Some info is shown in its original language. Translate
Become a host

Vacation rentals in Radda in Chianti

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Radda in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Guest favorite
The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.
Home in Greve in Chianti
4.95 out of 5 average rating, 103 reviews

Agriturismo Casa Giulia di Sopra

L'appartamento CASA GIULIA DI SOPRA, ristrutturato nel 2022 e situato al primo piano, è una porzione di un'antica colonica situata nel cuore del Chianti Classico. E' circondato dai vigneti di Villa Calcinaia, tenuta di proprietà dei Conti Capponi dal 1524. L'appartamento si trova a 130 mt. di distanza dalla piscina condivisa, aperta da maggio ad ottobre.L'appartamento dispone di un'area esterna dotata di tavolo e sedie dove gli ospiti potranno desinare e godersi un bicchiere di vino al tramonto.

LocationFamilyHospitality

Guest favorite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.93 out of 5 average rating, 254 reviews

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

LocationFamilyKitchen

Guest favorite
A serene bedroom features two single beds that can be combined into a double, complemented by soft pillows and warm bedding. Natural light filters through the window, adorned with patterned curtains. Rustic decor includes wooden accents and artwork on the walls, enhancing the inviting atmosphere.
Apartment in Radda in Chianti
4.97 out of 5 average rating, 63 reviews

La Capannina del Chianti

Appartamento rustico in stile toscano situato nel cuore del Chianti, appena fuori dal centro storico di Radda. L'alloggio, recentemente ristrutturato, è dotato di : · 1 camera con due letti singoli o un letto matrimoniale (a scelta dell'ospite) · 1 camera con letto matrimoniale · 1 culla · 1 bagno · Wi-Fi gratuito (fibra ottica) · Cucina accessoriata e macchina del caffè · Lavasciuga · Soggiorno con Smart TV da 43" · Giardino esterno condiviso con tavolo ed ombrellone ad uso esclusivo

FamilyValueView

Top guest favorite
Home in Greve in Chianti
4.99 out of 5 average rating, 113 reviews

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

LocationValuePool

Guest favorite
Home in Barberino Tavarnelle
4.96 out of 5 average rating, 47 reviews

splendida colonica nel chianti giardino panoramico

“DIMORA BADIA A PASSIGNANO” Vivrete un soggiorno rilassante e ristorativo nel cuore del chianti classico. soggiornerete in un antico fienile totalmente restaurato in pietra con grande giardino recintato e un antico gazebo, adatto a gruppi numerosi e famiglie. le camere sono comode e spaziose per 8 persone. la ristrutturazione è stata eseguita finemente, tenendo conto di ogni minimo particolare estetico per poter farvi respirare l’antica tradizione toscana mixata con la comoda modernità.

FamilyLocationSleep quality

Top guest favorite
Home in Il Poggetto
4.93 out of 5 average rating, 152 reviews

La Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

ValueLocationIndoor spaces

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
4.98 out of 5 average rating, 105 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.

ValueFamilyComfort

Top guest favorite
A welcoming living area is featured with an orange sofa complemented by two decorative cushions. A large piece of artwork hangs above the couch, while a stone wall adds texture. A potted plant and a wooden console table enhance the room's natural elements.
Condo in Greve in Chianti
4.98 out of 5 average rating, 195 reviews

Il Nido nel Chianti

Ci teniamo ad informare che per questa emergenza stiamo facendo tutto il possibile per aiutare e proteggere i nostri ospiti adottando una dettagliata e rigida pulizia, disinfettando e sanificando tutte le parti della casa. Accogliente appartamento, finemente ristrutturato in pieno centro storico al secondo piano con affaccio sulla bella piazza di Greve in Chianti. Nella sua terrazza condominiale potrete trascorre splendidi momenti di relax.

LocationFamilyGetting around

Guest favorite
A stone bungalow is viewed from the poolside, featuring a private pool surrounded by sun loungers and an umbrella. The terrace, equipped with a dining table and chairs, shows lush greenery and elegant flowers in window boxes.
Villa in Radda in Chianti
5.0 out of 5 average rating, 10 reviews

La Casa di Radda

La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming village of Radda. Just a short walk separates the house from the delightful restaurants, cafés, and small shops in the town center. It is ideal for a family vacation or a getaway with friends, offering the perfect setting for relaxing days in a rural environment.

