Holiday houses in Castiglione della Pescaia

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, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Panoramic villa with a terrace overlooking the sea

Just an 8-minute walk from the sea, this 150-square-meter villa surrounded by greenery, located on the first floor, offers breathtaking views of the sea and the beach of Castiglione della Pescaia. Bright and spacious, it has 4 bedrooms, 3 bathrooms (2 with shower), a living room, an equipped kitchen, and a washing machine. The highlight is the panoramic terrace and the sea-view attic, perfect for relaxing at sunset. With free Wi-Fi and air conditioning, it is ideal for those looking for nature, comfort and relaxation in Maremma.

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

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.

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Casa Vista Sea and Maremma

Welcome to your peaceful oasis in Castiglione della Pescaia! Located in a quiet residential area, our house offers a magnificent view of the Maremma and is just a 15-minute walk from the historic center and a 5-minute drive from the beautiful beaches. Enjoy the perfect balance between relaxing in nature and seaside adventures, with the convenience of having all the attractions of the village at your fingertips. Your ideal getaway to discover the wonders of Tuscany awaits you.

Apartment da Iris

Apartment at the doorsteps of downtown and the seaside establishments of Castiglione della Pescaia. 15 minutes walking from the first beach, 5 minutes by bike! A few meters from the main supermarkets and the small shopping center with fish shop, pharmacy, laundry and basic necessities. It also offers a green area (condominium) and views of the hills. Everything is easy to reach on foot, by bike ( FREE upon request ) and car, with free parking on site.

La Dolce Vita Romantic Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families, and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay in the midst of nature.

Charming loft nestled in the medieval village

Charming apartment located in a 17th century building in the enchanting medieval village of Castiglione, a historic area overlooking the sea and protected by the ancient Aragonese walls. Living area characterized by an ancient brick arch and the combination of old and modern, where wood and stone dominate. Located just 600m (10min walk) from the beach and 100m from free parking lot.

Santa Agata "Terrazza", 6-8 people 9 km to the sea

Large living room Kitchen (gas stove, dishwasher) 2 bathrooms with shower and toilet (no bidet) Bedroom with three beds Bedroom with two beds Bedroom with two beds Bedroom with one bed Covered balcony with dining table Large open terrace Shared barbecue Garden seating area with lounge chairs Parking space Wi-Fi

Brand new apartment “Summer Wind”

Brand new apartment located in a cool and strategic area, where you can enjoy a relaxing vacation with every comfort. Looking out from the terrace you can admire the Diaccia Botrona Nature Reserve and the sea in the background. Beaches and downtown are easily reached on foot or by bike.