Some info is shown in its original language. Translate

Vacation rentals in Monteriggioni

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monteriggioni

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

1 of 1 pages1 / 1
Top guest favorite
Apartment in Siena
5.0 out of 5 average rating, 18 reviews

Pool Escape Just Outside Siena

Immerso nel cuore delle colline di Siena a soli 6 km dal centro, il nostro agriturismo è un rifugio di pace e bellezza, dove tradizione autenticità e amore per i cavalli si incontrano. Tra queste dolci colline vengono allevati e allenati i cavalli del Palio, simbolo di passione e tradizione senese. Gli ospiti possono avvicinarsi a questo mondo magico, osservando da vicino l’armonia tra uomo, cavallo e natura e la bellezza di un luogo dove l’eccellenza sportiva incontra il rispetto per l’animale.

Guest favorite
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, 115 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 favorite
Home in Asciano
4.96 out of 5 average rating, 137 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favorite
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

Top guest favorite
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, 293 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.

Guest favorite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Vacation home in Sovicille
4.97 out of 5 average rating, 160 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Top guest favorite
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, 63 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 285 reviews

Casa al Gianni - Capanna

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favorite
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 favorite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 476 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favorite
An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.
Apartment in San Gimignano
4.99 out of 5 average rating, 90 reviews

Herons Superior Apartment - Splendid view!

Goditi una vacanza all'insegna dello stile in questo spazio nel centro di San Gimignano. Finemente arredato e con una vista spettacolare sulle colline toscane, Herons Superior Apartment è pronto a ospitarti insieme alle persone che ami. ___________________________________________________ Tassa di soggiorno da pagare sul posto secondo il seguente calcolo: 2,5€ X numero di ospiti sopra gli 11 anni X numero di notti (si pagano al massimo 5 notti).

Top guest favorite
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, 64 reviews

Cipressini 2 - piscina e vista mozzafiato

Ancient stone farmhouse adjacent to the main farmhouse dating back to the 17. century, located in the heart of the Chianti Classico on the side of a slope with breathtaking views over the Val d'Elsa. Luxuriously renovated and furnished, equipped with every comfort, it is located in such a way as to guarantee absolute privacy.

Popular amenities for Monteriggioni vacation 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.