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Vacation rentals in Castiglione dei Pepoli

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Top-rated vacation rentals in Castiglione dei Pepoli

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

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Guest favorite
Townhouse in Scandicci
4.88 out of 5 average rating, 337 reviews

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

Top guest favorite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home in Vaiano
5 out of 5 average rating, 278 reviews

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.

Top guest favorite
Apartment in Castiglione dei Pepoli
4.97 out of 5 average rating, 180 reviews

Appartamento Simona Comfort & Relax

🏡 Benvenuti da Simona Comfort & Relax La tua casa nell'Appennino, tra Bologna e Firenze. ✨ PUNTI DI FORZA: 🔑 Self Check-in: Arrivo in totale libertà h24. 🚗 A1 a 8 min: Uscita "Badia". Tappa ideale tra Nord e Sud in entrambe le direzioni. 🏥 Clinica Nobili: A soli 2 min (10 min a piedi), per stare vicini ai propri cari in un ambiente accogliente. 🌲 Appennino: Tappa Via Lana e Seta e a 5km dai Laghi Suviana e Brasimone. 📍 Vicina al centro: Ristoranti, bar e servizi a pochi passi da casa.

Top guest favorite
A rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.
Apartment in Carmignano
4.97 out of 5 average rating, 296 reviews

Giglio Blu Loft di Charme+ Air Conditioning

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

Guest favorite
A bright hallway connects several rooms, featuring wooden doors that lead to inviting spaces. A white console table, adorned with a flower arrangement and books, adds a touch of decor. Natural light filters through a nearby window, enhancing the warm tones of the tiled floor.
Home in Castiglione dei Pepoli
4.91 out of 5 average rating, 338 reviews

Casa immersa nell'Appennino

La casa è vicino al cammino degli dei e alla vie della lana e della seta. La Casa di 120 mq, composta da Cucina con sala da pranzo, Bagno, Sala da pranzo, Locale Lavanderia, 2 Camere matrimoniali(con armadio a 4 ante), Camera da letto singola (Con armadio a 4 ante) locale lavanderia e giardino. Immersa nel verde dell'appenino tosco Emiliano, A circa 45Km da Bologna e da Firenze, con un paesaggio mozzafiato e perfetto per chi ha voglia di camminare e allontanarsi dal logorio della città.

Top guest favorite
A charming stone chalet is surrounded by colorful autumn foliage, featuring wooden shutters and a balcony that overlooks the landscape. The vibrant leaves contrast with the earthy tones of the building, while the lush green lawn is scattered with fallen leaves.
Cabin in Monzuno
4.97 out of 5 average rating, 119 reviews

Casa con vista immersa nella natura_ 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!

Top guest favorite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home in Vaiano
4.99 out of 5 average rating, 287 reviews

Cottage in Toscana in antica Villa con giardino

Il Cottage è parte di una proprietà della famiglia Bernocchi, già presente nelle mappe della zona del 1500 ed e' situata proprio su di una antica via Romana che attraversava i monti della Calvana. Distante circa 9 km da Prato e 20 da Firenze. Il Cottage, liberi su tre lati, e' situato in posizione panoramica circondato da un parco privato, ideale per camminate e sport. Una vera e propria casa, con cucina, salotto, camera e bagno. Ampi spazi esterni, giardino e orto botanico.

Top guest favorite
A landscape view reveals rolling hills in autumn hues, with vibrant foliage in shades of orange and gold. In the distance, a church steeple rises against a backdrop of mountains under a soft, cloudy sky, suggesting a serene and picturesque rural setting.
Apartment in Monzuno
4.96 out of 5 average rating, 279 reviews

Gorgeous One Bed Villa Overseeing the Apennines

Charming one-bedroom in Italian villa with a private terrace and brand-new air conditioning! Just a short walk from the famous Via degli Dei trail, this cozy retreat features a fully equipped kitchen, private bathroom, queen bed and breathtaking mountain views from your bedroom window. The friendly family below grows fruit and nuts and makes cakes, sauces and fresh pasta from scratch. Enjoy authentic countryside living with modern comfort and a warm, welcoming atmosphere!

Top guest favorite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 224 reviews

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.

Top guest favorite
The exterior of the lodge features vibrant green chairs and a round red table set on a grassy area. A spacious terrace is visible, surrounded by trees and offering views of rolling hills. Brightly colored windows add character to the building.
Condo in Monte San Pietro
4.99 out of 5 average rating, 489 reviews

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!

Guest favorite
An inviting terrace is presented with a dining set, featuring a table adorned with candles and glasses. Soft lighting highlights the space against a backdrop of rolling hills under a twilight sky, while plants and decorative stones frame the area.
Vacation home in Montagnana
4.94 out of 5 average rating, 158 reviews

[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!

Superhost
An outdoor space featuring a private pool surrounded by lush greenery. Lounge chairs are positioned along the poolside, and a gazebo provides shaded seating. The garden is well-maintained with colorful plants and a grassy area, creating an inviting environment for relaxation.
Villa in Castel di Casio
4.86 out of 5 average rating, 100 reviews

RelaisMor Villa con parco Appennino tosco emiliano

Porta tutta la famiglia e i tuoi amici in questo fantastico alloggio con tanto spazio per divertirsi e rilassarsi immersi nella natura. Ampio giardino e pineta a due passi dal lago di Suviana, dalla Rocchetta Mattei, dalle Terme di PORRETTA e dal paese medioevale di Castel di Casio. A disposizione per pernottamenti ma anche per eventi. Possibilità di utilizzo di piscina durante il periodo estivo. Vasca idromassaggio a pagamento secondo l'utilizzo.

Popular amenities for Castiglione dei Pepoli vacation rentals