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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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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, 153 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
An inviting entrance features wooden doors framed by rustic stone walls. A small wooden table with two chairs is positioned beside it, adorned with potted flowers. A traditional ceramic jar adds character, enhancing the welcoming atmosphere.
Flat
4.96 out of 5 average rating, 47 reviews

SerenaHouse

SerenaHouse è una splendida dimora situata nel pittoresco borgo di medievale di Belforte, nel comune di Radicondoli, in provincia di Siena. Immersa nel cuore della Toscana, questa casa offre una piccola vista panoramica sulle colline circostanti, ideale per chi cerca un rifugio tranquillo e autentico. Il borgo, rinomato per la produzione di olio extravergine di oliva e miele, è il luogo perfetto per vivere la serenità della campagna toscana, a pochi passi dalle provincie di Pisa e Grosseto.

Top guest favourite
A bright living room features a white sofa adorned with decorative pillows, positioned near a large window that opens to a terrace with panoramic views. Natural light floods the space, highlighting the rustic stone wall and simple coffee table with a vase of flowers.
Flat in Radicondoli
4.98 out of 5 average rating, 47 reviews

Tuscan Hilltop Retreat | Views, Charm, Fireplace

Imagine waking up to rolling Tuscan hills, stepping onto your private terrace with a cup of coffee, and realizing you have nowhere else to be. No crowds, no tour buses—just church bells, the fragrance of home‑cooked food, and the peaceful rhythm of an authentic hilltop village. This 14th‑century stone duplex in Radicondoli sits at the heart of a real working village—not a tourist set piece—and puts you within easy reach of Siena, Florence, San Gimignano, and the Chianti wine region.

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, 276 reviews

Casa al Gianni - Hut

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!

Top guest favourite
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
4.99 out of 5 average rating, 475 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 favourite
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.
Flat
4.99 out of 5 average rating, 85 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).

Superhost
A modern living room area is presented with a light gray sofa positioned beside a small wooden coffee table. A kitchen with sleek cabinetry can be seen in the background, while a doorway leads to a bathroom area. Natural light is filtered through the window.
Flat
5 out of 5 average rating, 4 reviews

House in the heart of Radicondoli

Cozy 50 m² holiday home in the heart of the medieval village of Radicondoli, perfect for 2 guests. The apartment, renovated in a modern style, features a bright living room, a bedroom with a queen-size bed, a full bathroom, and a fully equipped kitchen with dishwasher, oven, stovetop, and all necessary appliances. Amenities include high-speed Wi-Fi, TV, washing machine, hairdryer, travel iron and ironing board, bed linen, and towels.

Superhost
A charming stone villa is framed by lush greenery and vibrant flower beds. The building features three arched windows with planters, a terracotta roof, and steps leading to the entrance. The expansive lawn offers a serene atmosphere, complemented by distant views of the rolling hills.
Villa
4.88 out of 5 average rating, 26 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

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, 126 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.

Top guest favourite
A tranquil infinity pool is set against a backdrop of rolling hills, showcasing muted earth tones and green trees. The pool’s water reflects the landscape, while nearby plants frame the scene, adding natural greenery to the view.
Farm stay
5 out of 5 average rating, 28 reviews

The cherry tree, Podere il giglio

Podere il Giglio is a small farmhouse surrounded by 3 hectares of olive trees, it enjoys a lovely view 'il ciliegio', can accommodate a maximum of4 people. Apartment on the ground floor with indipendent entrance: living room with fireplace and kitchen, 2 bedrooms, 2 bathrooms with shower, outdoor and a private gazebo. In the property there is a private pool (5x10mt).

Guest favourite
An outdoor seating area features two red armchairs positioned around a small table, accompanied by potted plants. The entrance to the living space is framed by wooden doors, and a charming cobblestone street is visible, lined with buildings in warm tones.
Flat
5 out of 5 average rating, 12 reviews

Radicondoli House

The holiday apartment Radicondoli House is located in the historical center of Radicondoli Siena and is perfect for an unforgettable holiday with your loved ones. The 85 m² property consists of a living room with a sofa bed for 2 people, a fully-equipped kitchen with a dishwasher, 1 bedroom and 2 bathrooms and can therefore accommodate 4 people.

Top guest favourite
A rustic stone building is set against a clear blue sky, featuring arched windows and a slate roof. The surrounding landscape includes a gravel pathway and green trees, contributing to a serene ambiance.
Flat
4.96 out of 5 average rating, 47 reviews

Apartment in Old Farmhouse

My accommodation is close to the city center, panoramic views, art and culture, restaurants and parks. My accommodation is suitable for couples, lone adventurers, families and to all lovers of beauty. Air conditioning is installed in the main room, and professional fans are installed in the other rooms.

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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