
Holiday houses in Pieve Santo Stefano
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Top-rated holiday rentals in Pieve Santo Stefano
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Poggelleri the postcard on Poppi and Tuscan hills
Imagine waking up with the golden light of Tuscany filtering through the windows, the intoxicating scent of the countryside and the feeling of absolute peace. This villa awaits you for an unforgettable experience. Located in an exclusive and private location, it offers breathtaking views of rolling hills within walking distance of the most beautiful cities of art. If you are looking for a refuge where time seems to stand still, where beauty is everywhere and exclusivity is the watchword, you have found your ideal destination.
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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.
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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.
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The Balsaccia
Nestled in the green Tuscan countryside, between the hermitage of Cerbaiolo and the Piccolo Museo del Diario, and just a few minutes from the sites of Piero Della Francesca, a brand-new, modern and cosy cottage with spacious indoor and outdoor areas to enjoy the greenery and tranquillity. The apartment features an open plan space with a double bed, an armchair, a dining table and a kitchen with an induction hob, an electric kettle and a refrigerator. Room with a wardrobe, bunk bed and bathroom.
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Piazza Grande Boutique Apartment
Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.
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Cozy apartment in stunning National Park forest
This cosy apartment immersed in one of Italy's largest National Parks offers a breath of fresh air. Perfect for hikers - many paths begin direct from the door, ideal for those walking to La Verna. Just a 5min minute walk away are waterfalls and natural pools. In a unique area of the Casentino the tranquil village of Rimbocchi invites you to escape the chaos of urban life. Although remote, it's also a convenient base to visit many historic cultural towns all within an hour by car.
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The Castle of Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.
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[Bridgerton atmosphere] Historic residence in the village
Welcome to my beautiful new home in Sansepolcro! It has just been completely renovated and is as fresh as a daisy, but with a touch of Bridgerton style, making it historic, themed and classic 😃 🌿 An oasis of natural coolness: Located in a historic building in the centre of Sansepolcro, the apartment boasts thick original stone walls. This traditional insulation keeps the house beautifully cool and pleasant (around 24°C) even on the hottest summer days.
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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
LocationValueShared spaces

Experience rustic off-grid life in the wilderness
This ancient rustic farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves, the bumpy road and the lack of phone signal offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.
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Glamping Pandaland - Sisley
This cozy 18-square-meter wooden mini house offers a perfect retreat for those seeking relaxation and simplicity. Inside you will find everything you need for a comfortable stay: bed, equipped kitchenette and private bathroom. Outside, surrounded by trees, a heated hot tub, ideal for relaxing under the stars or after a day outdoors. A peaceful corner where you can rediscover silence and contact with nature, without sacrificing essential comforts.
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Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.
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Popular amenities for Pieve Santo Stefano holiday rentals
Other great holiday rentals in Pieve Santo Stefano

Barn
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Tuscan Villa with Private Jacuzzi & River
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Hidden gem in Tuscany
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Casa San Ripa: Relax Oasis with Private Pool
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Little Corticellitta in Tuscany
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Villa Cerfoglio, peace in the Romagna hills
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Grazioso Apartment
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Casa Ciappi
LocationFamilyLong stay
Destinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Pinarella Di Cervia
- Ponte Vecchio
- Mirabilandia
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fiera Di Rimini
- Misano World Circuit
- Stazione Santa Maria Novella
- Mercato Centrale
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Autodromo Enzo e Dino Ferrari
- Piazzale Michelangelo
- Basilica of St Francis
- Piazza della Signoria
- Palazzo Vecchio





