Holiday rentals in Castiglion Fiorentino

4.92 out of 5 average rating, 587 reviews

An aerial view captures a serene farmhouse surrounded by rolling hills. A curving dirt road leads to the home, bordered by tall cypress trees. Soft sunlight bathes the landscape, highlighting the lush greenery and distant mountains.

Farm stay

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

4.99 out of 5 average rating, 497 reviews

A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.

Farm stay

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

4.96 out of 5 average rating, 131 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.

A spacious kitchen-living area features exposed brick walls and wooden beams. Two designer armchairs sit beside a round wooden table, with natural light entering through open windows. A well-equipped kitchen is visible in the background, contributing to a welcoming atmosphere.

4.96 out of 5 average rating, 314 reviews

A view from the gate, Montepulciano.

The house(castoldi apartments site), renovated in 2019, close to the main street and the Square has AC, 2 double rooms (1 or 2 king ), 2 bathrooms ensuite with shower and a large kitchen-living room with 4 windows and a small terrace, overlooking the hills, wine cellar The apartment offers a spectacular view Available in season a nice garden 50 mt away where to have a wine tasting for all the guests of our 4 apartments or grilled meat always with paired wines. Private parking in our garden.

4.97 out of 5 average rating, 221 reviews

Guest house

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.

4.9 out of 5 average rating, 235 reviews

Tuscan charm of villa - countryside - Villa Senaia

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

A scenic view of a hilltop village, characterized by its historic buildings and lush greenery. The landscape features a blend of trees framing the village, with a prominent structure atop the hill surrounded by cypress trees, creating a peaceful and rustic atmosphere.

4.99 out of 5 average rating, 158 reviews

Casa Dolce Toscana | Panoramic Suite with a View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

4.92 out of 5 average rating, 302 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

4.99 out of 5 average rating, 209 reviews

A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.

Apartment

Chicca: Cortona's historic centre

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Superhost

A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.

4.91 out of 5 average rating, 278 reviews

I Tramonti di Eramo, central Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

An aerial view of a stone farmhouse is presented, surrounded by lush greenery. A private garden features various seating arrangements, including loungers and a dining area under a sunshade. A pathway leads to the entrance, emphasizing the rustic charm of the setting.

5 out of 5 average rating, 27 reviews

Pendici 15, small apartment

Cozy apartment inside a stone farmhouse where you can enjoy the atmosphere of the Tuscan countryside and at the same time the proximity to the historic center of Castiglion Fiorentino. Ideal for couples, families and travelers with four-legged friends, it is the ideal starting point to visit Tuscany. The accommodation combines the rustic charm of stone houses with modern comforts, offering a relaxing stay in a quiet and panoramic setting.

Superhost

Apartment

4.9 out of 5 average rating, 314 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Popular amenities for Castiglion Fiorentino holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Castiglion Fiorentino

4.92 out of 5 average rating, 26 reviews

18th-century farmhouse in Cortona, with garden and 4 bathrooms

A spacious outdoor dining area is shaded by a rustic pergola covered in greenery. A large table is surrounded by multiple chairs, with views of the rolling hills in the distance. Colorful flowers and foliage add natural charm to the setting.

5 out of 5 average rating, 12 reviews

UPSTAIRS CUP Beautiful villa with superb view

A charming country home is nestled among olive trees, with a sunlit terrace visible in the foreground. The rustic stone facade complements the natural surroundings, while a pathway leads to the entrance. The landscape showcases rolling hills in the distance under a partly cloudy sky.

4.86 out of 5 average rating, 36 reviews

[Residenza Colle Secco] Country villa

4.94 out of 5 average rating, 16 reviews

Villa La Foce

4.92 out of 5 average rating, 25 reviews

Exceptional view of the valley in the center

5 out of 5 average rating, 19 reviews

Breathtaking views: Historic House w/Terrace & BBQ

4.93 out of 5 average rating, 14 reviews

casa Sonia

An outdoor dining area features a large table set for four under a spacious umbrella. Two lounge chairs are positioned nearby, surrounded by stone pavers and potted plants. The charming facade of the villa can be seen in the background, enhancing the peaceful ambiance.