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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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Top Guest favourite
A bright living area features a light wooden dining table surrounded by four white chairs. A dark blue sofa is positioned against the wall, and two windows allow natural light to enhance the space. The view outside includes hints of greenery.
Apartment in San Gimignano
4.99 out of 5 average rating, 195 reviews

Il Sogno Toscano-moderno in centro a San Gimignano

Il Sogno Toscano, appartamento esclusivo nel centro storico di San Gimignano! Questo appartamento di 100 m²,situato a pochi passi dalle celebri torri medievali, è la base ideale per esplorare il borgo patrimonio UNESCO. L’appartamento dispone di ampi spazi luminosi, una cucina completamente attrezzata, soggiorno con vista panoramica sui colli toscani, due camere da letto eleganti e due bagni spaziosi. Godetevi una vista spettacolare e rilassatevi al tramonto con un buon bicchiere di vino locale.

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Top 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
4.91 out of 5 average rating, 117 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

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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)

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Top Guest favourite
Home in Monteriggioni
4.98 out of 5 average rating, 40 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

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Top 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, 296 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.

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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
4.97 out of 5 average rating, 198 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!

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Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 107 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

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Top Guest favourite
Condo in Colle di Val d'Elsa
5.0 out of 5 average rating, 29 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.

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Top Guest favourite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena
4.97 out of 5 average rating, 115 reviews

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

ValueFamilyLong stay

Top Guest favourite
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Apartment in Quercegrossa
4.98 out of 5 average rating, 87 reviews

Tuscany jem: La Casa del Fattore del Chianti

Questo meraviglioso appartamento appena ristrutturato conserva il fascino dei casolari del Chianti e le comodità di un appartamento moderno. La casa è situata all'interno del complesso della Fattoria di Petroio, azienda vitivinicola del Chianti Classico. Potrete godere della bellezza e della tranquillità delle colline del Chianti, mentre vi immergete nella vita dinamica di un'azienda dedita alla produzione di vini di qualità.

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Guest favourite
An aerial view captures the expansive countryside, dotted with vineyards and olive groves. The large swimming pool is framed by lush greenery, while the villa's garden offers a serene atmosphere. Gentle hills roll in the background under a clear, blue sky.
Villa in Poggibonsi
4.95 out of 5 average rating, 73 reviews

Villa with pool in Chianti Area

Amazing Entire Tuscan apartment in an indipendet part of our family Villa in the Chianti! Panoramic 360° view, independent entrance, parking, private garden with BBQ, big SWIMMING POOL, 4 Bedrooms, large living area with big tuscan fireplace, equipped kitchen and laundry. High speed WIFI. Between Siena and Florence in a strategic position close to the main Chianti roads and many characteristic villages!!

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Top Guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni
4.93 out of 5 average rating, 455 reviews

Comfort Apartment tra i vigneti del Chianti

Appartamento al piano superiore della struttura caratterizzato da una vista meravigliosa sulle colline del Chianti, uliveti o sul patio. Ristrutturato mantenendo il fascino delle loro antiche mura ma aggiungendo ogni comfort. Comprende soggiorno, angolo cottura, una camera da letto matrimoniale, un bagno privato con doccia, aria condizionata.

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Popular amenities for Monteriggioni holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Monteriggioni

Top Guest favourite
An infinity pool reflects the sky, surrounded by lush greenery and cypress trees. The pool's edge seamlessly blends into the landscape, overlooking rolling hills and olive groves. Sun loungers are positioned nearby, providing a serene outdoor setting.
Barn in Castellina in Chianti
5.0 out of 5 average rating, 67 reviews

Cipressini 2 - piscina e vista mozzafiato

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Top Guest favourite
Condo in Siena
5.0 out of 5 average rating, 21 reviews

Luxury Penthouse overlooking Piazza del Campo

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Guest favourite
Apartment in Siena
5.0 out of 5 average rating, 20 reviews

Pool Escape Just Outside Siena

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Top Guest favourite
The charming barn features a rustic stone exterior, framed by lush greenery. A spacious patio can be seen, adorned with vibrant flowers and equipped with outdoor seating and a shaded area. The structure is surrounded by well-maintained lawn and trees, enhancing the tranquil atmosphere.
Barn in Monteriggioni
4.98 out of 5 average rating, 64 reviews

Charming Barn with Pool - Chianti Area

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Guest favourite
A distant view of Monteriggioni is showcased against a colorful sunset, with the silhouette of its ancient walls contrasting the warm hues of the evening sky. Olive trees are visible in the foreground, enhancing the scenic landscape.
Apartment in Monteriggioni
4.87 out of 5 average rating, 38 reviews

Il Mandorlo di Monteriggioni

LocationOutdoor spacesBreakfast

Top Guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5.0 out of 5 average rating, 69 reviews

AnticaVista, Luxury Apartment with Tower Views

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Top Guest favourite
Home in Siena
4.96 out of 5 average rating, 26 reviews

Private House for 4P- La Capanna Di Azzurra

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An aerial view of the Casale reveals a charming stone structure surrounded by lush greenery. A private circular pool is set in the garden, accompanied by sun loungers arranged around it. Mature trees contribute to the serene atmosphere of the property.
Villa in Monteriggioni
4.83 out of 5 average rating, 105 reviews

Farmhouse in an old watermill in the Chianti hills

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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.

Destinations to explore