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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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Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 352 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

ValueFamilyView

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, 50 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.

LocationValueAir conditioning

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.
Apartment in Radicondoli
4.98 out of 5 average rating, 50 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.

LocationFamilyQuiet

Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 198 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

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Top Guest favourite
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
4.98 out of 5 average rating, 107 reviews

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.

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Guest favourite
Apartment in Radicondoli
5.0 out of 5 average rating, 14 reviews

Monolocale Antico Fienile

Open Space Antico Fienile in Radicondoli is a welcoming open-plan apartment nestled in the peaceful Tuscan hills, perfect for a relaxing, nature-filled holiday. The accommodation features a bright living area with a fully equipped kitchen, lounge with sofa and TV, sleeping area with a double bed, and a charming mezzanine with a second double bed. There is also a bathroom with a shower cabin. The apartment accommodates up to 2 adults and 2 children.

LocationFamilyGetting around

Guest favourite
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
4.94 out of 5 average rating, 203 reviews

Country cottage C&M immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

LocationFamilyComfort

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
4.89 out of 5 average rating, 27 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.

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Guest favourite
Dome in Volterra
4.95 out of 5 average rating, 185 reviews

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.

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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
4.96 out of 5 average rating, 130 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.

FamilyValueCleanliness

Superhost
The typical stone house is showcased alongside a private swimming pool. A spacious terrace with balcony extends from the front of the building, surrounded by landscaped greenery and hills in the background. Blue skies with scattered clouds enhance the serene outdoor setting.
Apartment in Radicondoli
4.7 out of 5 average rating, 30 reviews

House 7 mins walk to center w/ private pool

This typical stone house is situated in a panoramic position about 200 m. from Radicondoli, a characteristic and attractive mediaeval village (population 1.000) situated in a hilly position about 45 km from Siena. Guests can therefore avail of all the facilities available in Radicondoli ( food shops, restaurants, bank, tennis-court, etc.) without having to use the car.

FamilyLocationNearby

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
5.0 out of 5 average rating, 33 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.

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Popular amenities for Radicondoli holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Radicondoli

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
5.0 out of 5 average rating, 4 reviews

Casa nel cuore di Radicondoli

LocationGetting aroundCheck-in

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
4.89 out of 5 average rating, 55 reviews

Spacious top floor apt. with roof terrace & pool

ValueLocationComfort

Top Guest favourite
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.
Holiday home in Sovicille
4.99 out of 5 average rating, 85 reviews

Podere La Castellina - N°6 ROSETO

LocationFamilyCheck-in

Top Guest favourite
An outdoor seating area is shaded by a fabric canopy, featuring a comfortable long bench with decorative pillows and a dining table surrounded by metal chairs. Colorful flower pots filled with blooming flowers enhance the garden's vibrant atmosphere, set against a rustic stone wall.
Apartment in Colle di Val d'Elsa
5.0 out of 5 average rating, 80 reviews

CANONICA 43 Luxury villa in the heart of Tuscany

ValueFamilyLong stay

The 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
4.96 out of 5 average rating, 149 reviews

TuscanView 360: 3 bedr, 2 baths, free parking

FamilyLocationOutdoor spaces

Guest favourite
Villa in Radicondoli
5.0 out of 5 average rating, 11 reviews

Private Tuscan villa with pool steps from village

LocationFamilyWalkability

Guest favourite
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
4.97 out of 5 average rating, 67 reviews

Favolosa Villa nel cuore della Toscana

ValueLocationBathroom

A serene swimming pool is set in a spacious outdoor area, surrounded by lush greenery and gentle hills. Sun loungers and umbrellas provide shaded relaxation, while the distant hill showcases a small town. A shaded seating area enhances the peaceful atmosphere of the landscape.
Farm stay in Radicondoli
5.0 out of 5 average rating, 4 reviews

Casale toscano agro-biologico

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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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