ValueFamilyOutdoor spaces

Guest favorite
Condo in Radda in Chianti
4.95 out of 5 average rating, 20 reviews

Appartamento Holly House

Intero appartamento, un letto matrimoniale e un comodo divano letto, su richiesta una culla per bebè. • Un ampio parcheggio gratuito • Una cucina accessoriata • Un resede privato, con divano e tavolo da pranzo. •Wi-FI gratuito. • Aria condizionata • Riscaldamento • Bagno con doccia e bidet • Distanza solo 500m dal centro storico di Radda in Chianti.

LocationAccuracyEV charging

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
5.0 out of 5 average rating, 65 reviews

Cipressini 2 - piscina e vista mozzafiato

Ancient stone farmhouse adjacent to the main farmhouse dating back to the 17. century, located in the heart of the Chianti Classico on the side of a slope with breathtaking views over the Val d'Elsa. Luxuriously renovated and furnished, equipped with every comfort, it is located in such a way as to guarantee absolute privacy.

LocationFamilyAir conditioning

Guest favorite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti
4.98 out of 5 average rating, 49 reviews

Villa le Scope 5*

Villa le scope si trova nel cuore del Chianti, in mezzo alla natura e alla tranquillità, pur essendo a pochi passi dal paese. Potrai degustare un ottimo vino Chianti Classico, sulla bellissima terrazza o in totale relax nel nostro grande giardino. La villa le Scope dista un ora circa da Firenze e mezz'ora da Siena.

FamilyLocationIndoor spaces

Popular amenities for Radda in Chianti vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Radda in Chianti

Guest favorite
A pleasant backyard space features a well-maintained lawn and a flowering tree. A stone pathway leads to a seating area with a table and chairs, inviting outdoor dining. The house's exterior is characterized by warm-toned walls and brown window shutters.
Home in Radda in Chianti
4.84 out of 5 average rating, 38 reviews

Casa a schiera nel Chianti

FamilyLocationAccess

Guest favorite
A window framed by white trim offers a view of rolling green hills, dotted with trees and vines. Overcast skies create a serene atmosphere, while a garden filled with shrubs is visible at the base of the window.
Apartment in Radda in Chianti
5.0 out of 5 average rating, 22 reviews

Tuscany Chianti Village Experience

FamilyLocationDecor

Guest favorite
The historic farmhouse is surrounded by tall, ancient cypress trees and lush greenery. A gravel patio with outdoor seating is visible in the foreground, leading to an inviting garden area. The sky is clear with scattered clouds, creating a bright and welcoming ambiance.
Vacation home in Radda in Chianti
4.98 out of 5 average rating, 46 reviews

Tuscany Country House, Central Chianti, Pano Views

ValueLocationGetting around

Top guest favorite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti
4.99 out of 5 average rating, 74 reviews

Sestuccia

LocationFamilyGetting around

Guest favorite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

LocationFamilyIndoor spaces

Top guest favorite
A spacious bedroom features a four-poster bed draped with soft fabric. Two bedside lamps create gentle illumination. An arched bookshelf filled with books is visible in the background, alongside a cozy seating area with upholstered chairs, highlighting a mix of comfort and elegance.
Villa in Panzano in Chianti
4.93 out of 5 average rating, 94 reviews

Luxury Villa on Chianti Wine Estate

LocationValueCleanliness

Top guest favorite
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Apartment in Quercegrossa
4.98 out of 5 average rating, 82 reviews

Tuscany jem: La Casa del Fattore del Chianti

LocationFamilyQuiet

Guest favorite
Apartment in Cavriglia
4.95 out of 5 average rating, 40 reviews

Apartment Comfort | Quiet Escape in Tuscany

LocationValueAmenities

Frequently Asked Questions

  • What are the best places to stay in Radda in Chianti?

    Stay in vacation rentals or agriturismo settings across Radda in Chianti, ranging from village apartments to countryside villas. Many accommodations have easy access to local food, walking trails, and cultural sites.

