
Holiday houses in Radicondoli
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Top-rated holiday rentals in Radicondoli
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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.

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.

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.

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.”

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!

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.

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.

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.

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.

Casa delle Rose
Casa delle Rose – Relaxing Holiday Two-storey house with a spacious and comfortable living area, a large bedroom and an en suite bathroom. Belonging to the property is a large terrace, where you can relax and enjoy breakfast at first light, feeling magically surrounded by nature. Here, you can enjoy the silence and peace you need to rediscover harmony. Private parking and entrance.

The pomegranate, Podere il Giglio
Podere il Giglio is a small farmhouse surrounded by 3 hectares of olive trees, it enjoys a lovely view . At guests' disposal there is an indipendent house 'il melograno', that can accommodate 4 people: living room with fireplace, kitchen, 2 bathrooms with shower and 2 bedrooms. Outdoor and a private gazebo. In the Podere there is a 5mt x 10 mt pool.

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.
Popular amenities for Radicondoli holiday rentals
Other great holiday rentals in Radicondoli

Villa in Tuscany Top Location View 1' Walk to Town

Luxury Medieval Tower - Penthouse

La Casina. In the heart of Belforte

Penthouse in small medieval castle near Florence

Luxury Medieval Tower • Exclusive Chianti Stay

Relax in Tuscany Country Home with a Stunning View

Palazzina Maresa - Loft 4

Spacious top floor apt. with roof terrace & pool
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.
Destinations to explore
- Rentals with outdoor seating Radicondoli
- Family-friendly rentals Radicondoli
- Apartment rentals Radicondoli
- Rentals with pools Radicondoli
- Rentals with a washing machine and dryer Radicondoli
- Pet-friendly rentals Radicondoli
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- Rentals with a patio Radicondoli
- Rentals with a fireplace Radicondoli
- House rentals Radicondoli
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Piazza della Repubblica
- Spiagge Bianche
- Parco delle Cascine
- Spiaggia Di Sansone
- Del Chianti
- Piazzale Michelangelo
- Gulf of Baratti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria





