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Holiday home rentals in Grosseto

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Grosseto

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Superhost
A scenic view of the villa's exterior is captured, featuring a terracotta roof and lush greenery. The vibrant colors of blooming flowers are visible alongside a panoramic view of the sea and coastal town below, enhancing the natural beauty of the surroundings.
Holiday home
4.79 out of 5 average rating, 24 reviews

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.

Guest favourite
Holiday home
4.98 out of 5 average rating, 90 reviews

House on the harbor - Il Partito

In the heart of Porto Ercole, on the first floor of a historic building on the waterfront, this holiday home of approximately 70 square metres – fully renovated in 2026 – offers all the charm of the Argentario: a balcony overlooking the harbour with a picturesque view of the sea and the moored boats, a private garden for relaxing outdoors, and a central location just a short walk from bars, restaurants and shops. As the owner of the IDROBOAT dinghy rental, I will be happy to suggest the most beautiful beaches.

Guest favourite
Holiday home
4.96 out of 5 average rating, 71 reviews

Meria di Maria - Pink Villa on the Beach

You'll love this pet- and baby-friendly villa close to the public beach and the seaside resorts. Don't you think that the convenience of stepping out of the garden and already being on the beach, having everything you could possibly need in the house, and having a host who is always ready to respond and offer advice are the hallmarks of a perfect holiday? In an excellent location, with everything close at hand, you can even leave your car in the car park and enjoy some well-deserved relaxation!

Top guest favourite
A bright double bedroom is presented with a spacious bed featuring crisp white linens. Natural light floods the room through an open window, framing a view of the surrounding valley. Wooden beams add character to the ceiling, and bedside tables with lamps are positioned beside the bed.
Holiday home
4.92 out of 5 average rating, 206 reviews

Stuart Jasmine central, panoramic top location

This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Top guest favourite
A rustic stone house is set amidst lush greenery, featuring large windows that invite natural light. The structure includes a covered terrace adorned with climbing plants, providing an inviting outdoor space. The surrounding lawn is well-maintained, contributing to a peaceful rural setting.
Holiday home
5 out of 5 average rating, 35 reviews

Elegant farmhouse overlooking Pienza

Podere Fonte Bernardi is an authentic Tuscan country house. Surrounded by the nature of the Val d'Orcia, an ideal place to relax. Located a few km from the most beautiful places in Tuscany such as Pienza, the medieval village of Monticchiello, the thermal site of Bagno Vignoni and the homeland of Montepulciano wine. Perfect for taking long walks and discovering local wines and food. You will be able to enjoy the most beautiful sunset over Pienza in the silence of the most authentic nature.

Guest favourite
The living and dining area features exposed stone walls and wooden beams, enhancing the rustic charm. A spacious sofa sits adjacent to a wooden dining table, surrounded by four chairs. Natural light filters in through a window, illuminating the tiled flooring.
Holiday home
4.93 out of 5 average rating, 117 reviews

Design apartment in Massa Marittima, "slow city"

A great 65 m2 - 2 bedroom Apartment, entirely renovated in freestone and exposed beams, with design touch. In the upper, medieval part of Massa Marittima, Siena in miniature, with a superb Romanesque cathedral. Central but quiet area. Many restaurants and oeno-gastronomic specialties. Magnificent freshwater lake, Lago dell'Accesa, 10 minutes by car. Sea at 20 minutes. Siena at 1:15 a.m. Massa, "Citta slow", offers many other activities: museums, wine cellars, horse riding, Bike Park, MTB

Guest favourite
A simple bedroom is presented with a spacious bed, featuring decorative pillows in warm tones. A mirror reflects a clothing rack and a framed photograph adorns the wall. Natural light enters through a window, enhancing the neutral color palette.
Holiday home
4.93 out of 5 average rating, 42 reviews

Casa Monteme, modern loft with views of the Maremma

Casa Montemè is located in the hills of Maremma, just a short walk from the Terme di Saturnia, in the ancient medieval village of Montemerano. Natural materials, traditional techniques, local craftsmanship and some contemporary touches have transformed an old traditional house into the vacation home of your dreams. Its location makes it ideal for those looking for a little relaxation and want to enjoy the wonderful villages of Tuscany! Kick back and relax in this calm, stylish space.

