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Holiday houses in Monteriggioni

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Top-rated holiday rentals in Monteriggioni

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 337 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Guest favourite
The stone farmhouse, characterized by a rustic façade, features arched doorways and shuttered windows. Lush greenery surrounds the entrance, offering a serene landscape. A gravel driveway leads to the main entrance, highlighting the spaciousness of the property.
Farm stay in Monteriggioni
4.9 out of 5 average rating, 114 reviews

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

Guest favourite
Villa in Monteriggioni
4.97 out of 5 average rating, 174 reviews

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

Top Guest favourite
Home in Monteriggioni
4.97 out of 5 average rating, 39 reviews

Toscana-Monteriggioni- Chianti- Francigena-

L’appartamento è una porzione di casale tipico toscano, anticamente Mulino (la parte più antica risale al 1200 circa) è immerso nella natura e in posizione strategica sulla via Francigena, a 2 km da Monteriggioni, 10 km da Siena e vicino a San Gimignano, Volterra e Firenze. L'appartamento è composto da cucina a vista attrezzata, bagno con doccia, camera con letto matrimoniale e camera con due letti singoli. La zona giorno, dispone di comodo divano letto con tv, wi-fi e aria condizionata

Guest favourite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.95 out of 5 average rating, 291 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 189 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

Top Guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.99 out of 5 average rating, 135 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Guest favourite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Top Guest favourite
Condo in Colle di Val d'Elsa
5.0 out of 5 average rating, 25 reviews

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

Guest favourite
Dome in Volterra
4.95 out of 5 average rating, 155 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Top Guest favourite
Apartment in Barberino Val d'Elsa
5.0 out of 5 average rating, 21 reviews

Lorenzo Charme nel Chianti

Questo spazio unico ha uno stile tutto suo. Curato nel minimi dettagli, ha tutte le caratteristiche per favorire una vacanza nello Charme e nel lusso. Adatto a tutti e dotato di ogni confort. Si trova in una posizione centrale adatto a visitare tutti i luoghi di maggior interesse; Firenze si trova a soli 30 Km e Siena a 35 Km.

Guest favourite
A spacious bedroom features a four-poster bed draped with sheer white curtains. Exposed wooden beams adorn the ceiling, while the stone walls add rustic charm. A window with elegant lace curtains offers natural light and a view of the picturesque surroundings.
Condo in Monteriggioni
4.98 out of 5 average rating, 43 reviews

LUNA Romantic bedroom in Monteriggioni

A romantic room in the heart of Monteriggioni, a XII century medieval village on the Francigena way, an ancient walking trail that takes pilgrims from Canterbury to Rome. The room overlooks the main square of the village and offers our guests the unique experience of standing in one of the most beautiful villages in Tuscany!

Popular amenities for Monteriggioni holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Monteriggioni?

    Monteriggioni has stays within its fortified village, country villas surrounded by olive groves, and rustic farmhouses in the countryside. Each setting allows guests to experience the town’s historic atmosphere and scenic vistas.

  • What are the best things to do in Monteriggioni with kids?

    Families often explore Monteriggioni’s castle walls, try hands-on workshops themed around medieval history, and enjoy village festivals with interactive activities. Open green spaces and guided walks let kids experience the countryside’s nature and stories.

  • What are some of the best things to do in Monteriggioni?

    Stroll the medieval walls of Monteriggioni, discover the historic Porta Franca gate, and explore the main piazza’s small museums. Local wineries and olive groves around Monteriggioni invite tastings and guided visits.

  • How is the weather in Monteriggioni?

    Monteriggioni has mild winters, with temperatures around 36–55°F (2–13°C), and warm, dry summers near 65–90°F (18–32°C). Spring and autumn often bring moderate rainfall and comfortable temperatures, making them appealing seasons for exploring.

  • When is the best time to visit Monteriggioni?

    Late spring and early autumn are often suggested for visiting Monteriggioni, with comfortable temperatures and fewer crowds. This period also brings local festivals, blooming landscapes, and harvest traditions.

  • What are the best places to visit in Monteriggioni?

    Explore Monteriggioni’s medieval walls, the Church of Santa Maria Assunta, and the Armory Museum. The main piazza is a welcoming spot to experience local life and events.

  • What are some hiking trails in Monteriggioni?

    Monteriggioni has scenic trails along sections of the historic Via Francigena and gentle routes through Chianti hills and forests. Walking the footpaths around the village, you may pass vineyards, olive groves, and wildflower meadows.

  • What are some family activities we can do in Monteriggioni?

    Families enjoy climbing Monteriggioni’s medieval walls, visiting small museums with interactive displays, and joining local food or craft workshops. Open squares provide space for children to play and experience the village’s traditions.

  • What are some of the best day trip ideas from Monteriggioni?

    Many travelers explore nearby hill towns with Etruscan sites, vineyards, and Renaissance art. Popular day trips include visits to historic Siena, local markets, or countryside village festivals.

  • Are there any pet friendly accommodations available in Monteriggioni?

    Monteriggioni has a selection of pet-friendly stays, including apartments, country homes, and traditional villas. Many hosts are happy to welcome travelers with pets, especially in the scenic countryside and village surroundings.

  • What are some local tips for visiting Monteriggioni?

    Start your day early to enjoy Monteriggioni’s quieter atmosphere and bring cash for small artisan shops. Sampling local olive oil and joining a guided village walk are often recommended for a more immersive experience.

  • What is Monteriggioni known for?

    Monteriggioni is known for its striking circular medieval walls, historic towers, and preserved village center. The area has a rich legacy along the Via Francigena pilgrimage route and is often highlighted for its role in regional poetry and history.

  • What are the best hidden gems to explore in Monteriggioni?

    Explore Monteriggioni’s quieter medieval alleys, lesser-known artisan workshops, and the ancient Oliveta Abbey nestled around the area. The countryside also has peaceful trails lined with wildflowers and cypress trees.

  • What are the best foods to try in Monteriggioni?

    In Monteriggioni, savor local specialties such as wild boar stew, handmade pici pasta, and pecorino cheese. Many enjoy sharing bruschetta topped with local olive oil, along with traditional Tuscan desserts like cantucci dipped in sweet wine.

  • What should I bring for a trip to Monteriggioni?

    Pack comfortable walking shoes, a sun hat, and layers for changing temperatures, especially in spring or autumn. A small reusable water bottle is practical for wandering medieval streets and exploring the countryside.

  • What is the nightlife in Monteriggioni like?

    Monteriggioni’s nightlife centers on relaxed cafés, wine bars, and live music in the main piazza or historic venues. Warm evenings bring quieter gatherings and seasonal events featuring music and local food.

  • What are the most popular events or festivals in Monteriggioni?

    Monteriggioni’s medieval festival in summer is often highlighted, with reenactments, themed markets, and historical performances. Throughout the year, the village hosts food celebrations, artisan fairs, and music events rooted in local tradition.

  • Are there family friendly vacation rentals in Monteriggioni?

    Monteriggioni has a range of family-friendly vacation rentals, including spacious homes and village apartments with kitchen facilities. Many properties feature easy access to outdoor spaces for children and shared family activities.