
Holiday rentals in Cupi
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Top-rated holiday rentals in Cupi
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Casa Allegra
Independent apartment on the ground floor of a farmhouse surrounded by nature, on the edge of the Maremma Regional Park and a few kilometers from the sea. Convenient location for discovering the Maremma, between Argentario and Punta Ala. It is possible to visit Rome, Florence, Siena and Pisa, which are well connected by train and bus.It consists of a living area with a kitchen and sofa bed, a double bedroom, and a bathroom with a window and shower. There is a large garden with a BBQ, table, and deck chairs for relaxing. Adjacent to the bike path (Magliano-Parco Maremma).
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Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
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Beach House Giannella w/ direct access to the sea
The villa is surrounded by a 1500 sq m garden with pines, Mediterranean plants and flowers, and includes a private sandy beach directly bordering the sea.It is composed of a living room, a kitchen, two double bedrooms, a bedroom with a bunk bed and two bathrooms (one of which in a small external structure). It is provided with air conditioning and a heat pump.In the park, there is an outdoor kitchen and a large table under a gazebo on the beach, which allows you to eat right in front of the sea.
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Casa Olivia: Comfort, Nature and Landscapes of Maremma
Placed in the Manciano countryside, in the intact landscape of South Tuscany, 20 min from the Saturnia Cascades, Casa Olivia is an apartment in a farmhouse in the center of an age-old olive grove. From the garden and the house you can enjoy an incredible view on the Maremma hills with the Argentario coast in the background. Uncontaminated nature, peace and a wide choice of excursions in the surrounding area between art, history, sea and traditions. 30 minutes from beaches and beautiful villages
LocationFamilyWifi

Villa Il Molinaccio with terrace and private beach
Spacious rustic villa with a terrace overlooking the sea and access via stairs to a small pebbly beach. Ample outdoor and indoor spaces with garden. It has sun beds, sun umbrella, table tennis and barbecue. Recently purchased kitchen and furniture. A 10-minute walk from the harbour and centre, offering privacy but accessibility to all amenities like beaches, windsurfing, diving, and boat hire. Private garage in front of the house on private road. Recently renovated. Vintage and maritime style.
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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.
FamilyValueLong stay

Captain's House | Monte Grosso, Elba
The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.
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Villa Marsiliana
Villa immersed in the enchanting landscape of the Maremma countryside, ideal for those looking to spend a relaxing vacation surrounded by nature. The villa, elegantly furnished, can accommodate up to 8 people, perfect for families or groups of friends. You can enjoy the beautiful 10x5 meter swimming pool, perfect for sipping a drink or reading a book. The location allows you to explore the stunning beaches of the Tyrrhenian coast and the charming medieval villages. Security deposit €300
LocationFamilyGetting around

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
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Bel Casale with sea view and the mediaeval village
In the Maremma countryside, private panoramic swimming pool, with a 360° !!! View of the Argentario, the island of Giglio and the medieval village. Spectacular sunsets to admire! The villa is on one floor, characterized by exposed wooden beams, verandas, handmade terracotta floors, elegant minimal furniture. It can accommodate up to 6 people. Park of 2 hectares of garden with olive grove and centuries-old oaks. Located 5 minutes from the beautiful village of Pereta.
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Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
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Podere la Pompa
Villa with three bedrooms with ensuite bathroom, large kitchen and living room. External loggia for outdoor dining and possibility of using the shared swimming pool. Piccola Pompa is located a short drive from Grosseto and less than 20 minutes from the beaches of Castiglione della Pescaia
LocationFamilyBeach
Popular amenities for Cupi holiday rentals
Other great holiday rentals in Cupi

Incredible Views & Pool in the Tuscan Hills
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Amazing Tuscan beachfront apartment
LocationFamilyQuiet

Apartment surrounded by greenery with a sea view
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Podere Belvedere Classic Tuscan Villa
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Assiolo
LocationFamilyAccess

Villa with pool in the middle of Maremma
LocationFamilyNearby

Sea, charm, and comfort in Tuscan Maremma
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‘IL PEPERONCINO’ TUSCAN VILLA WITH PRIVATE POOL
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Destinations to explore
- Elba
- Giglio Island
- Lake Bolsena
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Centro Storico Orvieto
- Cascate del Mulino
- Mount Amiata
- Terme Dei Papi
- CavallinoMatto
- Siena Cathedral
- Vulci
- Necropolis of Tarquinia
- Palazzo Pubblico
- Terme San Filippo
- Saturnia Thermal Park
- Rimigliano Natural Park