  • What are the best things to do in Radda in Chianti with kids?

    Radda in Chianti has family-friendly walking trails, hands-on workshops at local farms, and gelato tastings in the village. Children often enjoy watching grape harvest activities and exploring castles around the area.

  • What are some of the best things to do in Radda in Chianti?

    Explore historic streets in Radda in Chianti, visit local wineries, and enjoy panoramic views from nearby hilltops. The area has traditional restaurants, artisan shops, and medieval sites for a mix of cultural and culinary experiences.

  • How is the weather in Radda in Chianti?

    Radda in Chianti has cool, wetter winters around 33–49°F (0–9°C), and warm, drier summers near 60–89°F (16–32°C). Spring and autumn bring mild temperatures and lush landscapes, ideal for exploring outdoors.

  • When is the best time to visit Radda in Chianti?

    Late spring is often recommended for bright landscapes and mild afternoons near 74°F (23°C). Early autumn draws visitors with vineyard harvests and lively local festivities, set against cooler days around 68°F (20°C).

  • What are the best places to visit in Radda in Chianti?

    Explore the historic village center, visit traditional wineries, and wander through local artisan markets in Radda in Chianti. Medieval churches and scenic countryside make for enjoyable stops throughout the area.

  • What are some hiking trails in Radda in Chianti?

    Radda in Chianti has scenic trails winding through vineyards, forests, and along historical routes. Many routes feature gentle hills and panoramic views, making them accessible for a range of experience levels.

  • What are some family activities we can do in Radda in Chianti?

    Families can explore walking trails, take part in hands-on cooking classes, or enjoy interactive visits to vineyards and farms in Radda in Chianti. Gelato shops and markets around the village are popular with all ages.

  • What are some of the best day trip ideas from Radda in Chianti?

    Day trips often include exploring medieval villages, visiting renowned wineries, or hiking in surrounding Tuscan hills. Historic sites, local food markets, and artisan workshops around the region are frequently suggested.

  • Are there any pet friendly accommodations available in Radda in Chianti?

    Many accommodations around Radda in Chianti welcome pets, including vacation rentals and rural stays. Green spaces and walking paths make it easier to enjoy the area with your animal companions.

  • What are some local tips for visiting Radda in Chianti?

    Bring comfortable shoes for wandering village streets and vineyard paths, and sample locally made olive oil or wine. Early mornings offer quieter views, and many visitors appreciate learning a few Italian phrases for connecting with residents.

  • What is Radda in Chianti known for?

    Radda in Chianti is known for its locally rooted wine culture, preserved medieval architecture, and scenic countryside dotted with vineyards. The area has traditional festivals and culinary experiences that highlight Tuscan heritage.

  • What are the best hidden gems to explore in Radda in Chianti?

    Radda in Chianti has tucked-away artisan studios, scenic vineyard paths, and lesser-known local trattorias serving regional specialties. Some visitors enjoy discovering quiet chapels and small historical sites nestled within the village.

  • What are the best foods to try in Radda in Chianti?

    Radda in Chianti has locally made wines, pecorino cheese, wild boar pasta, and freshly baked bread. Olive oil tastings and gelato from village shops are frequently suggested by visitors.

  • What should I bring for a trip to Radda in Chianti?

    Pack layers for cooler evenings, comfortable walking shoes, and a reusable water bottle. If you plan to visit vineyards or the countryside, sunscreen and a hat are often recommended during warmer months.

  • What is the nightlife in Radda in Chianti like?

    Nightlife in Radda in Chianti centers on relaxed wine bars, trattorias, and occasional live music in local venues. Evening strolls and small village squares create a laid-back, sociable atmosphere.

  • What are the most popular events or festivals in Radda in Chianti?

    Radda nel Bicchiere is frequently suggested for wine tastings in early summer, and Festa del Perdono brings the community together with music, food, and cultural activities in early autumn. Both events are rooted in local traditions and highlight the region’s wine culture.

  • Are there family friendly vacation rentals in Radda in Chianti?

    Radda in Chianti has many family-friendly vacation rentals, including spacious villas and apartments in the village or countryside. Typically, these stays feature easy access to outdoor spaces and local attractions.

Destinations to explore