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Vacation home accommodations in Grosseto

Find and book unique vacation houses on Airbnb

Top-rated vacation houses in Grosseto

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

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Top guest favourite
Vacation home in San Giovanni d'Asso
4.94 out of 5 average rating, 110 reviews

Elegant house with pool, Valdorcia Deluxe 1

In the Val D'Orcia DELUXE apartments, you can relax in the midst of nature in a spacious and very welcoming home. The house is equipped with everything you need (including a dishwasher, washing machine, microwave, wifi, Playstation) and has large outdoor spaces with a swimming pool, gazebos, LCD TV, tables, sofas. You will be followed by booking until your arrival with all the useful information and of course we will always be at your disposal throughout the stay. I look forward to seeing you soon!

Guest favourite
The exterior of the stone house is featured, showcasing rustic charm with green shutters and a welcoming entrance. The garden area includes tables and chairs, surrounded by lush greenery and potted plants, offering a serene outdoor space for relaxation.
Vacation home in Montisi
4.96 out of 5 average rating, 24 reviews

Unique & Historic Getaway: Dreamy Garden

Questo elegante alloggio è perfetto per viaggi di gruppo o familiari, all'interno di un piccolo, ma prezioso borgo toscano, Montisi, nel Comune di Montalcino, famoso per il vino e per essere nel parco della Val d'Orcia, sito UNESCO. La casa ha un giardino pensile molto tranquillo, dove poter cenare e rilassarsi dopo una giornata passata tra le meraviglie naturali, storiche ed artistiche della zona. Ogni stanza di Umberto121 è differente dall'altra, avendo mantenuto le caratteristiche di ognuna.

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.
Vacation home in Montepulciano
4.92 out of 5 average rating, 191 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.
Vacation home in Monticchiello
5 out of 5 average rating, 24 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.
Vacation home in Massa Marittima
4.93 out of 5 average rating, 106 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.
Vacation home in Montemerano
4.92 out of 5 average rating, 37 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.
Vacation home in Sorano
4.91 out of 5 average rating, 32 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.

Top 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.
Vacation home in Scarlino
5 out of 5 average rating, 15 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
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.
Vacation home in Monte Cucco
4.84 out of 5 average rating, 44 reviews

Prachtig huisje in Tuscany, Luca's House

Enjoying this stylish place, part of three converted farms at the edge of the Montecucco wine country. A beautiful view of the hills all around. Imagine yourself with a glass of Brunello or Montecucco, Italian bites at hand, looking at the setting sun. Take a refreshing dip in the pool, feel the warmth of the sun, and get up 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
The living area features exposed wooden beams above, with light streaming in through multiple windows. A striped sofa and two green chairs provide seating. A decorative fireplace is situated next to a side table, complemented by warm terracotta flooring.
Vacation home in Pitigliano
4.95 out of 5 average rating, 96 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
Vacation home in Grosseto
5 out of 5 average rating, 3 reviews

Pianferrari Agriturismo in Maremma

Experience the authentic Maremma in our agriturismo! Surrounded by nature, our apartment offers relaxation and comfort: a cozy bedroom, a fully equipped kitchen, a private outdoor space with a barbecue. Ideal for couples, families, or friends, it’s the perfect base to explore villages like Pitigliano, Saturnia, and the Parco della Maremma. Enjoy local products such as wine, olive oil, and organic honey. Book your slice of paradise in Tuscany now!

Top guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Vacation home in Monticchiello
4.97 out of 5 average rating, 118 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.

Popular amenities for Grosseto vacation houses

Destinations to explore

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  2. Italy
  3. Tuscany
  4. Grosseto
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