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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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Guest favourite
Holiday home in Castiglione della Pescaia
4.81 out of 5 average rating, 26 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 in Porto Ercole
4.98 out of 5 average rating, 90 reviews

House on the harbor - Il Partito

Nel cuore di Porto Ercole, al primo piano di un palazzo storico sul lungomare, questa casa vacanze di circa 70 mq - completamente ristrutturata nel 2026 - offre tutto il fascino dell'Argentario: un balcone affacciato sul porto con vista suggestiva sul mare e sulla barche ormeggiate, un giardino privato per momenti di relax all'aperto e una posizione centrale, a pochi passi da bar, ristoranti e negozi. Come proprietaria del noleggio gommoni IDROBOAT, sarò lieta di suggerirvi le spiagge più belle.

Top guest favourite
Holiday home in Montepulciano
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
Holiday home in Monticchiello
5 out of 5 average rating, 36 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
Holiday home in Massa Marittima
4.93 out of 5 average rating, 119 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
Holiday home in Montemerano
4.93 out of 5 average rating, 44 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.

Superhost
Holiday home in Monte Cucco
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
Holiday home in Scarlino
5 out of 5 average rating, 18 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.

Superhost
Holiday home in Porto Santo Stefano
4.85 out of 5 average rating, 39 reviews

Sunny Seaside Cottage

In Monte Argentario, in the stretch of coast that connects Porto Santo Stefano to Porto Ercole , overlooking the sea and with a breathtaking view of the islands of Giglio and Giannutri , there is this charming two-room independent apartment,completely isolated from the view of other houses and the street It consists of double bedroom, living room with spacious stove top and sofa bed , bathroom with shower. In the garden area equipped with grill , oven

Top guest favourite
Holiday home in Pitigliano
4.95 out of 5 average rating, 108 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 in Manciano
5 out of 5 average rating, 3 reviews

The House in Piazza [Super terrace-18' from the Spa]

Scopri un'esperienza unica a Manciano scegliendo questo incantevole appartamento situato nel cuore del centro storico. Goditi una posizione strategica, utile per raggiungere con facilità tutte le principali attrazioni. L'appartamento si trova a soli 20 minuti dalle Terme di Saturnia, dove potrai rilassarti tra le acque termali naturali. Ti aspetta un ambiente accogliente e confortevole, con una spaziosa terrazza che offre una vista mozzafiato.

Top guest favourite
Holiday home in Monticchiello
4.96 out of 5 average rating, 135 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

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