villas.

Staying in the historic centre allows easy access to top attractions such as the impressive Monteriggioni Castle, which dates back to the 13th century, and the beautiful Church of Santa Maria Assunta. Exploring the narrow cobblestone streets, you'll discover quaint shops and local eateries serving traditional Tuscan cuisine, enhancing your experience of this picturesque setting.

Another lovely area to consider is the surrounding countryside, where you'll find several holiday rentals located among vineyards and olive groves. This option provides a more tranquil atmosphere while still being just a short drive away from the village itself. Here, you can enjoy the stunning landscape and partake in wine tasting tours at nearby wineries, making it an ideal choice for those looking to immerse themselves in the region's rich culture.
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.
What is the most popular type of holiday rental accomodation in Monteriggioni?
In Monteriggioni, apartments are the most popular type of holiday rental, with approximately 54 available in picturesque locations near the medieval walls and the charming town square. These apartments typically feature fully equipped kitchens, comfortable living areas, and often offer stunning views of the surrounding Tuscan countryside.
Are there any family house rentals in Monteriggioni?
In Monteriggioni, Tuscany, there are numerous family-friendly house rentals available, with approximately 65 options to choose from. This enchanting medieval village offers a picturesque setting for families looking to explore the beauty of the Tuscan countryside. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor terraces ideal for enjoying the stunning views.

Visitors will find themselves within easy reach of local attractions, such as the iconic walls of Monteriggioni itself and the nearby vineyards that define the region. Additionally, properties often include amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all family members.
Can I rent a holiday home with a pool or hot tub in Monteriggioni?
In Monteriggioni, there are ample holiday homes available for rent that feature pools and hot tubs, with about 72 options to choose from. This picturesque medieval village, set in the scenic Tuscan countryside, offers a variety of properties ranging from charming villas to rustic farmhouses. Many of these rentals come equipped with private pools, ideal for enjoying the warm Tuscan sun, and some may even feature luxurious hot tubs for ultimate relaxation.
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, offering a delightful experience for travellers with pets. This picturesque medieval town is surrounded by stunning Tuscan landscapes, making it an ideal spot for those looking to enjoy both comfort and natural beauty. Many holiday rentals in the area come equipped with amenities such as private gardens, outdoor dining areas, and fully equipped kitchens, providing a cozy feel for guests and their furry companions.
Are there any remote work holiday rentals in Monteriggioni?
In Monteriggioni, Tuscany, there are numerous remote work holiday rentals available, with around 92 options to choose from. This picturesque medieval town, surrounded by ancient walls and rolling hills, provides a serene setting for those looking to combine work and leisure. Many of the properties are equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, and comfortable office chairs. Some rentals even offer additional features such as laptop-compatible safes and computer monitors, ensuring that you can stay productive during your stay. 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 feature a variety of desirable amenities that enhance the guest experience. Most properties come equipped with a kitchen, allowing travellers to prepare their own meals and enjoy the local cuisine at their convenience. Additionally, many rentals include a private pool, which provides a refreshing escape during the warm Tuscan days. Guests can also expect complimentary Wi-Fi in their rooms, ensuring they stay connected throughout their stay. Other common amenities include refrigerators and microwaves, making it easier to store and heat up food.
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 wane and the weather remains pleasantly warm. This month marks the peak of the grape harvest in Tuscany, offering a fantastic opportunity for wine enthusiasts to explore local vineyards and participate in tastings. The charming medieval village, with its stunning walls and picturesque surroundings, provides a great backdrop for leisurely strolls and outdoor dining.

During this period, temperatures typically range from the mid-teens to low 20s Celsius, creating a comfortable environment for sightseeing and enjoying the beautiful Tuscan countryside. Visitors can appreciate the blend of culture and nature, whether wandering through quaint streets or taking in stunning views of the rolling hills.

If you're looking for a more budget-friendly option, consider visiting Monteriggioni in February. Although it's the low season, this month offers a unique chance to experience the region's tranquillity, alongside the opportunity to enjoy local cuisine in a more intimate setting. The cooler temperatures (around 5-10 degrees Celsius) invite cosy moments by the fire in local trattorias, allowing you to savour authentic Tuscan dishes without the bustling crowds.
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 take part in the enchanting medieval atmosphere of this small hilltop village. The well-preserved walls and towers of the fortress provide a stunning backdrop for exploration, and walking along the ancient ramparts offers breathtaking views of the surrounding Tuscan countryside.

The central square, Piazza Roma, is a charming spot where travellers can find local shops and cafes, superb for sampling traditional Tuscan cuisine. Just outside the village, the beautiful Chianti region beckons with its picturesque vineyards and olive groves, offering opportunities for wine tasting and leisurely strolls.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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