
Holiday rentals 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.

Tuscan House with Private Jacuzzi in Chianti
An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

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.

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 - 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!

Luxury Medieval Tower • Exclusive Chianti Stay
Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

La Casina. Nel cuore di Belforte
La Casina si trova nel cuore di Belforte, incantevole borgo toscano risalente al 1180, posto al limitare della Riserva Naturale Di Popolamento Animale di Cornocchia e a breve distanza dall'Abbazia di San Galgano, San Gimignano, Volterra e Siena, dal mare di Follonica e da Firenze. E' fornita di piano a induzione, frigorifero e congelatore, lavastoviglie, lavatrice e asciugatrice. Grazie a questo spazio in posizione strategica, non dovrai rinunciare a nulla.

Live the Tuscany Experience in Our Country House
An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

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.

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.

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.

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.

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.
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

TuscanView 360: 3 bedr, 2 baths, free parking

a.d. 1237

Casa nel cuore di Radicondoli

LA CASA NUOVA- Apartment in farm house with pool

Favolosa Villa nel cuore della Toscana
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 a washing machine and dryer Radicondoli
- Rentals with a fireplace Radicondoli
- Rentals with pools Radicondoli
- Flat rentals Radicondoli
- Rentals with outdoor seating Radicondoli
- House rentals Radicondoli
- Family-friendly rentals Radicondoli
- Rentals with a patio Radicondoli
- Pet-friendly rentals Radicondoli
- Villa 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
- Mercato Centrale
- Pisa Centrale Railway Station
- Parco Regionale Della Maremma
- Uffizi Gallery
- Fortezza da Basso
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Spiagge Bianche
- Piazzale Michelangelo
- Spiaggia Di Sansone
- Parco delle Cascine
- Gulf of Baratti
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden
- Palazzo Vecchio





