Monteriggioni vacation rentals

We found 2,828 vacation rentals — enter your dates for availability

Discover a selection of 27 homes, 63 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:Nov 14 - Nov 21

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

Pool
10 out of 10 rating
Exceptional
(11 reviews)

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

Siena, Tuscany

6% off
Price is CA $731
CA $5,739 total
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 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:

  • 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)

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 considering a vacation rental in Monteriggioni, the best area to stay is within the medieval walls of the town itself. This historic centre offers a truly immersive experience, with charming stone buildings and picturesque streets that transport you back in time. Staying here provides immediate access to top attractions such as the impressive fortress walls, which you can walk along for stunning views of the surrounding Tuscan countryside. The nearby Church of Santa Maria Assunta is another highlight, showcasing beautiful Romanesque architecture.

For those who prefer a slightly quieter setting while still being close to the action, the surrounding countryside is also appealing. There are several vacation properties available that offer a serene atmosphere, with easy access to nature trails and vineyards. This area allows guests to enjoy the tranquillity of rural Tuscany while remaining just a short drive from Monteriggioni's vibrant centre.
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 travelling 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.
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, travellers should consider nearby coastal areas such as Castiglione della Pescaia or the stunning beaches of the Maremma region. Although Monteriggioni itself is not directly on the coast, it is within a reasonable drive to these beautiful seaside locations.

In Castiglione della Pescaia, visitors can find charming beach houses that come with amenities such as private terraces, outdoor dining areas, and easy access to sandy beaches. Many of these properties are equipped with modern kitchens, allowing for self-catering, and some even offer direct beach access or views of the Mediterranean Sea. The vibrant local area features a variety of restaurants and shops, enhancing the vacation experience.
What is the most popular type of vacation rental accomodation in Monteriggioni?
In Monteriggioni, apartments are the most popular type of vacation rental, with around 54 available throughout this picturesque medieval village. Many of these apartments are situated in charming buildings that reflect the region's historical architecture, often featuring fully equipped kitchens, comfortable living areas, and balconies or terraces with scenic 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—approximately 65 in total. This charming medieval village offers a picturesque backdrop for families seeking a memorable vacation. Many of these properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.
Can I rent a vacation home with a pool or hot tub in Monteriggioni?
In Monteriggioni, there are plenty of vacation homes available for rent that feature pools or hot tubs, with around 72 options to choose from. This picturesque medieval town in Tuscany is surrounded by stunning landscapes, making it an ideal location for relaxation and exploration. Many of these properties offer private pools and hot tubs, along with amenities such as spacious terraces, fully equipped kitchens, and outdoor dining areas, great for enjoying the beautiful Tuscan weather.
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. 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 range of amenities to enhance your stay. Many properties feature spacious gardens, allowing pets to roam freely, as well as well-equipped kitchens for preparing meals after a day of exploring the beautiful Tuscan countryside.
Are there any remote work vacation rentals in Monteriggioni?
In Monteriggioni, there are numerous remote work-friendly vacation rentals available, with around 92 options to choose from. This charming medieval town in Tuscany offers a picturesque setting for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, and comfortable desk chairs. Some accommodations even feature additional perks such as laptop-compatible safes, computer monitors, and private office spaces, ensuring a productive environment. 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 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, vacation 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 vacation rental?
September is the most popular time to visit Monteriggioni, as travellers flock to this picturesque Tuscan village to experience the beautiful weather and vibrant local culture. During this period, the landscape is rich with the golden hues of late summer, superb for exploring the medieval architecture and surrounding vineyards. The peak season runs from August to October, making it an ideal time for those seeking to immerse themselves in outdoor activities, local festivals, and scenic walks through the stunning countryside.

In September, temperatures typically hover in the mid-teens to low 20s Celsius, providing a comfortable climate for sightseeing and outdoor dining. The harvest season also adds a unique charm to the experience, allowing visitors to indulge in local cuisine and sample exquisite wines. The village's enchanting atmosphere is enhanced by events like the medieval festival, where you can witness historical reenactments and savour traditional dishes.

For those looking to save on travel costs, February offers a quieter experience and is generally more affordable for vacation rentals. It's cooler, with temperatures ranging from 5 to 10 degrees Celsius, this time allows for a peaceful exploration of Monteriggioni's historic sites without the crowds. It's a fantastic opportunity for a more intimate experience of the village's charm.
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 enjoy the enchanting medieval atmosphere of this well-preserved fortress town. The iconic walls of Monteriggioni are one of its main attractions, offering stunning panoramas of the surrounding Tuscan countryside. Within the walls, you can explore charming narrow streets that lead to quaint shops and local eateries serving traditional Tuscan cuisine.

The Church of Santa Maria, located in the main square, is another highlight, showcasing beautiful artwork and a serene ambience. The nearby Monteriggioni Castle provides an opportunity for history enthusiasts to delve into the town's past.
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 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 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.

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