Holiday Homes in Siena

Free cancellation 2026

Discover the charm of Siena, a picturesque city in Tuscany known for its stunning medieval architecture and vibrant culture. Wander through the historic Piazza del Campo or explore the magnificent Siena Cathedral. Whether you're a history enthusiast or simply looking to relax, Siena offers a delightful escape.

32 handpicked holiday homes

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Panoramic guesthouse in the Siena hills

  • Siena, Italy
  • 2 guests · 1 bedroom
  • Pets are welcome
  • Shared pool

The outdoor pool is only available from April to September

-14%€147 €127/night (6 11 December )

incl. utility costs, cleaning and insurance

Instant Book

Villa with SPA in the heart of Tuscany

  • Arezzo, Italy
  • 6 guests · 3 bedrooms
  • Pets are welcome
  • Private pool

The outdoor pool is only available from May to October

€684/night (7 12 December )

incl. utility costs, cleaning and insurance

Instant BookReduced price

Historic villa with pool in Siena hills

  • Siena, Italy
  • 22 guests · 11 bedrooms
  • Pets are welcome
  • Private pool

The outdoor pool is only available from April to September

-15%€2,115 €1,798/night (6 11 December )

incl. utility costs, cleaning and insurance

Instant BookReduced price

Historic villa overlooking Val d'Orcia

  • Siena, Italy
  • 14 guests · 7 bedrooms
  • Private pool
  • House · 420

The outdoor pool is only available from April to October

-15%€1,368 €1,163/night (14 19 December )

incl. utility costs, cleaning and insurance

Rustic apartment in Siena countryside

  • Siena, Italy
  • 2 guests · 1 bedroom
  • Shared pool
  • Apartment · 40

The outdoor pool is only available from May to August

€211/night (22 27 December )

incl. utility costs, cleaning and insurance

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

Rustic apartment with pool

  • Siena, Italy
  • 4 guests · 2 bedrooms
  • Shared pool
  • Apartment · 80

The outdoor pool is only available from May to August

€302/night (22 27 December )

incl. utility costs, cleaning and insurance

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Discover the Timeless Beauty of Siena with Our Holiday Homes

Nestled in the heart of Tuscany, Siena is a city that enchants visitors with its medieval charm and vibrant culture. Known for its stunning architecture and rich history, this city offers a captivating atmosphere perfect for those seeking a memorable getaway. Whether you're wandering through its narrow streets or exploring the iconic Piazza del Campo, Siena promises an experience filled with wonder.

Unique Holiday Homes in Siena

Our selection of holiday homes in Siena provides the perfect base for your Tuscan adventure. Each home is carefully chosen to offer a unique and personal touch, ensuring you feel right at home from the moment you arrive. From rustic farmhouses surrounded by olive groves to charming apartments within the city walls, there's something for everyone.

Our homes are equipped with all the essentials you need for a comfortable stay, allowing you to relax and immerse yourself in the beauty of the surroundings. Hosts take great pride in creating spaces that reflect the local culture, making your stay truly authentic.

Explore the Rich Culture and Stunning Surroundings

Siena is famous for its cultural attractions and natural beauty. Don't miss the chance to visit the magnificent Siena Cathedral, a masterpiece of Italian Romanesque-Gothic architecture. The annual Palio horse race in Piazza del Campo is a must-see event that captures the spirit of the city.

For those who love the great outdoors, the surrounding Tuscan countryside offers picturesque landscapes perfect for hiking and leisurely strolls. Explore the rolling hills and vineyards that Tuscany is renowned for, and perhaps visit a local winery to sample some of the region's finest wines.

Relax and Unwind in a Peaceful Setting

Escape the hustle and bustle of everyday life with a stay in one of our holiday homes in Siena. The tranquil setting allows you to unwind and enjoy the simple pleasures of life. Picture yourself enjoying a glass of wine on the terrace as the sun sets over the Tuscan hills, or curling up with a good book in a cozy living room.

Whether you're looking for a romantic retreat or a family holiday, Siena offers the perfect backdrop for creating lasting memories. Our holiday homes provide the ideal setting for relaxation and exploration, ensuring your time in Tuscany is unforgettable.

Create Lasting Memories in Siena

A holiday in Siena is more than just a trip—it's a chance to create memories that will last a lifetime. With our carefully curated selection of holiday homes, you'll find the perfect place to stay while you explore all that this enchanting city has to offer.

Book your holiday home in Siena today and embark on a journey filled with history, culture, and breathtaking beauty. Let the charm of Siena captivate you and make your holiday truly special.

Locations – Siena

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.

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.

