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Holiday rentals in Filare

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Top-rated holiday rentals in Filare

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment
5 out of 5 average rating, 296 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home
4.96 out of 5 average rating, 107 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Superhost
The image captures a stone exterior of an apartment at sunset, with a large tree providing shade. Rays of golden sunlight filter through branches, illuminating a grassy area and distant hills. A paved stone path leads towards the entrance, enhancing the connection to nature.
Guest house
4.8 out of 5 average rating, 192 reviews

Appartment 1 surrounded by Tuscan Nature

This detached appartment has 55 mp with kitchen, bathroom, bedroom, and terrace. It is built in the traditional tuscan style with stone and wood. Its 20 minutes drive to the sea,1 hour to Siena, 2 hours to Rome and Florence, 5 minutes to Caldana city Center where you have all amenities (groceries, bank, Postoffice,3 restaurants..) You will find a lot of activities like horseriding,excursions of history and plants,winetasting and kilometers of wonderfull beaches, watch the birds and wild animals.

Top guest favourite
Flat
4.91 out of 5 average rating, 183 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 143 reviews

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.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 202 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay
4.99 out of 5 average rating, 265 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Guest favourite
A spacious terrace offers stunning views of the surrounding mountains and the charming town below. Potted plants line the edges, while a wooden dining table with matching chairs is positioned for outdoor dining. The soft sunlight enhances the inviting atmosphere of the space.
Flat
4.91 out of 5 average rating, 23 reviews

Casa Vacanze Enos & Iside

In the heart of the charming historic center of Ravi is Casa Enos&Iside, perfect for families looking for relaxation and tranquility. This spacious home is ideal for those who want to immerse themselves in the authentic atmosphere of an ancient village, while enjoying all the modern comforts. Strategically located, the house allows you to easily discover the wonders of the surrounding area, from medieval villages to green hills, from food and wine trails to pristine beaches

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 220 reviews

Sunset on Chianti Classico

If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

Top guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Flat
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Top guest favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Apartment
4.97 out of 5 average rating, 319 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 to 20 which is in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and Wi-Fi Strategic location for visiting Tuscany and Umbria.

Top guest favourite
A ceramic vase filled with vibrant yellow flowers is prominently displayed on a table. Soft light from a lamp illuminates the rustic stone wall in the background, enhancing the warm ambiance of the space. Two mugs sit beside the vase, adding a touch of comfort.
Flat
4.93 out of 5 average rating, 107 reviews

Leo's porch

Stay in this unique place and spend unforgettable evenings gazing at the horizon. Breathe clean air and enjoy the relaxation offered by the village of Scarlino. Ideal for couples or small families who want functional and comfortable accommodation. FROM MAY 1 TO AUGUST 31, a tourist tax of €1.00 per night/person is applied for each day of stay. Bed linen and towels are NOT INCLUDED in the final price of the accommodation.

Popular amenities for Filare holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Filare