Radda in Chianti Rentals
From $270 per night (USD)VRBO
Home 'Serena, Radda In Chianti' with Private Pool, Private Terrace and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Radda in Chianti, the holiday home Casa Serena, Radda In Chianti has everything you need for a relaxing holid ...
From $270 per night (USD)VRBO
From $691 per night (USD)VRBO
Villa Pozzo della volpe
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Nestled in the heart of the picturesque Greve in Chianti, this family-friendly villa offers a tranquil oasis for your ne ...
From $691 per night (USD)VRBO
From $492 per night (USD)VRBO
Beautiful villa for 12 people with WIFI, private pool, TV, balcony, pets allowed and panoramic ...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Property Summary Il Poggio is a beautiful farmhouse divided into three residential units, offering the option to book tw ...
From $492 per night (USD)VRBO
From $764 per night (USD)Expedia
Casa Faraona, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Faraona is located in the heart of the Chianti Classico and is a spacious holiday home, ideal for a relaxing holida ...
From $764 per night (USD)Expedia
From $1027 per night (USD)VRBO
Stunning private villa with private pool, WIFI, TV and patio, close to Greve In Chianti
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Villa Poggio La Croce is a beautiful stone building (400 sq m) with private pool and WiFi internet. The property can ac ...
From $1027 per night (USD)VRBO
From $789 per night (USD)Expedia
Stunning private villa for 16 people with private pool, A/C, WIFI, TV and veranda, close to Siena
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Villa Tregole is located 3 km (2 mi) from Fonterutoli, Italy and only 21 km (13 mi) from Siena in the tourist area "Sien ...
From $789 per night (USD)Expedia
From $944 per night (USD)VRBO
Villa W/Infinty Pool Villa in the Heart of Chianti
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
<p>Located in Castellina in Chianti, this 5-bedroom, 4-bathroom villa lets you experience it all. Fans of nature and the ...
From $944 per night (USD)VRBO
From $102 per night (USD)Expedia
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The apartment Al Poggio Della Capannina in Castellina in Chianti is the perfect accommodation for a stress-free holiday ...
From $102 per night (USD)Expedia
From $122 per night (USD)VRBO
Apartment 'Tuscan Style , Shared Pool' with Shared Pool, Private Garden and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Located in Gaiole In Chianti, the holiday apartment Tuscan Style , Shared Pool has everything you need for a comfortable ...
From $122 per night (USD)VRBO
From $1574 per night (USD)Expedia
Luxury Villa W/ Panoramic Views & Private Pool
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
<p>Located in Castelnuovo Berardenga, this 7-bedroom, 7-bathroom villa lets you experience it all. Fans of nature and th ...
From $1574 per night (USD)Expedia
From $1208 per night (USD)VRBO
Charming Villa W/ Private Pool in Heart of Chianti
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 8
<p>Nestled in Radda in Chianti, this 8-bedroom, 4-bathroom villa brings it all within your reach. Fans of nature and the ...
From $1208 per night (USD)VRBO
From $1521 per night (USD)Expedia
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this marvelous typical Tuscan stonehouse in picturesque Radda in Chianti. With 4 cozy bedrooms including 1 que ...
From $1521 per night (USD)Expedia
From $175 per night (USD)VRBO
Apartment Fonterutoli
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
'recently renovated apartment located in a medieval village between Siena and Castellina in Chianti Località Fonterutoli ...
From $175 per night (USD)VRBO
From $184 per night (USD)Expedia
Typical apartment in Chianti Classico with Wi-Fi and A/C just a stone's throw from Siena
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
<p>Located in Radda in Chianti, this welcoming vacation home brings it all within your reach. With convenient onsite par ...
From $184 per night (USD)Expedia
From $4335 per night (USD)VRBO
My Rental Homes - Villa Torre del Chianti with hited pool, Gym and wellness center
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Villa Torre del Chianti is a unique property in the heart of the Chianti reagion in Tuscany, a step away from Radda in C ...
From $4335 per night (USD)VRBO
From $143 per night (USD)Expedia
Apartment 'Cipressaia Botticelli' with Shared Pool, Private Terrace and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The holiday apartment Agriturismo Cipressaia Botticelli in Greve in Chianti is the perfect accommodation for a stress-fr ...
