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Vacation rentals in Radicondoli

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Top-rated vacation rentals in Radicondoli

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Guest favorite
A charming outdoor area features a wooden table surrounded by vibrant flowers in various pots. A shaded pergola provides a cozy atmosphere, while lush greenery decorates the rustic brick exterior of the structure. Soft sunlight enhances the inviting setting.
Home in Radicondoli

a hideaway in the heart of tuscany

Il Fienile is a completely remodelled old agricultural structure located in one of the most pristine parts of Tuscany, where vines and olive trees join the cypress over the rolling hills of Chianti creating a most unique landscape of rare beauty: kind of a “natural garden”, both domestic and wild, in which every element seems to find its perfect place. The ideal location for an unforgettable romantic vacation, where you can lay back and enjoy the fresh and spacious interior, the shade of the pergola and the scent of the aromatic herbs in the surrounding garden. Where you may visit the nearby artistic cities, take quiet walks in the woods or a gourmet tour of the many trattorias, or even go for a refreshing swim by the seaside or a dive in the crystal clear waters of the local rivers. Grant yourself the luxury of stopping time and break away from the city madness for a while: dine watching the sunset, dream under the starry sky, and restore yourself in this peaceful countryside.The village of Radicondoli is located in one of the most unspoiled regions of Tuscany. Nevertheless Florence and its airport, Siena and some of the main artistic towns of the region, like Colle Val d’Elsa, San Gimignano, Montepulciano, Montalcino, etc., are all located within a 60 km (45 miles) radius. Pisa with its international airport is only 90 km (60 miles) away, while the Etruscan Riviera, with its famous sandy beaches, is only 1 hour away. A pleasant alternative is to bathe in the crystal clear waters of the local rivers, only 10 minutes away from home, or for a highly relaxing experience you may want to treat yourself to the thermal waters of Rapolano, only 50 minutes away. If you’re looking for something else, Radicondoli offers a wide array of choices: walks, hikes, tennis, biking and horse riding, maybe visiting the nearby villages. You may also enjoy the local restaurants, pizzerias, bars and shops, and count on public services (banks, post office, police, pharmacy, etc.).

FamilyLocationWalkability

4.93 out of 5 average rating, 56 reviews
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

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth 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 in your soul. We look forward to welcoming you!

LocationFamilyBreakfast

4.93 out of 5 average rating, 294 reviews
Top guest favorite
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.
Apartment in Radicondoli

SerenaHouse

SerenaHouse is a beautiful residence located in the picturesque medieval village of Belforte, in the municipality of Radicondoli, in the province of Siena. Nestled in the heart of Tuscany, this house offers a small panoramic view of the surrounding hills, ideal for those looking for a quiet and authentic retreat. The village, renowned for the production of extra virgin olive oil and honey, is the perfect place to experience the serenity of the Tuscan countryside, within walking distance of the provinces of Pisa and Grosseto.

ValueLocationDecor

4.96 out of 5 average rating, 50 reviews
Top guest favorite
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.
Apartment in Radicondoli

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.

LocationFamilyKitchen

4.98 out of 5 average rating, 51 reviews
Guest favorite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

FamilyLocationLaundry

4.94 out of 5 average rating, 204 reviews
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

LocationValueAmenities

4.98 out of 5 average rating, 107 reviews
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.
Apartment in Radicondoli

Casa nel cuore di 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.

LocationCheck-inHospitality

5.0 out of 5 average rating, 4 reviews
Guest favorite
Dome in Volterra

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.

FamilyLocationCheck-in

4.95 out of 5 average rating, 189 reviews
Guest favorite
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 in Radicondoli

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.

FamilyLocationOutdoor spaces

4.96 out of 5 average rating, 130 reviews
Top guest favorite
A rustic stone building is set against a backdrop of rolling green hills and olive trees. A shaded pergola is visible in the foreground, offering a space to relax and enjoy the scenic views of the Tuscan countryside.
Farm stay in Radicondoli

Il melograno, 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.

FamilyLocationKitchen

5.0 out of 5 average rating, 33 reviews
Top guest favorite
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.
Apartment in Radicondoli

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.

FamilyLocationDecor

4.96 out of 5 average rating, 51 reviews
Top guest favorite
An original Tuscan stone house is surrounded by lush greenery, with a spacious terrace featuring an umbrella and outdoor seating. Olive trees and lavender bushes are visible, enhancing the natural landscape that envelops the home.
Home in Radicondoli

The Tower

The Torre is an original Tuscan stone house, a so-called "Rustico". It offers a quiet, meditative place, a little away from the village of Radicondoli, in the middle of a natural hilly landscape, a feast for the senses: colors/sounds/smells.

LocationValueHeating

4.98 out of 5 average rating, 58 reviews

Popular amenities for Radicondoli vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Radicondoli

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

AnticaVista, Luxury Apartment with Tower Views

ValueFamilyLong stay

5.0 out of 5 average rating, 70 reviews
Top guest favorite
An aerial view captures the charming layout of the property surrounded by lush greenery, showcasing a spacious pool area with sun loungers. The rustic buildings blend with the natural landscape, and rolling hills stretch into the distance, emphasizing the tranquility of the location.
Vacation home in Sovicille

Podere La Castellina - No. 6 ROSETO

LocationFamilyComfort

4.99 out of 5 average rating, 85 reviews
Guest favorite
Cottage in Colle di Val d'Elsa

Tuscan Rustic with Pool

FamilyLocationParking

4.83 out of 5 average rating, 96 reviews
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

Cipressini 2 - pool and amazing views

FamilyLocationWifi

5.0 out of 5 average rating, 68 reviews
Guest favorite
A serene salt-water pool is framed by lush greenery and vibrant yellow flowers. The pool is uniquely shaped and features a gentle entry with steps. Lounge chairs are positioned nearby, providing a peaceful area for relaxation while enjoying the panoramic views of the Tuscan hills.
Apartment in Radicondoli

Spacious top floor apt. with roof terrace & pool

FamilyValueKitchen

4.89 out of 5 average rating, 55 reviewsThe spacious living area features a modern gray sectional sofa positioned in front of a sleek kitchen. A dining table with black chairs is set nearby, with large windows allowing natural light to illuminate the open space and providing views of the surrounding hills.
Apartment in Pievescola

TuscanView 360: 3 bedr, 2 baths, free parking

FamilyValueWalkability

4.96 out of 5 average rating, 149 reviews
Guest favorite
Villa in Radicondoli

Private Tuscan villa with pool steps from village

FamilyLocationCleanliness

5.0 out of 5 average rating, 11 reviews
Guest favorite
The villa's rustic stone façade is complemented by a spacious outdoor area featuring a private pool. Colorful flowers frame the pool, enhancing the serene environment. The building includes a terrace with multiple chairs and a staircase leading to the upper level, surrounded by rolling hills.
Villa in Radicondoli

Fabulous Villa in the heart of Tuscany

FamilyLocationParking

4.97 out of 5 average rating, 67 reviews

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