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Holiday houses 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 in Asciano
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.

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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 in Geggiano
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.

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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.
Apartment in Radicondoli
4.96 out of 5 average rating, 46 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.

LocationFamilyIndoor spaces

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.
Condo in Pienza
5 out of 5 average rating, 149 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?

LocationFamilyWi-Fi

Top Guest favourite
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
5 out of 5 average rating, 52 reviews

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.”

ValueFamilyQuiet

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 in Simignano
4.92 out of 5 average rating, 272 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!

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Guest favourite
An outdoor seating area features a small round table surrounded by two red folding chairs. A wooden bench with a cushioned seat is positioned nearby. Potted olive trees add greenery, while stone walls provide a rustic backdrop, creating a tranquil space for relaxation.
Apartment in Radicondoli
4.93 out of 5 average rating, 29 reviews

Radicondoli Studio

The studio apartment 'Radicondoli' is located in the historical centre of Radicondoli Siena and is perfect for an unforgettable holiday with your loved ones. It has a small balcony for beautiful views and in the entrance of the outdoor area there is an armchair and a small table to chill outside. The 45 m² property consists of a living room with a sofa bed for one person, a fully-equipped kitchen and 1 bathroom and can therefore accommodate 3 people.

LocationGetting aroundSleep quality

Guest favourite
A spacious kitchen is presented with rustic wooden beams and terracotta tiles. It features a decorative backsplash with vibrant tiles, an extensive countertop, and ample cabinetry. A large dining table with wooden chairs occupies one side of the room, with windows allowing natural light and a view of the landscape.
Apartment in Radicondoli
4.9 out of 5 average rating, 49 reviews

Spacious top floor apt. with roof terrace & pool

The VILLA CASA RIPI is situated between Siena and San Gimignano 5 km far from the ancient village Radicondoli. Quiet but not remote, located in one of the most panoramic landscape in the hart of Tuscany and cultural richest area Italy. The farmhouse from the 10th century was restored recently lavish in typical medieval natural stone design. The location gives our guests peace and natural experiences in its purity with grandiose panoramic view.

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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 in Radicondoli
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.

FamilyLocationHot tub

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 in Radicondoli
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.

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Top Guest favourite
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
5 out of 5 average rating, 27 reviews

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.

LocationFamilyComfort

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.
Apartment in Radicondoli
4.96 out of 5 average rating, 46 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.

LocationFamilyPool

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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