
Holiday houses in Radicondoli
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Radicondoli
Guests agree: these stays are highly rated for location, cleanliness and more.

Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Podere La Castellina - No. 2 LECCETO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

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.

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.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

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.

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Casale Santa Barbara - Exclusive Apartment
Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.
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

Open Space Piscina e Giardino

Casa delle Rose

House in the heart of Radicondoli

LA CASA NUOVA- Apartment in farm house with pool

Japandi apartment with a view!

Fabulous Villa in the heart of Tuscany
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
- Family-friendly rentals Radicondoli
- Pet-friendly rentals Radicondoli
- Villa rentals Radicondoli
- Rentals with pools Radicondoli
- Rentals with a fireplace Radicondoli
- Rentals with a washing machine and dryer Radicondoli
- Rentals with a patio Radicondoli
- Apartment rentals Radicondoli
- House rentals Radicondoli
- Rentals with outdoor seating Radicondoli
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Mercato Centrale
- Uffizi Gallery
- Piazza della Repubblica
- Fortezza da Basso
- Piazzale Michelangelo
- Spiaggia Di Sansone
- Spiagge Bianche
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Spiaggia Di Barbarossa
- Parco delle Cascine
- Spiaggia di Capo Bianco
- Gulf of Baratti
- Medici Chapel