Words from happy guests

Lovely apartment with everything we needed. Really nice hosts. Beautiful surroundings with attention to detail.

Maibritt from Denmark

Stay for 3 adults

Related 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.

How to Landfolk

Choose a holiday home

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Request your stay

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Pay for your stay

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Feel at home

You’ll receive your host’s Landfolk Guide before arrival to help you get the perfect stay.

Alternative locations

Discover the hidden gems of Friuli – Venezia Giulia, where the Alps meet the Adriatic. Enjoy the vibrant city life in Trieste, explore the historic town of Udine, or savor local wines in the Collio hills. This region offers a perfect blend of nature, culture, and cuisine for an unforgettable holiday experience.

Discover the vibrant culture and stunning landscapes of Sicily, where the Mediterranean sun shines bright. From exploring ancient ruins in Agrigento to savoring fresh seafood in Palermo, Sicily offers a captivating blend of history and culinary delights.

Discover the charm of Apulia, a region where ancient olive groves meet the sparkling Adriatic Sea. Explore the enchanting trulli houses in Alberobello, stroll through the historic streets of Lecce, and enjoy the vibrant coastal life in Gallipoli.

Discover the charm of Campania, where history and natural beauty unite. From the ancient ruins of Pompeii to the stunning Amalfi Coast, there's something for everyone to enjoy. Savor the region's delicious cuisine and explore vibrant cities like Naples for an unforgettable getaway.

Discover the hidden gem of Italy's Adriatic coast. Marche offers charming hilltop towns, stunning beaches, and a rich tapestry of culture and history. Perfect for a relaxing escape or a cultural adventure with family and friends.

Discover the charming region of Liguria, where picturesque coastal villages meet the azure waters of the Italian Riviera. Enjoy hiking through the famous Cinque Terre trails or savoring fresh seafood in the quaint harbors of Portofino and La Spezia.

Nestled between the Apennine Mountains and the Adriatic Sea, Abruzzo offers diverse experiences for nature enthusiasts and culture lovers alike. From exploring ancient hilltop villages to hiking in national parks, there's something for everyone to enjoy.

Discover the enchanting island of Sardinia, where crystal-clear waters meet stunning landscapes. Whether you're exploring ancient ruins or relaxing on sandy beaches, Sardinia offers a blend of history and natural beauty perfect for your next getaway.

Discover the enchanting region of Lazio, where ancient history meets stunning landscapes. From the bustling streets of Rome to the serene shores of Lake Bracciano, Lazio offers a delightful mix of culture and nature for every traveler.

Nestled in the heart of Italy, Piedmont offers a blend of rich history, exquisite wines, and culinary delights. Explore its rolling vineyards, charming villages, and the majestic Alps for a truly unforgettable experience.

Nestled in the heart of Italy, Umbria offers a charming escape with its rolling hills, historic towns, and delectable cuisine. Discover hidden gems like Assisi and Orvieto, or enjoy the natural beauty of Lake Trasimeno. Perfect for a tranquil getaway filled with culture and relaxation.

Discover the captivating charm of Aosta Valley, where majestic peaks meet quaint villages. Enjoy scenic hikes, explore ancient castles, and indulge in delicious local cuisine. Whether you're hitting the slopes or soaking up the culture, every moment here promises a unique adventure.

Nestled in the heart of the Alps, Trentino – Alto Adige/Südtirol offers a perfect blend of Italian and Austrian cultures. Explore the majestic Dolomites, enjoy outdoor adventures, or relax in charming towns like Bolzano and Trento. A destination for all seasons, it's ideal for family escapes or romantic getaways.

Discover the enchanting region of Lombardy, where the majestic Alps meet serene lakes and lively cities. Explore Milan's fashion scene, the stunning Lake Como, and charming villages nestled in picturesque landscapes. A perfect destination for families, couples, and friends seeking diverse experiences.

Discover the charm of Calabria, where the sun-kissed beaches meet historic towns and lush mountains. Enjoy a rich tapestry of culture, cuisine, and natural beauty perfect for families and friends seeking relaxation and adventure.

Discover Emilia-Romagna, a region where culinary delights and historic charm come together. From the vibrant city of Bologna to the serene landscapes of the Apennines, there's plenty to explore. Wander through medieval towns or savor local delicacies like Parmigiano Reggiano and balsamic vinegar.

Discover the charm of Veneto, a region steeped in history and culture. Wander through the romantic streets of Venice, explore the art-filled cities like Verona and Padua, or savor the exquisite wines of the Valpolicella region. Whether you're seeking adventure or relaxation, Veneto offers a tapestry of experiences for every traveler.

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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