Vacation rentals in Radda in Chianti

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.

Family · Value · TV

1500 Stone House in Chianti Heart private lake B

Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets of Chianti Classico Wine as you reside in a meticulously restored ancient farmhouse from the 1500s. We strive to offer an authentic experience that resonates with the charm of the past, within a breathtaking natural oasis as in a small paradise. 2005-2026 We have been hosting for 21 years,and guests have come from 67 different countries: we have been Superhost for 11 years.

Value · Location · Bathroom

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Family · Location · Laundry

Selvabella in Chianti B&B. Lo Scricciolo Suite

Tower accommodation with a private entrance through an exclusive loggia with panoramic views. The first floor features a living room with a tower fan and a small pantry area (not a kitchen) for preparing a light meal or coffee. A staircase leads to the second floor, where there is an air-conditioned (AC) bedroom with a double bed and a sofa bed. The room includes a shower and private bathroom. Please note: three flights of stairs connect the parking area to the accommodation.

Family · Value · Cleanliness

The 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.

Location · Family · Accuracy

The Chianti Cabin

Rustic Tuscan-style apartment located in the heart of Chianti, just outside the historic center of Radda. The recently renovated accommodation is equipped with: · 1 bedroom with two single beds or a double bed (guest's choice) · 1 bedroom with a double bed · 1 crib · 1 bathroom · Free wifi (fiber optics) · Equipped kitchen and coffee machine · Washer-dryer · Living room with 43" Smart TV · Shared outdoor garden with table and umbrella for exclusive use

Value · Family · Kitchen

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Location · Family · Wifi

Casa Dante – Authentic Chianti Stay | Views & Relaxation

Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Value · Family · Cleanliness

Chianti La Pruneta, Raphael Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

Value · Location · Pets

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Location · Value · Checkout

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.

Location · Kitchen · Parking

Villa le Scope 5*

Villa le scope is located in the heart of Chianti, surrounded by nature and tranquility, yet just a short walk from the village. You can taste an excellent Chianti Classico wine on the beautiful terrace or in total relaxation in our large garden. Villa le Scope is about an hour from Florence and half an hour from Siena.

Location · Family · Check-in