Holiday houses in Castel San Gimignano

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Top-rated holiday rentals in Castel San Gimignano

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Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 164 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

2–9 Nov

$891 NZD per night

Guest favourite

Holiday home in Poggibonsi

4.94 out of 5 average rating, 108 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

18–25 Feb

$195 NZD per night

Guest favourite

Apartment in San Gimignano

4.97 out of 5 average rating, 168 reviews

Casa Irene

Casa Irene is a delightful Tuscan-style apartment, located on the second and top floor of a building just a 5-minute walk from the centre, 50 metres to Porta San Matteo and another 50 metres to Via Francigena. Due to the slippery position you can easily reach by car to park in the immediate free parking lot. The apartment with wifi and air conditioning is divided into open space living room/kitchen,bedroom and bathroom with shower and a living terrace overlooking the walls of San Gimignano

3–10 Feb

$168 NZD per night

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 108 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.

9–16 Nov

$935 NZD per night

Guest favourite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 308 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.

30 Nov – 7 Dec

$269 NZD per night

Guest favourite

Tower in Fiesole

4.95 out of 5 average rating, 153 reviews

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.

23–30 Aug

$1,527 NZD per night

Superhost

Farm stay in Simignano

4.82 out of 5 average rating, 106 reviews

Casa al Gianni - Hut

Hi, we are Cristina & Carmelo! We invite you to live an authentic experience in our farm "Casa al Gianni" located 20 min from Siena. Our brand is the simple life in close contact with nature and the animals of our farm. Surrounded by woods and the beautiful Tuscan countryside, you will spend an unforgettable holiday. This corner of paradise will stay in your heart!

3–10 Feb

$157 NZD per night

Guest favourite

Home in Poggibonsi

4.9 out of 5 average rating, 215 reviews

Tuscan Counrtry Detached House. Wi-Fi Free

Do you want to spend your holiday in a typical Tuscan barn? This is your place! Charming renovated barn for families / groups. Located in the heart of the Tuscan countryside at 2km from Poggibonsi. Ideal for a relaxing holiday and in a great location for visiting San Gimignano (13km), Siena (25km), Florence (35km).

22–29 Mar

$170 NZD per night

Guest favourite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 200 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with panoramic views of Siena. Located at the Villas of 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..).

4–11 Jan

$255 NZD per night

Guest favourite

Cottage in Volterra

4.9 out of 5 average rating, 162 reviews

Podere Grignano, beautiful Tuscany

If the calendar indicates no availability, please check our other advert through the Airbnb map (Podere Grignano, beautiful Tuscany with a dot at the end). The other house can still be free. The houses are semidetached, The 2 houses are practically identical. The reviews are of both houses.

29 Jan – 5 Feb

$153 NZD per night

Guest favourite

Condo in San Gimignano

4.95 out of 5 average rating, 110 reviews

Adalberto Apartment inside the Manor of Fulignano

In the countryside of San Gimignano, in an ancient fortification dating back to the year 1000 hour country house, located on a hill with panoramic views, for rent a beautiful apartment of approx. 60sqm with views of San Gimignano and the surrounding vineyards

22–29 Oct

$186 NZD per night

Guest favourite

Apartment in Monticchiello

4.99 out of 5 average rating, 297 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 ...

25 Feb – 4 Mar

$434 NZD per night