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Holiday rentals in Radicondoli

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Top-rated holiday rentals in Radicondoli

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

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Guest favourite
Home
4.96 out of 5 average rating, 132 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 favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 151 reviews

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay
4.99 out of 5 average rating, 498 reviews

Agriturismo Fattoria La Parita

Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

Top guest favourite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home
5 out of 5 average rating, 107 reviews

Casa del Capitano | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment
5 out of 5 average rating, 335 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

Guest favourite
An aerial view captures the scenic landscape surrounding an ancient farm complex nestled within lush greenery. A swimming pool is visible at the center, surrounded by sun loungers, while rolling hills stretch into the distance under a soft evening light.
Holiday home
4.94 out of 5 average rating, 125 reviews

Podere La Castellina - N°2 LECCETO

Appartamento in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. L'appartamento situato al piano terra può ospitare comodamente 2 persone e comprende: - soggiorno con tv - cucina con forno e piastre elettriche - camera matrimoniale - bagno con ampia doccia - tavolo esterno privato A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment
5 out of 5 average rating, 148 reviews

Mascagni Farmhouse in Val d'Orcia Pienza

Risali le iconiche colline toscane fino a Mascagni Organic Farm, un'azienda biologica dove ti aspetta la tua nuova casa: un fienile del 1500 finemente ristrutturato immerso tra olivi e campi di grano. Rilassati prendendo una tazza di tè, raccogli rosmarini e lavande nel giardino con vista mozzafiato sulla Val d'Orcia. Riscopri la tua vera natura tra i campi incontaminati e gli olivi: qui le passeggiate e i giri in bici non hanno confini! Pronto a creare ricordi che dureranno tutta la vita?

Top guest favourite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower
5 out of 5 average rating, 111 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 218 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
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
4.92 out of 5 average rating, 269 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 favourite
Flat
5 out of 5 average rating, 11 reviews

Monolocale Antico Fienile

Open Space Antico Fienile in Radicondoli is a welcoming open-plan apartment nestled in the peaceful Tuscan hills, perfect for a relaxing, nature-filled holiday. The accommodation features a bright living area with a fully equipped kitchen, lounge with sofa and TV, sleeping area with a double bed, and a charming mezzanine with a second double bed. There is also a bathroom with a shower cabin. The apartment accommodates up to 2 adults and 2 children.

Top guest favourite
The open living space features a spacious gray sectional sofa with accent lighting reflecting off the textured brick arch ceiling. A flat-screen TV is mounted on the wall, and a decorative sculpture rests on a stylish table, enhancing the modern design.
Loft
4.97 out of 5 average rating, 124 reviews

Il Frantoio - Charming Loft in the old town

This elegant and spacious Loft “Il Frantoio”, with a living area of 160 m², is located in the old town of the medieval village Radicondoli. The open space kitchen and livingroom area is designed to give a high comfort and reminds us the ancient function of this bluilding that was the oil mill of the comunity. The Loft was recently completly restored with a high focus on comfort and best quality materials.

Popular amenities for Radicondoli holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Radicondoli?

    Stays in Radicondoli often include restored farmhouses, stone cottages, or apartments in the village center. Many visitors enjoy accommodations surrounded by hills, olive groves, and rural scenery.

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

    Families often explore Radicondoli’s pedestrian-friendly streets, picnic in nearby forests, or join craft workshops and village fairs in summer. Open green spaces make it easy for children to play and discover nature.

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

    Explore Radicondoli’s medieval streets, visit local artisan workshops, or join seasonal festivals celebrating arts and food. Walking in the countryside around the village is often recommended for nature lovers.

  • How is the weather in Radicondoli?

    Radicondoli has cool winters around 37–55°F (3–13°C), while summers are warm with afternoons reaching 89°F (31°C). Spring and fall bring milder weather and varied rainfall, inviting outdoor exploration.

  • When is the best time to visit Radicondoli?

    Late spring through early fall is often recommended for mild weather, outdoor activities, and cultural festivals. Autumn brings food events centered on harvest traditions and local flavors.

  • What are the best places to visit in Radicondoli?

    Stroll the historic village center with its stone buildings, visit ancient churches such as the Collegiata dei Santi Simone e Giuda, and explore nearby countryside viewpoints. The town’s cultural spaces often host rotating exhibitions.

  • What are some hiking trails in Radicondoli?

    Radicondoli has walking paths through woodlands, fields, and historic routes connecting nearby hamlets. The area is known for trails with scenic views, wildflowers, and traces of medieval heritage.

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

    Spend time hiking local trails, visiting traditional farms, or joining family-friendly workshops during festivals. The village square is a welcoming place for games, gelato, and mingling with the local community.

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

    Consider exploring neighboring hill towns, visiting Tuscan thermal baths, or discovering medieval castles in the region. Local wineries and artisan producers also invite day visits for tasting experiences.

  • Are there any pet friendly accommodations available in Radicondoli?

    Many vacation rentals and rural estates in Radicondoli welcome guests traveling with pets. Staying amid countryside trails makes it easy for pets and owners to explore outdoors together.

  • What are some local tips for visiting Radicondoli?

    Try local olive oil at a traditional frantoio, visit weekly outdoor markets for fresh produce, and join evening community gatherings when possible. Comfortable shoes are handy for walking stone streets and hills.

  • What is Radicondoli known for?

    Radicondoli is known for its medieval hilltop village, traditional Tuscan landscapes, and locally rooted festivals. Visitors frequently explore its historic architecture, stone streets, and surrounding woodlands.

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

    Look for artisan studios, community gardens, or small chapels tucked around Radicondoli’s old town. Around the village, quiet woodland trails and viewpoints offer a peaceful retreat from busier sights.

  • What are the best foods to try in Radicondoli?

    Local cuisine in Radicondoli features wild boar, hand-rolled pici pasta, and dishes made with seasonal vegetables and olive oil. Traditional cheese, pastries, and local wines are also frequently suggested.

  • What should I bring for a trip to Radicondoli?

    Pack layers for changing temperatures, sun protection for outdoor walks, and comfortable shoes for exploring villages and countryside. A refillable water bottle and camera often come in handy for day trips.

  • What is the nightlife in Radicondoli like?

    Radicondoli's nightlife tends to focus on local cafes, open-air gatherings, and seasonal festivals with music or performances. Evenings are relaxed, with many enjoying leisurely dinners and village events.

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

    Radicondoli has summer music and theater festivals that draw visitors interested in the arts. Food events with local cuisine are also frequently suggested, especially during late summer and autumn.

  • Are there family friendly vacation rentals in Radicondoli?

    Family friendly vacation rentals can be found throughout Radicondoli, including village homes and rural estates with gardens. Larger accommodations and self-catering options are commonly available for groups.

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