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Vacation rentals in Caldana

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Top-rated vacation rentals in Caldana

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

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Guest favorite
Home in Asciano
4.96 out of 5 average rating, 126 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
Apartment in Caminino
4.91 out of 5 average rating, 188 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favorite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 151 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favorite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 104 reviews

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.

Guest favorite
An exterior view captures a charming terrace area adorned with potted flowers. A small table and two chairs are shaded by a white umbrella, offering a cozy space for outdoor dining. Stairs lead up to the entrance, framed by textured stone walls.
Vacation home in Caldana
4.88 out of 5 average rating, 58 reviews

The House of Kosen Rufu Independent apartment

Rent a 40 sqm independent apartment in Caldana (GR), a few kilometers from the most beautiful villages and the most beautiful beaches of the Tuscan coast. The apartment is composed as follows: independent entrance with garden, on the ground floor living room with double sofa bed, kitchenette with gas stove and coffee maker, balcony with breathtaking view, on the second floor bedroom with large window, bathroom with shower. Everything you need for your stay is provided Have a great vacation

Top guest favorite
A cozy living area features a light-colored sofa adorned with decorative cushions. Wooden beams span the ceiling, while a modern chandelier casts soft light. The kitchen is visible in the background, complemented by rustic cabinetry and stylish seating.
Apartment in Ravi
5 out of 5 average rating, 14 reviews

Yes Cino

Apartment in the heart of Ravi! Experience the authenticity of the Tuscan Maremma by staying in a cozy and completely renovated apartment, located in the historic center of Ravi, a charming 16th-century medieval village. Within walking distance you will find typical restaurants, local shops and breathtaking views of the Gavorranese countryside. Perfect for those looking for tranquility, history and nature. Ideal for romantic weekends or for a regenerating break away from the crowds.

Top guest favorite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 129 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favorite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 41 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favorite
Farm stay in Simignano
4.92 out of 5 average rating, 259 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favorite
A narrow stone hallway is seen from a small balcony, showcasing the rustic architecture of the surrounding buildings. An archway is featured overhead, and decorative iron railings frame the view of the cobblestone street below, lined with planters and dappled in sunlight.
Condo in Caldana
4.94 out of 5 average rating, 32 reviews

La Casina nel Contrada

If you are passionate about Tuscan villages, you will love this charming place. The 'Casina nella Contrada' is located in the heart of Caldana, which is an medieval town in the province of Grosseto. From here, you can enjoy the view of the historical centre. The house is suitable for 2 people, both for short and long stays. It only takes 20/30 minutes to reach beach destinations, such as Follonica, Castiglione della Pescaia, Punta Ala and the beautiful Cala Violina.

Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5 out of 5 average rating, 143 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Guest favorite
A wooden terrace offers two reclining chairs facing a scenic view of distant mountains and lush greenery. The space is framed by surrounding foliage, creating a serene setting for relaxation amidst nature.
Cottage in Vetulonia
4.89 out of 5 average rating, 102 reviews

La Quercia Panoramic 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.

Popular amenities for Caldana vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Caldana