Apartment holiday rentals in Gaiole in Chianti

House of Delights - The Medici private leisure house

La Casa di Delizie, a luxurious retreat nestled in a historic guard tower dating back to the Middle Ages, once cherished by the Medici family. Adorned with the exquisite fresco "Caduta di Icaro," this exclusive apartment seamlessly blends rich history with contemporary luxury. Ideally located on Via Orti Oricellari, just 150 meters from the main train station, it provides effortless access to Florence's treasures. Indulge in bespoke experiences and refined amenities for an unforgettable escape!

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

[Ponte Vecchio] Charm and Awesome view of Florence

Make your stay unique and treat yourself to an experience that you will carry within you for a lifetime. Located in the heart of Florence, this magnificent apartment is the ideal solution for those looking for an exclusive and prestigious site to combine with a central location, which is perfect for easily visiting the main sites of interest, all reachable in less than 10 minutes by foot. The views are on Ponte Vecchio, and you can enjoy one of the most fascinating panoramas of the city.

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Apartment in Chianti at Mulino dell'Argenna

The apartment of the Roses is located inside the Mulino dell'Argenna guest house. The property was completely restored in 2015. It is an ancient stone mill dating back to 1400, built along the course of the Borro dell'Argenna. The Mill is an enchanting place, surrounded by the greenery of the forest, with a beautiful one-hectare park and a large swimming pool. An ideal place to spend your days in Tuscany in maximum privacy, in full contact with nature.

At Paola's in Chianti

My apartment is located in the village of Villa a Sesta, on the ground floor with direct access to the garden, has two bedrooms, one double, the other with bunk beds, two bathrooms, a large kitchen and a living room. The outdoor space is very large and the garden has a large table and armchairs for relaxation, the car can be parked at home, we have a private parking space, arriving in the village you access the house from a small white road (30mt).

💜 "Ilary" Le Fontanelle Farmhouse

Imagine staying in a typical stone house in the Tuscan countryside, surrounded by nature, just 1 km from the village of Radda in Chianti, and being able to look out every day on a breathtaking panorama that will offer you enchanting sunsets. -70m2 -conceived panoramic outdoor patio - TV with Google TV -covered private parking -shared pool (June 1 - September 15) -heating (November 1 - April 1) -wifi -kitchen

Casa Ricci Apartment in a 14th-century building

Our apartment is located a few meters from Piazza Grande, sleeps up to 4 people and overlooks a beautiful view. It was recently renovated and is located in a historic building from the 1300s. Our apartment is located a few meters from Piazza Grande, it sleeps up to 4 people and overlooks a beautiful view. It was recently renovated and is located in a historic building from the 1300s.

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

La Casina

Recently renovated, a stone's throw from the historic center of Radda in Chianti, with a supermarket and bank 100 m away, 70 sqm apartment with private entrance, large living room with double sofa bed, kitchen, double bedroom, bathroom with shower, outdoor loggia, and adjacent parking.

Casa Pieralli in the Historic Chianti

Small but cozy two-room apartment in the heart of Gaiole in Chianti. Absolutely quiet and peaceful area in the historic center with free parking nearby. It can comfortably accommodate 2 people, with an equipped kitchen, linen, soap and shampoo.