From $143 per night (USD)Expedia
From $142 per night (USD)VRBO
Apartment 'Cipressaia Bellavista' with Shared Pool, Shared Garden and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The holiday apartment Agriturismo Cipressaia Bellavista is located in Greve in Chianti and is perfect for an unforgettab ...
From $142 per night (USD)VRBO
From $225 per night (USD)Expedia
Apartment 'Il Magnifico' with Shared Pool, Private Terrace and Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Greve in Chianti, the holiday apartment Agriturismo Cipressaia Il Magnifico has everything you need for a com ...
From $225 per night (USD)Expedia
From $519 per night (USD)VRBO
Historic farmhouse in San Donato in Perano, Gaiole in Chianti, with shared pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Historic farmhouse dating back to the year 1000, between Gaiole in Chianti and Radda in Chianti with shared swimming poo ...
From $519 per night (USD)VRBO
From $415 per night (USD)Expedia
La Pesa di Mezzo, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
La Pesa di Mezzo is a beautifully restored Tuscan barn set in the heart of the unspoilt Chianti countryside.The property ...
From $415 per night (USD)Expedia
From $255 per night (USD)VRBO
Stunning private villa with WIFI, A/C, TV and panoramic view, close to Greve In Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Property Villetta Cafaggio, Ac, Wifi, Panzano In Chianti is a lovely stone building (110 sq m) that includes WiFi inter ...
From $255 per night (USD)VRBO
From $132 per night (USD)Expedia
Romantic Apartment In Chianti Classico, Castelnuovo Berardenga, Italy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore the Chianti hills and vineyards from Romantic Apartment, a charming apartment for 2 in the heart of Tuscany. On ...
From $132 per night (USD)Expedia
From $168 per night (USD)VRBO
La Capannina del Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Located in Radda in Chianti, this welcoming apartment lets you experience it all. With convenient onsite parking, you ...
From $168 per night (USD)VRBO
From $429 per night (USD)Expedia
Farmhouse in Chianti with Pool and Garden
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This magnificent farmhouse is located in one of the most beautiful areas of Tuscany. Chianti, famous throughout the worl ...
From $429 per night (USD)Expedia
From $314 per night (USD)VRBO
Campo Agli Olivi, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 4
Campo Agli Olivi is a charming Tuscan stone villa nestled in the gentle hills of the Chianti region, offering two indepe ...
From $314 per night (USD)VRBO
From $126 per night (USD)Expedia
Amazing home in Greve in Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Look forward to relaxing days in this attractive holiday home with an outdoor hot tub. In this historic house you can ...
From $126 per night (USD)Expedia
From $459 per night (USD)VRBO
Wonderful villa for 10 guests with A/C, WIFI, TV, patio and panoramic view
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Property Summary 'Terrazza sul Chianti' is a large, modern two-story house renovated in 2025, situated in Castellina In ...
From $459 per night (USD)VRBO
From $646 per night (USD)Expedia
Panoramic Chianti Villa with Private Pool & SPA - Castellare Petroso
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Castellare Petroso, where the Tuscan dream comes to life. This magnificent villa is located in the heart of C ...
From $646 per night (USD)Expedia
From $125 per night (USD)VRBO
Casetta Maestrini, secciano loc. no. 49, Monti del Chianti, Cavriglia ( Arezzo).
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to ecotours, cycling, and more, this smoke-free vacation home brings it all within reach. Jump into your car an ...
From $125 per night (USD)VRBO
From $1891 per night (USD)Expedia
Muricciaglia 14, Emma Villas
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
This rate includes: -Utilities: Electricity, water, gas for cooking purposes - weekly linen, initial and final cleaning ...
From $1891 per night (USD)Expedia
From $397 per night (USD)VRBO
Terrazza sul Chianti by Interhome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Castellina in Chianti: Large, modern house "Terrazza sul Chianti", 2 storeys, renovated in 2025. 2 houses in the residen ...
From $397 per night (USD)VRBO
From $231 per night (USD)VRBO
Spacious, rustic two-story apartment with Chianti views and loggia
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>A short distance from horse riding, winery tours, and more, this pet-friendly vacation home lets you experience it al ...
From $231 per night (USD)VRBO