
Vacation home rentals in Grosseto
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Top-rated vacation home rentals in Grosseto
Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

House on the harbor - Il Partito
Located in the heart of Porto Ercole, on the second floor of a historic building on the waterfront, this vacation home of approximately 70 square meters – completely renovated in 2026 – offers all the charm of the Argentario: a balcony overlooking the harbor with a picturesque view of the sea and the moored boats, a private garden for moments of outdoor relaxation, and a central location, within walking distance of cafés, restaurants, and shops. As the owner of the IDROBOAT dinghy rental, I will be happy to suggest the most beautiful beaches.
4.98 out of 5 average rating, 100 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.
4.82 out of 5 average rating, 28 reviews
Meria di Maria - Pink Villa on the Beach
You'll love this pet- and baby-friendly villa close to the public beach and beach 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 give you advice are the hallmarks of a perfect vacation? In a great location, with everything at your fingertips, you can even leave your car in the parking lot and enjoy your well-deserved relaxation!
4.96 out of 5 average rating, 72 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.
4.92 out of 5 average rating, 207 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.
5.0 out of 5 average rating, 36 reviews
Private villa with swimming pool in Tuscany
Nestled in the hills of Maremma and not far from Tyrrhenian sea, lies the charming, completely immersed in nature with a unique panoramic views.This traditional old stone villa has been beautifully renovated; giving guests the chance to experience Tuscany in all its rustic beauty, in the height of comfort. The Villa is located within the organic farm Fontenuova, a short distance from the hill top town of Saturnia and its famous thermal springs. Your dream holiday awaits for you.
4.88 out of 5 average rating, 25 reviews
Unique & Historic Getaway: Dreamy Garden
This stylish place to stay is perfect for group or family trips, in a small but precious Tuscan village, Montisi, in the Municipality of Montalcino, famous for wine and for being in the Val d'Orcia park, a UNESCO site. The house has a very quiet roof garden, where you can dine and relax after a day spent among the natural, historical and artistic wonders of the area. Each room of Umberto121 is different from the others, having maintained the characteristics of each.
4.97 out of 5 average rating, 30 reviews
Nectar and Ambrosia
Located in the ancient village of Montiano, the apartment enjoys a charming and exclusive view of the Maremma with the rolling hills of Mediterranean scrub and the Morellino di Scansano vineyards. Thanks to its strategic location, you can get to tourist spots such as the Uccellina Park, Talamone, and Argentario in a few minutes. Moving away from the coast, you can visit villages such as Pitigliano, Sorano, Sovana and the famous Thermal Baths of Saturnia.
4.96 out of 5 average rating, 26 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.
4.93 out of 5 average rating, 111 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
4.86 out of 5 average rating, 42 reviews
Glamping Green Sensations "Suite Diamond"
Welcome to the "Diamond Suite" of our 'Green Sensations' Glamping. This 50 sqm three-room apartment offers luxurious comfort, two private bathrooms and two cozy double bedrooms, with a sofa bed comfortably used by one person. You can relax in the outdoor hot tub and enjoy the natural beauty that surrounds us, with views of Tuscan nature. This suite is equipped with a garden table with sun loungers, an umbrella and a Ping-Pong table.
5.0 out of 5 average rating, 18 reviews
In Toscana Camere
**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.
4.96 out of 5 average rating, 137 reviewsPopular amenities for Grosseto vacation home rentals
Family-friendly vacation home rentals

Holiday in an antique farm, Pergola
4.93 out of 5 average rating, 45 reviews
1 bedroom apartment in Tuscan farmhouse
5.0 out of 5 average rating, 53 reviews
Apartment in Maremma "Tuscany"Bio Agriturism
4.91 out of 5 average rating, 22 reviews
Maremma Tuscany in Scarlino - Elegant apartment
4.85 out of 5 average rating, 26 reviews
House for Groups Relax Among Nature and Silence
4.93 out of 5 average rating, 74 reviews
17th century farmhouse Val d'Orcia private pool
4.77 out of 5 average rating, 65 reviews
Appartamento in Val d’Orcia con posto auto privato
4.71 out of 5 average rating, 148 reviews
Independent Historic Sweet House on the Walley.
4.96 out of 5 average rating, 26 reviewsVacation home rentals with a patio

Tuscany, Sorano, Fiordaliso Apartment
4.9 out of 5 average rating, 10 reviews
Prachtig huisje in Tuscany, Luca's House
4.87 out of 5 average rating, 52 reviews
Pian'D'olmo, an ancient farmhouse in the heart of Tuscany
4.9 out of 5 average rating, 31 reviews
Villetta la Fortezza · Tuscan Green Oasis & Relax
5.0 out of 5 average rating, 14 reviews
Polidonia Farmhouse | Relaxation in the Sorano countryside
4.94 out of 5 average rating, 53 reviews
Orchid apartment with terrace
5.0 out of 5 average rating, 10 reviews
attic Albertino 15
4.78 out of 5 average rating, 23 reviews
House in Maremma with Garden, Pool WiFi Tuscany
5.0 out of 5 average rating, 4 reviewsVacation home rentals with a washer and dryer

Montalcino Vacation Home Idolina Guest House
4.97 out of 5 average rating, 29 reviews
Palazzo Palloni: Piano Nobile
4.89 out of 5 average rating, 45 reviews
Casa Monteme, modern loft with views of the Maremma
4.93 out of 5 average rating, 45 reviews
Cozy Cottage with a beautiful view - Casa Luciano
4.88 out of 5 average rating, 24 reviews
Holiday Homes Marina Mono Comfort
4.67 out of 5 average rating, 30 reviews
Montepulciano - Val d'Orcia: home with view

Casa-Vecchia
4.83 out of 5 average rating, 6 reviews
Large country house with outbuilding - 14 people
5.0 out of 5 average rating, 5 reviewsDestinations to explore
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- Vacation home rentals Tuscany
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- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Spiaggia di Capo Bianco
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- La Scarzuola
- Siena Cathedral
- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Necropolis of Tarquinia
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Things to do Grosseto
- Food tours Grosseto
- Outdoors Grosseto
- Tastings Grosseto
- Cooking Grosseto
- Things to do Tuscany
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- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
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- Outdoors Tuscany
- Museums Tuscany
- Workouts Tuscany
- Art workshops Tuscany
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- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Tastings Italy
- Wildlife Italy
- Food tours Italy
- Museums Italy
- Performances Italy
- Wellness Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Landmarks Italy
- Architecture Italy
- Outdoors Italy
- Water sports Italy





