Holiday Homes in Monteriggioni

Free cancellation 2026

Step back in time in the enchanting medieval town of Monteriggioni. Walk along the ancient walls, explore charming cobblestone streets, and enjoy the stunning views of the Tuscan countryside. Perfect for a relaxing getaway, this gem offers a truly unique Italian experience.

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Historic villa with pool in the heart of Chianti

  • Siena, Italy
  • 10 guests · 5 bedrooms
  • Pets are welcome
  • Private pool

The outdoor pool is only available from May to October

€784/night (6 11 December )

incl. utility costs, cleaning and insurance

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Discover the Timeless Charm of Monteriggioni

Nestled in the heart of Tuscany, Monteriggioni offers a unique blend of medieval architecture, stunning landscapes, and rich cultural experiences. This small walled town, with its well-preserved towers and cobblestone streets, invites you to step back in time and explore its historical wonders.

Whether you're wandering through the ancient streets or enjoying panoramic views of the surrounding countryside, Monteriggioni provides a perfect backdrop for a relaxing holiday. The town's charm lies not only in its historic allure but also in the tranquil atmosphere that surrounds it.

Holiday Homes That Capture the Essence of Tuscany

Our selection of holiday homes in Monteriggioni offers you the chance to experience the authentic Tuscan lifestyle. Each home is carefully chosen for its character and comfort, providing a cozy retreat after a day of exploration.

From rustic farmhouses with terracotta floors and wooden beams to elegant villas with private gardens, our holiday homes cater to every taste. Enjoy modern amenities while basking in the timeless beauty of traditional Tuscan architecture.

Immerse Yourself in Local Culture and Activities

Monteriggioni is not just about its historical significance; it also offers a range of activities for those seeking adventure or relaxation. Take a leisurely walk along the ancient city walls, or visit the Monteriggioni in Arme Museum to learn more about the town's medieval past.

For nature enthusiasts, the surrounding vineyards and olive groves provide excellent opportunities for hiking and cycling. Wine tastings at local vineyards offer a chance to savour the rich flavours of Tuscany, and nearby towns like Siena and San Gimignano are perfect for day trips.

A Haven for Relaxation and Rejuvenation

Escape the hustle and bustle of daily life and unwind in the serene setting of Monteriggioni. The peaceful countryside and charming holiday homes create an ideal environment for relaxation. Imagine spending your afternoons enjoying a glass of wine on the terrace while taking in the breathtaking views of rolling hills.

Whether you're looking to relax or explore, Monteriggioni offers the perfect blend of tranquility and adventure. Let the magic of Tuscany envelop you as you create unforgettable memories in this enchanting location.

Related locations

Nestled in the rolling hills of Tuscany, Chiusdino is a charming village with medieval roots. Discover the captivating ruins of San Galgano Abbey and the legendary Sword in the Stone for a touch of history and mystery.

Nestled in the rolling hills of Tuscany, Monticiano offers a serene escape with its charming streets and rustic charm. Explore the nearby Petriolo hot springs or enjoy a peaceful walk through the enchanting woods. A perfect spot for a relaxing getaway.

Nestled in the heart of Tuscany, Casole d'Elsa invites you to explore its charming medieval streets and breathtaking landscapes. Enjoy local wines, delicious Italian cuisine, and the serenity of the Tuscan hills.

Escape to Montalcino, a charming town nestled in Tuscany's rolling hills. Known for its rich history and the famous Brunello di Montalcino wine, it's a perfect spot for exploring vineyards and savoring Italian cuisine. Wander through medieval streets and take in stunning views of the idyllic countryside.

Nestled in the heart of Tuscany, Montepulciano offers a charming blend of Renaissance architecture and rolling vineyards. Wander through its medieval streets, savor the local cuisine, or enjoy a glass of the renowned Vino Nobile di Montepulciano as you take in the stunning views of the surrounding countryside.

Discover the charm of Sovicille, a picturesque village nestled in the heart of Tuscany. Wander through its quaint streets, enjoy the surrounding countryside, and savor the local cuisine that makes this area so special.

Nestled in the scenic hills of Tuscany, Cetona offers a charming escape with its medieval charm and stunning landscapes. Explore the quaint village streets, visit the nearby Mount Cetona for breathtaking views, and indulge in local Tuscan cuisine.

