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.

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Top guest favorite

Vacation home in Porto Ercole

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.

LocationFamilyNearby

4.98 out of 5 average rating, 100 reviews

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.

Vacation home in Castiglione della Pescaia

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.

LocationFamilyParking

4.82 out of 5 average rating, 28 reviews

Guest favorite

Vacation home in Marina di Grosseto

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!

LocationValueCheck-in

4.96 out of 5 average rating, 72 reviews

Guest favorite

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

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.

LocationValueQuiet

4.92 out of 5 average rating, 207 reviews

Top guest favorite

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

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.

FamilyLocationBathroom

5.0 out of 5 average rating, 37 reviews

Guest favorite

Vacation home in Saturnia

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.

FamilyValueAir conditioning

4.88 out of 5 average rating, 25 reviews

Top guest favorite

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

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.

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 31 reviews

Guest favorite

A spacious balcony offers views of rolling hills and lush greenery under a clear sky. A table is set with a bottle of wine and a glass, while potted plants add a touch of nature to the setting.

Vacation home in Montiano

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.

LocationNearbyHospitality

4.96 out of 5 average rating, 26 reviews

Guest favorite

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.

Vacation home in Pitigliano

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.

ValueFamilyAmenities

4.93 out of 5 average rating, 111 reviews

Superhost

Vacation home in Porto Santo Stefano

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

ValueFamilyOutdoor spaces

4.86 out of 5 average rating, 42 reviews

Guest favorite

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

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.

LocationPetsQuiet

5.0 out of 5 average rating, 18 reviews

Top guest favorite

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

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.

FamilyValueComfort

4.96 out of 5 average rating, 137 reviews