
Vacation rentals in Castiglione dei Pepoli
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Top-rated vacation rentals in Castiglione dei Pepoli
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Simona Comfort & Relax Apartment
🏡 Welcome to Simona Comfort & Relax Your home in the Apennines, between Bologna and Florence. ✨ STRENGTHS: 🔑 Self Check-in: Arrival in total freedom 24 hours a day. 🚗 A1 8 min away: "Badia" exit. Ideal stop between North and South in both directions. 🏥 Nobili Clinic: Just 2 minutes (10 minutes on foot), to stay close to your loved ones in a welcoming environment. 🌲 Apennines: Stop on the Via Lana e Seta and 5 km from the Suviana and Brasimone Lakes. 📍 Close to the center: Restaurants, bars and services just a few steps from the house.
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Apartment in Grizzana, Bologna Apennines
Just 8 km from the highway, Rioveggio exit, and 3 km from the train station, getting to Bologna or Florence takes about 1 hour. You will have a large apartment of 60 square meters with an independent entrance. The Monte Sole Park is a stone's throw away and nearby there are the Rocchetta Mattei and the Corno alle Scale mountains. The kitchen is complete with dishes and pots, a microwave and a coffee maker, with coffee, barley, chamomile and tea, some croissants, carbonated and natural water, and milk at your disposal.
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Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience
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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 and Mugello 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.
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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.
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House with a view surrounded by nature_ 5
A cozy stone and wood chalet with amazing views of the Apennines, surrounded by nature with a large garden where you can relax and enjoy the spectacular sunsets. We will be happy to host you on the ground floor which is dedicated to the B&B. The warm and welcoming rooms have independent entrances and lead onto the garden. Fantastic location between Bologna and Florence, 10' from the motorway exit and 30' from Bologna airport. Don't miss the sunset, even better with a good glass of wine!
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House nestled in the Apennines
The house is near the path of the gods and the wool and silk roads. The 120 sqm house, consisting of a kitchen with dining room, bathroom, dining room, laundry room, 2 double bedrooms (with 4-door wardrobe), single bedroom (with 4-door wardrobe), laundry room and garden. Immersed in the green of the Emilian Tuscan Apennines, about 45 km from Bologna and Florence, with a breathtaking landscape and perfect for those who want to walk and get away from the weariness of the city.
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Il Castello di 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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Ancient manor La Ploca
A charming studio apartment, perfect for couples looking for romance, solo travelers, or anyone who wants to break away from the routine and rediscover the beauty of nature and history. Nature, History and Relaxation in the Tuscan-Emilian Apennines. Experience the unique experience of staying in an authentic 14th-century manor, which belonged to the ancient family of the Counts Pepoli, immersed in a large park in Castiglione dei Pepoli, between Bologna and Florence.
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Cozy hilltop retreat w/ midcentury decor fully AC
Perched on top of a hill in the countryside between Bologna and Modena, this lodge is a great location for exploring the area. It's a peaceful place, with panoramic views and the convenience of having excellent local restaurants (& wine makers) nearby. The house, decorated with mid century design & furniture and fully air conditioned, has 4 sleeping rooms and 5 bathrooms. Please note: you need a car to reach us and to enjoy the area. Thank you for reading this!
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[Overlooking the hills] Green Hill Maranello
Style, light, silence and a breathtaking view of the hills. An exceptional flat just 10min from Maranello. The house, completely renovated and furnished with taste and attention, consists of: -Large living area with living room with sofa bed and fully equipped kitchen - Large panoramic terrace - Two elegant double bedrooms - Bathroom with shower Powerful wifi and private parking. An oasis of relaxation and nature, 10min drive from all city services!
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[SAN LORENZO-DUOMO] Prestigious Historic Residence
Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.
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Popular amenities for Castiglione dei Pepoli vacation rentals
Other great vacation rentals in Castiglione dei Pepoli

Church of the Vaioni
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Bright house with garden and mountain views
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Penthouse in small medieval castle near Florence
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Futa Pass - third stage - The Way of the Gods
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RelaisMor Villa with park in the Tuscan-Emilian Apennines
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I Palpiti - Dream Villa in the heart of Florence
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Rural Tuscany | Panoramic resort with tennis court
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The Balcony
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Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Bologna Center Town
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Bologna Fiere
- Mugello Circuit
- Stadio Renato Dall'Ara
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Mercato Centrale
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Appennino Tosco-emiliano National Park
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazza Maggiore
- Autodromo Enzo e Dino Ferrari
- Piazzale Michelangelo
- Piazza della Signoria