Step back in time and wander through the medieval streets of San Gimignano, famous for its stunning skyline of ancient towers. Enjoy local delights like Vernaccia wine and explore the charming boutiques and art galleries that line the cobblestone paths.

Nestled in the heart of Tuscany, Buonconvento invites you to stroll through its charming streets and discover its rich history. Enjoy the delightful local cuisine and explore nearby vineyards for an authentic Italian experience.

Nestled in the heart of Tuscany, Castelnuovo Berardenga offers a charming escape with its rolling hills and picturesque vineyards. Discover the rich history and savor the local wines while enjoying the tranquil Italian countryside.

Discover the charming village of Trequanda, nestled in the rolling hills of Tuscany. Wander through its quaint streets, soak up the local culture, and enjoy delightful Italian cuisine. A perfect getaway for those seeking tranquility and picturesque landscapes.

Nestled in the heart of Tuscany, Sinalunga offers a perfect blend of rolling hills and charming Italian culture. Explore the picturesque countryside, savor local wines, and immerse yourself in the rich history of this delightful town.

Nestled in the heart of Tuscany, Asciano offers a charming escape with its medieval streets and rolling hills. Discover the beauty of the Crete Senesi, visit the ancient Abbey of Monte Oliveto Maggiore, or simply relax and enjoy the local cuisine and wines.

Nestled in the heart of Tuscany, Gaiole in Chianti offers a charming blend of rustic beauty and cultural richness. Wander through vineyards, savor exquisite wines, or explore the historic Castello di Brolio for a truly memorable experience.

Nestled in the heart of Tuscany, Radda in Chianti offers a picturesque escape with its rolling vineyards and charming medieval streets. Discover the local wineries and enjoy a taste of authentic Italian cuisine in a serene setting.

How to Landfolk

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Alternative locations

Dive into the coastal charm of Livorno, where vibrant markets, beautiful canals, and the famous Terrazza Mascagni await. Perfect for families and friends, this Tuscan gem offers a unique blend of history, culture, and seaside relaxation.

Explore the enchanting region of Massa-Carrara, where the rugged beauty of the Apuan Alps meets the serene coastline. Discover charming villages, indulge in local cuisine, and visit the famous marble quarries that have shaped the area's history.

Discover Florence, a city steeped in art, history, and culture. Wander through its charming streets, marvel at the stunning architecture of the Duomo, and indulge in authentic Italian cuisine at local trattorias. Perfect for families, couples, and friends looking for a memorable getaway.

Explore the charming city of Pisa, famous for its Leaning Tower and delightful Italian culture. Wander through its historic streets, enjoy authentic cuisine, and discover hidden gems in this enchanting Tuscan destination.

Discover the charm of Prato, a delightful city in Tuscany known for its rich textile history and stunning Renaissance architecture. Wander through the historic center, savor local cuisine, and enjoy the vibrant arts scene.

Discover the charm of Arezzo, a historic town in Tuscany known for its picturesque landscapes and rich cultural heritage. Stroll through its medieval streets, visit the impressive Cathedral of San Donato, or enjoy a leisurely afternoon in one of its beautiful piazzas.

Nestled in the heart of Tuscany, Pistoia offers a charming blend of medieval architecture and vibrant local culture. Wander through its lively markets, explore the historic city center, or take a day trip to the nearby hills for breathtaking views.

Discover the charming city of Lucca, nestled in the heart of Tuscany. With its well-preserved Renaissance walls, quaint cobblestone streets, and vibrant piazzas, Lucca is perfect for leisurely strolls and soaking in Italian culture. Don't miss the chance to cycle around the ancient city walls or indulge in delicious local cuisine.

Discover Grosseto, a charming city in the heart of Tuscany. Enjoy strolls through its historic center, explore the nearby Maremma Natural Park, or relax on the pristine beaches of the Tyrrhenian coast. Perfect for a memorable getaway with family or friends.

3 reasons to choose a Landfolk holiday home

Cleaning included

Don’t worry about the cleaning – we’ll take care of it for you!

No surprises

At Landfolk you’ll only get one price, and that’s the price we show. .

Pay how you like

Whether you prefer to pay with card or bank transfer, all at once or split, !

Why rent out through Landfolk?

You will be in the best company with other handpicked holiday homes and you can share it flexibly and on fair terms.

No lock-in period

You decide when, to whom and how often you rent out.

Personal connection

Your guests treasure the holiday home life as much as you.

Fair fees and terms

Only 5% of your earnings go to Landfolk.

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