Vacation rentals in Pergognano

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Top-rated vacation rentals in Pergognano

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Top guest favorite

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 in Ruscello

4.99 out of 5 average rating, 439 reviews

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. A basic Italian breakfast (coffee, tea, milk, biscuits, etc.) is included, but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 for 5 to 15 years, free for children under 5 years). EV wallbox available.

Top guest favorite

A charming exterior view of the accommodation is presented, featuring a white building with wooden windows and a bell tower. Lush greenery and terracotta pots filled with plants adorn the garden area, while an outdoor table with an umbrella offers a shaded seating option.

Apartment in Castiglion Fiorentino

4.98 out of 5 average rating, 57 reviews

"Borgo Sant'Andrea al Pozzo" in Ancient Abbey

Completely renovated residence within an ancient Abbey, already mentioned in 1114 A.D. and owned by the Camaldolese friars in the 12th century. A few meters from the historic walls of Castiglion Fiorentino dating back to 1200 AD and Porta Romana. It is a 500-meter walk from the historic center of Castiglion Fiorentino and a 15-minute drive from Cortona. A unique stay, between history and nature, in a relaxing and reserved setting. Strategic point for visiting Siena, Pienza, Anghiari, Arezzo, Cortona...

Top guest favorite

A cozy window nook is shown with a domesticated cat sitting beside a potted plant filled with pink flowers. A glass of sparkling water rests nearby, and a book is placed on the wooden surface, creating an inviting atmosphere.

Condo in Castiglion Fiorentino

5 out of 5 average rating, 17 reviews

Casa Letizia apartment in the historic center

Delightful apartment in a medieval historic building, in the historic center of Castiglion Fiorentino, a stone's throw from the Cassero tower and the Vasari Loggia, on Corso Italia. Close to a wine shop, pizzeria, shops, restaurants, clubs and bars located in the center, next to services (bank, post office, offices). Just a 2-minute walk to the parking lot right outside the walls. Close to the train station (about 800 meters) Close to bus station (about 150 meters). Free public parking 50 m away.

Top guest favorite

A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.

Apartment in Cortona

4.99 out of 5 average rating, 162 reviews

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

Top guest favorite

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.

Guesthouse in Macciano

4.97 out of 5 average rating, 179 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.

Guest favorite

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Villa in Castiglion Fiorentino

4.91 out of 5 average rating, 216 reviews

Tuscan charm of villa - countryside

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

Top guest favorite

An aerial view of the villa is displayed, surrounded by lush greenery and tall trees. The structured layout includes a main building with a red-tiled roof and several smaller buildings. A clear swimming pool can be seen adjacent to the main structure, enhancing the serene landscape.

Villa in Arezzo

4.93 out of 5 average rating, 15 reviews

Casa Napoleone - Tuscan Villa w/ pool near Cortona

A villa set on a hill, overlooking a magnificent Tuscan valley, yet only 10 mins drive from Castiglion Fiorentino train station. A 20 min drive from Arezzo and Cortona, a town made famous by the book and movie “Under The Tuscan Sun”. The Villa is the perfect base and within striking distance of Florence, Siena, Assisi and Montepulciano, famous for its Brunello wine, either by car or train. And after all that exploration you’ll return to soak in the pool whilst enjoying the stunning views.

Top guest favorite

An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.

Villa in Cortona

5 out of 5 average rating, 79 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Top guest favorite

A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.

Home in Anghiari

4.99 out of 5 average rating, 240 reviews

Casa Rosmarino Eco-Wellness Country Home

Price includes the WELLNESS & COMFORT package as follow: - Organic Wooden Fired Hot Tub w/Jacuzzi (1 water filling good for 4 days of use) - Infrared Sauna - Wood for Fireplace & Hot Tub - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Italian Ground Coffee - Treats during your stay Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Top guest favorite

A bright living space is featured, showcasing a wooden dining table set with dishes and fresh fruit. A comfortable sofa is positioned adjacent to the television on the wall. Natural light filters through a window, illuminating the wooden beams of the ceiling.

Condo in Cortona

4.98 out of 5 average rating, 179 reviews

Chicca: bright and panoramic in the historic center

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.

Top guest favorite

A stone exterior is showcased, with a staircase leading up to the entrance. A shaded area features outdoor seating, including a table and chairs. Potted plants line the pathway, and greenery provides a serene backdrop, enhancing the outdoor living space.

Home in Prato

4.99 out of 5 average rating, 125 reviews

Tofanello Turquoise Luxury with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Top guest favorite

The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.

Apartment in Cortona

4.97 out of 5 average rating, 376 reviews

Cortona Shabby Chic | Balcony• 10% off August dates

10% 🔥discount in August (22-24, 28-31). Cortona Shabby Chic with a private balcony and total privacy, perfect for relaxation. My place is located in the heart of the historic center just a few steps from the main squares and streets This lovely apartment has been recently renovated and can accommodate up to 3 people. Independent apartment with a single entrance, all on one floor. Furnished with care and equipped with all comforts