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Holiday houses in San Benedetto in Alpe

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Top-rated holiday rentals in San Benedetto in Alpe

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Superhost
Villa in Poppi
5 out of 5 average rating, 4 reviews

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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Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 110 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

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Guest favourite
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

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Top Guest favourite
Villa in Bertinoro
4.98 out of 5 average rating, 81 reviews

LUXURY VILLA BELVEDERE - Sea View with Pool & Spa

Providing a truly authentic italian experience, the spacious and gorgeously decorated Villa Belvedere is magnificently set in a unique corner of the ancient village of Bertinoro, with breathtaking views of the peaceful and pictoresque Romagna hills, sea and coastline. Infinity pool heated upon request, hot tub, sauna, steambath, professional gym; cinema room, billiard, bar corner with wine cellar, fully furnished and carefully designed and maintaned garden with barbecue and outdoor games.

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Guest favourite
An outdoor terrace features a wooden roof supported by pillars, offering a view of lush green mountains and vibrant trees. A sun lounger is positioned on the stone flooring, which complements the natural setting. The clear blue sky enhances the tranquil atmosphere.
Barn in San Godenzo
4.95 out of 5 average rating, 19 reviews

Agriturismo La Castellina, Il fienile - San Godenzo

Welcome to the La Castellina agriturismo, a peaceful retreat in the hamlet of Castagno d'Andrea, in the municipality of San Godenzo. Located at the foot of the Foreste Casentinesi, Monte Falterona and Campigna National Park, Il Fienile combines comfort and tranquility. It offers 4 beds, a fully equipped kitchen and a large outdoor garden with pergola and furniture. Ideal for excursions, the main paths of the Upper Mugello and CAI trails start from here. Perfect for adventures or relaxation.

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Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 228 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

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Top Guest favourite
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

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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Guest favourite
Castle in Tignano
5 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

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Top Guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

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Top Guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 137 reviews

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

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Guest favourite
Apartment in Premilcuore
4.93 out of 5 average rating, 15 reviews

House on the screaming caves Ponte Nuovo Premilcuore

Appartamento sito sopra le Grotte Urlanti della suggestiva località Giumella - Premilcuore , un luogo immerso nella natura del Parco delle Foreste Casentinesi. Gualchiera del 1500/1600 di ristrutturazione del 2025 Ottimo punto di partenza per trekking, info in loco Possibilità di luogo chiuso e sicuro per le vostre biciclette. Per bimbi piccoli è a disposizione un lettino da campeggio con sponde alte. Parcheggio a circa 300 mt dalla struttura

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Superhost
Holiday home in Reggello
4.88 out of 5 average rating, 219 reviews

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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