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Holiday rentals in Chianciano

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Top-rated holiday rentals in Chianciano

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious bedroom features a large bed with beige striped bedding and decorative blue cushions. A vibrant blue accent wall is complemented by a piece of wall art. Natural light enters through large windows adorned with roller shades, revealing views of the surrounding countryside.
Apartment in Stabbiano
5.0 out of 5 average rating, 84 reviews

Gli Ulivi Apartment & SPA

Gli Ulivi Apartment & SPA is a modern accommodation with attention to the smallest details, equipped with all amenities and a small private SPA. Located in S. Albino di Montepulciano in a panoramic position, surrounded by the green hills between Valdichiana and Val d'Orcia. The entire apartment consists of two large double bedrooms, an open space consisting of a large living room with fireplace and kitchen. Private spa with sauna and two-seater whirlpool tub, two bathrooms with showers and a large balcony.

Top guest favourite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Holiday home in Chianciano Terme
5.0 out of 5 average rating, 128 reviews

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Top guest favourite
Villa in Montepulciano
4.97 out of 5 average rating, 125 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

Top guest favourite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme
4.97 out of 5 average rating, 128 reviews

Charming TuscanVilla with View for Family&Friends

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 246 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

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 in Montepulciano
4.98 out of 5 average rating, 163 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 or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 332 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Guest favourite
A spacious sleeping area is characterized by high wooden beams and light-colored stone floors. A large bed is positioned centrally, accompanied by two bedside lamps. Natural light fills the room through multiple windows, framed by elegant shutters. A simple desk and chair are also present.
Flat in Chianciano Terme
4.83 out of 5 average rating, 88 reviews

collitorti | Guest House Original Design

Collitorti like the hills surrounding our humble home located on the ridge dividing the Valdichiana from Valdorcia. Located in the open countryside, at the foot of the historic town of the thermal town, the apartment is part of the ancient farm Cerettellini. Decorated with care and simplicity, it consists of a large living room with a comfortable sofa bed, kitchen and double bedroom with bathroom, which open onto the panoramic garden belonging to the apartment. It has wifi and tv.

Guest favourite
An outdoor patio area features a covered gazebo with six black chairs and a small table. The entrance door is framed by a stone wall, surrounded by lush greenery, creating a calm and inviting space for relaxation.
Flat in Chianciano Terme
4.94 out of 5 average rating, 66 reviews

La Casa di Ambra Nature and Relaxation

La Casa di Ambra is located in an excellent position at the center of every need. The house can comfortably accommodate 4 people. It has a living room with a fireplace and a comfortable sofa bed for a possible fifth guest, a large equipped kitchen, 2 double bedrooms, a bathroom with shower, a veranda with washing machine, a patio with a furnished gazebo, a small garden and parking for 2 cars right in front of the house entrance. The house has been recently refurbished.

Top guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano
4.97 out of 5 average rating, 158 reviews

Stone farmhouse in Val D'Orcia

19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

Top guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello
4.96 out of 5 average rating, 137 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Superhost
A spacious terrace is covered by a large canopy, providing shade over several outdoor seating options. Two chairs in a relaxing position are positioned alongside a glass table, with a background of greenery and a neighboring building visible.
Home in Chianciano Terme
4.82 out of 5 average rating, 11 reviews

House Dreams Toscany

🏡 Modern apartment with a large panoramic terrace in the heart of Tuscany 🌿 Discover the pleasure of staying in this elegant apartment located in a quiet area of Tuscany, perfect for families or groups of friends. The apartment has air conditioning, free Wi-Fi and a flat-screen TV. The location is ideal for exploring the villages, vineyards and hills of Tuscany, while remaining just minutes from the main services.

Popular amenities for Chianciano holiday rentals