Top guest favourite
The exterior of a historical building is showcased, featuring a light-colored façade with traditional green shutters on each window. Archways at the ground level provide access, while the surrounding street reveals a mix of old-world charm and modern elements.
Holiday home
4.9 out of 5 average rating, 42 reviews

Palazzo Palloni: Main Floor

"Piano Nobile," nestled in the heart of the medieval town of Sorano, boasts 150 square meters of elegant living space, blending modern design with historic charm. As you step in, you'll find a spacious living room that flows into an open-plan kitchen, perfect for gathering with friends and family. With three bedrooms and two baths, it comfortably accommodates six guests. High-quality materials and designer lighting, all adds up to an unforgettable experience in the heart of Tuscany.

Superhost
A rustic stone farmhouse is gently illuminated at dusk, showcasing its architectural details against a twilight sky. Tall cypress trees frame the building, while soft lights outline the windows and entrance, creating a peaceful ambiance amidst the expansive countryside.
Holiday home
4.86 out of 5 average rating, 49 reviews

Prachtig huisje in Tuscany, Luca's House

Enjoy this stylish place, part of three converted farms on the outskirts of the Montecucco wine region. A beautiful panoramic view of the surrounding hills. Imagine yourself with a glass of Brunello or Montecucco, Italian snacks at hand, watching the setting sun. Take a fresh dip in the pool, feel the warmth of the sun and immerse yourself in Italian life. Take the most beautiful day trips to the Val D'Orcia, Bagno Vignoni, Siena, Firenze, Montalcino, Montepulciano and to the sea.

Guest favourite
A contemporary suite is presented with a sleek exterior design, featuring large windows and a shaded terrace. A private hot tub is positioned on a stepped platform, surrounded by greenery. A shaded seating area with an umbrella is visible, along with outdoor lounging options.
Holiday home
5 out of 5 average rating, 17 reviews

Glamping Green Sensations "Suite Diamond"

Benvenuti nella "Suite Diamond" del nostro Glamping 'Green Sensations'. Questo trilocale di 50mq offre comfort lussuosi, due bagni privati e due camere matrimoniali accoglienti, con un divano letto comodamente usufruibile da una persona. Potrete rilassarvi nella vasca idromassaggio esterna e godere della bellezza naturale che ci circonda, con vista sulla natura Toscana. Questa suite è dotata di tavolo in giardino con lettini prendisole, ombrellone e tavolo da Ping-Pong.

Top guest favourite
A narrow alleyway is framed by rustic stone walls, leading down a set of stone steps. Wooden doors with simple handles are visible on either side, while a small balcony with plants is seen above. The sunlight illuminates the steps, creating a warm atmosphere.
Holiday home
4.95 out of 5 average rating, 106 reviews

Siege Alley House

Apartment in the historic center of Pitigliano, one of the most characteristic villages in Italy. A few kilometers from the Terme of Saturnia and Sorano, Lake Bolsena and places of cultural interest. Very special and cozy apartment, bright, with wooden beams, parquet, independent heating, overlooking the valley and the alleys of the village. Consisting of 2 bedrooms, 2 bathrooms, one with a shower and one with a bathtub, a kitchen and a living area.

Superhost
Holiday home
4.85 out of 5 average rating, 39 reviews

Sunny Seaside Cottage

In Monte Argentario, on the stretch of coast that connects Porto Santo Stefano to Porto Ercole, overlooking the sea and with a stunning view of the islands of Giglio and Giannutri, there is this charming autonomous two-room apartment, completely isolated from the view of other homes and the road It consists of a double bedroom, living room with spacious kitchenette and sofa bed , bathroom with shower. In the garden area equipped with barbecue, oven

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