Vacation rentals in Val di Chiana

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Top-rated vacation rentals in Val di Chiana

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Guest favorite

Farm stay in Ruscello

4.99 out of 5 average rating, 323 reviews

Agriturismo Fattoria La Parita

Provençal-style apartment nestled between the vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. It includes a basic Italian breakfast (coffee, tea, milk, cookies, etc.) that you can prepare on your own, if you want to try one of the famous breakfasts prepared and served by Sandra, the cost is €10 per person (6€ 5 to 15 years)

Sep 1 – 8

G$33,119 GYD per night

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 109 reviews

Villa di Geggiano - Guesthouse

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Jan 11 – 18

G$104,251 GYD per night

Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 332 reviews

A view from the top

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2024 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Jan 19 – 26

G$33,482 GYD per night

Guest favorite

Vacation home in Cortona

4.95 out of 5 average rating, 203 reviews

La casina sulle Mura (with garden and spa jacuzzi)

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

Jan 15 – 22

G$23,106 GYD per night

Guest favorite

Home in Scrofiano

4.97 out of 5 average rating, 116 reviews

Jenny's Barn

The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

Oct 1 – 8

G$29,238 GYD per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 311 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Nov 30 – Dec 7

G$34,109 GYD per night

Guest favorite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 242 reviews

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Mar 29 – Apr 5

G$31,820 GYD per night

Guest favorite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 202 reviews

"Red Rose" apartment with a view of Siena.

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

Dec 30 – Jan 6

G$34,024 GYD per night

Guest favorite

Home in Monticchiello

4.97 out of 5 average rating, 135 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Nov 25 – Dec 2

G$67,190 GYD per night

Guest favorite

Villa in Ambra

4.98 out of 5 average rating, 108 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Villa with 5bedrooms and 10sleeps in Chianti . Land of wine, good food and old traditions. Distances from the villa to:Siena 25km,Arezzo 35km,Florence 60km,villa with swimming pool obtained from the careful restoration of an ancient stone farmhouse

Mar 27 – Apr 3

G$181,998 GYD per night

Guest favorite

Apartment in Monticchiello

4.99 out of 5 average rating, 299 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

Mar 13 – 20

G$52,644 GYD per night

Guest favorite

Farm stay in Pari

4.98 out of 5 average rating, 227 reviews

TUSCANY farm house SWIMMING POOL

Our little farm is a beautiful location for a relaxing vacation with a private swimming pool. We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

Apr 25 – May 2

G$20,766 GYD per night