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Holiday rentals in Cireglio

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Top-rated holiday rentals in Cireglio

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Top guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Apartment in Noce
5 out of 5 average rating, 191 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Top guest favourite
A rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.
Flat in Carmignano
4.97 out of 5 average rating, 261 reviews

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...

Top guest favourite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home in Vaiano
4.99 out of 5 average rating, 260 reviews

Tuscan cottages in an ancient villa with a garden

The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

Top guest favourite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home in Vaiano
5 out of 5 average rating, 261 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients, such as bio vegetables, eggs or cheese.

Top guest favourite
An outdoor dining area is illuminated softly by warm lights, surrounded by lush greenery and climbing roses. A stone patio features a table set for guests, with several chairs positioned nearby, creating an inviting space for al-fresco meals.
Cottage in Metato
4.96 out of 5 average rating, 107 reviews

Tuscan cottage, sea view and private olive garden

Metato26 is a unique, newly renovated residence blending traditional Tuscan soul with contemporary comfort. High-speed internet facilitates remote working in silence. Ideal for multigenerational privacy, we include a complimentary pasta class and local insight. Outside: a 200sqm garden with wisteria and rose pergolas, a jacuzzi, and a fenced 600sqm sea-view olive grove. Pet-friendly and authentic, moments from the Italian Riviera and the art cities of Tuscany. This is the real thing.

Top guest favourite
A lush garden surrounds the farmhouse, featuring a winding brick pathway lined with vibrant greenery and colorful flowers. Mature trees provide shade, and a variety of plants contribute to a serene atmosphere, enhancing the natural beauty of the outdoors.
Apartment in Strada In Chianti
4.95 out of 5 average rating, 397 reviews

Chianti Apartment in 12th Century Tuscan farmhouse

Your separate apartment in our secluded 12th century farmhouse has its own entrance and is on two levels; kitchen and sitting area is on the first floor, beds and bath are upstairs. The large fireplace in the kitchen is very typical in these old houses. In the sleeping rooms we have air conditioning. The garden is unique , a place to relax and enjoy. If there is no available date check out our second new listing, same property, "Chianti Patio Apartment" Pleased to welcome you!

Superhost
A cozy bedroom features a wrought-iron canopy bed with crisp white linens. Natural light enters through a window, flanked by a small potted plant. Exposed wooden beams adorn the ceiling, enhancing the rustic charm of the space.
Home in Pistoia
4.9 out of 5 average rating, 10 reviews

In Tuscany's Heart: big house w/view 1h from all

Let yourself be pampered by the sounds of nature in which this accommodation is immersed! Experience the relaxation of the countryside by staying in a spacious and cosy house immersed in the quiet of the Pistoia hills. Located in a semi-exclusive context, you will also be in a strategic position to visit much of Tuscany, less than an hour's drive from the main points of interest such as Florence, Pisa, Lucca, the beautiful Tuscan coast or the cool Pistoia mountains.

Top guest favourite
Castle in Tignano
5 out of 5 average rating, 14 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Guest favourite
An outdoor terrace is shown, featuring a large umbrella providing shade over a dining table. Two lounge chairs are positioned nearby on a tiled surface. Lush greenery lines the perimeter, with a small black table and potted plants adding charm.
Holiday home in Cireglio
4.93 out of 5 average rating, 40 reviews

Lovely home in the Tuscan hills

You will be the only guests of the property and this guarantees privacy and tranquility. My wife and I live in the remaining part of the cottage, and we will be the only discreet presence. You will have the opportunity to relax on the furnished terrace at your disposal, or on the hammock surrounded by greenery or in the Jacuzzi (available from June to September), all for your exclusive use. The entire garden of the villa can be used for walks and relaxation.

Top guest favourite
An outdoor patio is illuminated by string lights, enhancing the rustic stone walls of the house. A wooden dining table with chairs is set for gatherings, while the door leads to the interior living space. Lanterns are positioned on the ground, adding ambiance.
Home in Cireglio
5 out of 5 average rating, 33 reviews

M.SommerHouse Nature & Silence in Tuscany

Historic stone house in Castel di Cireglio, a small and charming medieval village in the heart of the Pistoia mountains, ideal for exploring Tuscany. Pistoia can be reached in just 15 minutes, Florence and Lucca in half an hour by car or train, Viareggio, Pisa, and Livorno in less than an hour, and Abetone in forty minutes. An authentic place, surrounded by woods, ideal for those seeking peace, tranquility, and contact with nature, far from mass tourism.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 457 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favourite
A sunlit terrace features a round table surrounded by four wrought-iron chairs. Lush greenery and vibrant flowers are visible in the background, along with a stone wall creating a rustic ambiance. An archway adorned with climbing plants provides a charming focal point.
Flat in Massa e Cozzile PT
4.95 out of 5 average rating, 188 reviews

Tuscan farmhouse cottage with terrace and views

Independent apartment on the property of a traditional Tuscan farmhouse, surrounded by olive groves, with a large terrace and spectacular views of medieval village and valley. The aparment is fully equipped and has its own independent entrance. Perfect location for visiting Florence, Lucca, Pisa, Siena and the sea. Walking distance to charming medieval village. Perfect for country walks and discovering Tuscan cuisine in local restaurants.

Popular amenities for Cireglio holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pistoia
  5. Cireglio