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Holiday rentals in Caldana

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Top-rated holiday rentals in Caldana

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

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 194 reviews

Casa al Gianni - The Simignano Barn

Converted from an old 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dinners. A memorable getaway awaits you in this little slice of paradise!

Top guest favourite
Apartment in Valpiana
4.98 out of 5 average rating, 47 reviews

Infinity Pool in the green agritourism with a view of the woods

Experience the authentic Tuscany between the sea and the countryside! Our Casetta Valmora estate is located 10 km from Follonica and Massa Marittima. The apartment with private patio, Wi-Fi, air conditioning overlooks the garden with two sun loungers, ideal for couples, families and friends. From June 2026, the new panoramic infinity pool with a view of the forest will be available for moments of pure relaxation. Nearby, discover medieval villages, Cala Violina, bike trails, golf (15 km away) and local products.

Guest favourite
Villa in Ribolla
5.0 out of 5 average rating, 6 reviews

Podere Raspollino | Maremma 10 people

Podere Raspollino is a Maremma farmhouse with two floors. On the ground floor there are two bedrooms and two bathrooms with a separate entrance! On the loggia overlooking the pool, you can find a barbecue and a fully equipped kitchen (without an oven)! Dining table and armchairs! On the first floor, there are three bedrooms and three bathrooms, a living room and a fully equipped kitchen! The farmhouse is located between Ribolla and Montemassi! About 55 minutes from Siena The nearest airport is Pisa

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Flat in Caldana
4.8 out of 5 average rating, 5 reviews

Apartment in the center of Caldana

In the charming medieval village of Caldana, just a short walk from supermarkets, bars, restaurants, and small local shops, this welcoming holiday apartment offers the perfect setting for a relaxing stay in Tuscany. The apartment features two cozy bedrooms, a spacious living and dining area, and a small separate sitting corner ideal for reading or unwinding. A true highlight is the large terrace with beautiful views. Centrally located this property combines comfort and authentic Tuscan charm.

Guest house in Caldana
4.79 out of 5 average rating, 199 reviews

Appartment 1 surrounded by Tuscan Nature

This detached appartment has 55 mp with kitchen, bathroom, bedroom, and terrace. It is built in the traditional tuscan style with stone and wood. Its 20 minutes drive to the sea,1 hour to Siena, 2 hours to Rome and Florence, 5 minutes to Caldana city Center where you have all amenities (groceries, bank, Postoffice,3 restaurants..) You will find a lot of activities like horseriding,excursions of history and plants,winetasting and kilometers of wonderfull beaches, watch the birds and wild animals.

Top guest favourite
A spacious terrace offers stunning views of the surrounding mountains and the charming town below. Potted plants line the edges, while a wooden dining table with matching chairs is positioned for outdoor dining. The soft sunlight enhances the inviting atmosphere of the space.
Flat in Ravi
4.95 out of 5 average rating, 37 reviews

Casa Vacanze Enos & Iside

In the heart of the charming historic center of Ravi is Casa Enos&Iside, perfect for families looking for relaxation and tranquility. This spacious home is ideal for those who want to immerse themselves in the authentic atmosphere of an ancient village, while enjoying all modern comforts. Located in a strategic position, the house allows you to easily discover the wonders of the surrounding area, from medieval villages to green hills, from food and wine routes to pristine beaches

Top guest favourite
Home in Massa Marittima
5.0 out of 5 average rating, 74 reviews

Design loft with private SPA in Tuscany

Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

Guest favourite
A sweeping view of rolling hills and lush greenery stretches across the landscape, with the ancient village of Caldana perched on a distant hilltop. The sky is filled with scattered clouds, creating a soft and natural light over the scene.
Flat in Caldana
4.94 out of 5 average rating, 66 reviews

Casa Grace: relax and smart working in Maremma

Available all year. The apartment is suitable for short and long stays, both for relaxing and business holidays (smart working). It's located in Caldana, an antique medieval village in the province of Grosseto, that is only 25-30 minutes from seaside locations such as Follonica, Castiglione della Pescaia, Punta Ala, and Cala Violina (considered one of the most beautiful beaches). Welcome gift upon arrival! SMALL PETS ARE WELCOME!

Guest favourite
A charming stone house from the 19th century is featured, surrounded by lush greenery and decorative potted plants. The entrance showcases a welcoming wooden door under a tiled awning, with a gravel path leading to the structure, enhancing the rural character of the landscape.
Home in Gavorrano
4.91 out of 5 average rating, 22 reviews

Podere La Fornace is a small Ferienparadies

On a 1.5 ha plot surrounded by 300 olive trees is this completely restored picturesque, beautiful natural stone house from the 19th century. A large garden with palm trees and secular trees and a 10x5 m pool guarantee a relaxing vacation. The main house is divided into 3 apartments, all with separate entrance, private garden area and cozy outdoor seating. Not far from it are 2 charming, single houses equipped with all comforts.

Top guest favourite
A two-story villa with a stone facade is set within a lush green garden. An outdoor hot tub is positioned on a tiled patio, complemented by terracotta planters. A wooden dining area is visible beneath a shaded porch, surrounded by trees and a low fence.
Villa in Basse di Caldana
4.98 out of 5 average rating, 53 reviews

Private villa in Maremma 15 minutes from the sea

Villa La Quercia - Garden&Relax offers a charming rustic retreat for your summer holidays – the perfect place to immerse yourself in the authentic beauty of the Tuscan Maremma, whether you’re looking for a romantic getaway for two or a family holiday. Villa La Quercia welcomes you with its traditional charm, characterised by stone walls, exposed wooden beams and charming furnishings that reflect the true rustic Tuscan style.

Top guest favourite
Apartment in Tirli
5.0 out of 5 average rating, 31 reviews

Spacious Flat just 15 Minutes from the Sea

Discover the perfect combination of modern Scandinavian comfort and Tuscan charm in this private flat located in the village of Tirli. The flat offers modern yet cosy interiors, two bathrooms, a fully equipped kitchen, two bedrooms and a balcony with all the amenities you need for a relaxing holiday away from the stress of everyday life.

Guest favourite
The villa's exterior showcases a charming Mediterranean-style design, featuring a terracotta roof and soft pink walls. The surrounding well-maintained lawn is bordered by tall trees, providing a serene backdrop, while outdoor seating is positioned on the patio, inviting relaxation.
Villa in Grosseto
5.0 out of 5 average rating, 27 reviews

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

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