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Holiday rentals in Castell'In Villa

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Top-rated holiday rentals in Castell'In Villa

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Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat
4.97 out of 5 average rating, 131 reviews

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top guest favourite
The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.
Flat
4.99 out of 5 average rating, 164 reviews

Villa di Geggiano – Alfieri Suite

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.

Top guest favourite
Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.
Flat
4.94 out of 5 average rating, 141 reviews

Loggiato 2 Apartment in Tuscany with pool

The Loggiato 2 apartment for 2 people is located in the Santa Lucia farmhouse (THE FARMHOUSE IS DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is a two-room apartment located on the first floor with a private table in front of the windows of the entrance loggia. There is a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen and television. The apartment has air conditioning in the room (for a fee).

Top guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage
5 out of 5 average rating, 103 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Guest favourite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home
4.91 out of 5 average rating, 111 reviews

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Top guest favourite
The charming stone facade of the historic building is complemented by large green shutters and terracotta pots filled with vibrant plants. Sunlight illuminates the outdoor area, highlighting the welcoming entrance surrounded by steps and a spacious patio.
Flat
4.93 out of 5 average rating, 227 reviews

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).

Guest favourite
A spacious garden is featured, showcasing manicured green grass and pathways lined with stones. A shaded seating area is positioned beneath a gazebo, with metal chairs inviting relaxation. Lush hedges and a view of distant vineyards complete the scene, offering a serene outdoor atmosphere.
Home
4.9 out of 5 average rating, 132 reviews

Casa Nataly Chianti – Jeky Stay

Typical Tuscan apartment in the wonderful village of Villa a Sesta, immersed in the tranquility of the Chianti hills. Part of Jeky Stay. A strategic point for bike rides, tastings in local wineries and visits to villages such as Pienza, Siena, San Gimignano, Montalcino and Florence. Rapolano's thermal baths are also just a few kilometres away. Enjoy typical dishes and local wines in the village trattorias

Top guest favourite
A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.
Loft
4.95 out of 5 average rating, 245 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Top guest favourite
A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.
Flat
4.98 out of 5 average rating, 107 reviews

Casa Guardiavigna in Chianti, Italy

The Casa Guardiavigna apartment offers the opportunity to enjoy a unique and extraordinary experience, full of emotions and happiness. Located a stone's throw from the small medieval village of San Gusme' and surrounded by beautiful vineyards, woods and flowery meadows. Free indoor parking with an automatic gate.

Top guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay
4.96 out of 5 average rating, 103 reviews

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Top guest favourite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home
4.97 out of 5 average rating, 192 reviews

Secret Garden Siena

A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Top guest favourite
A spacious bedroom features a large bed with a patterned coverlet. Two open doors lead to a private balcony with a table and chairs. Natural light floods the room, highlighting the scenic view of the surrounding hills and trees.
Home
4.98 out of 5 average rating, 455 reviews

Raffaella's House in Chianti

Rent apartment with great view in the hills of Chianti, with air conditioning, wifi, sat tv, garage for motorcycles and bicycles and private parking. Breakfast in a beautiful veranda. Will welcome you the friendly Raffaella.

Popular amenities for Castell'In Villa holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Castell'In Villa