Vacation home rentals in Province of Grosseto

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in Province of Grosseto

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

0 of 0 items showing

1 of 3 pages

Guest favorite

An inviting living area showcases original wooden beams and a stone accent wall. A spacious purple sofa is positioned near a wooden dining table, surrounded by four chairs. The kitchen features warm-toned tiles and modern appliances, with natural light filtering through a window offering a scenic view.

Vacation home in Pitigliano

4.88 out of 5 average rating, 85 reviews

Il Carisma

"Il Carisma" is a typical Tuscan house, characterized by tuff inserts and original wooden beams from the 1600s. It is spread over a single floor and therefore well suited for children and the elderly. It consists of a large living area, a kitchen equipped with a stove top, a private bathroom, and a bedroom. Located at the beginning of the historic center, Il Carisma offers a panoramic view of the valley and the picturesque Londini Waterfall and is just a few meters from parking lots and restaurants.

Guest favorite

A small outdoor area is featured with a stone wall and terracotta flooring. A wicker chair and a round side table are positioned, with a potted plant on the ledge. The view beyond shows greenery leading to the beach and the sea in the distance.

Vacation home in Giglio Porto

4.82 out of 5 average rating, 34 reviews

Giglio_White

Un delizioso e completissmo monolocale sulla bellissima spiaggia delle Cannelle. Per una strepitosa vacanza di coppia, con la possibilità di un ulteriore posto letto, ho piacere di ospitarvi a Giglio_White. Questo luogo è una vera perla: la vicinanza con la spiaggia, la tranquillità, la privacy, vari posti auto gratuiti adiacenti la casa, il giardino, la veranda con tavolo per mangiare sotto l'incomparabile cielo gigliese, lo scorcio sull'incantevole mare. Io sono Michelangelo e Voi i benvenuti!

Superhost

A traditional Tuscan farmhouse is set against a backdrop of rolling hills, characterized by vibrant earthy tones. Cypress trees line the winding path leading to the home, while the fields are bathed in warm sunlight, creating a serene rural landscape.

Vacation home in Torrenieri

4.67 out of 5 average rating, 88 reviews

Apartment in Val d'Orcia with private parking space

Our apartment is located in Torrenieri (SI) fraction of Montalcino, close to many tourist attractions such as: San Quirico d'Orcia, Terme di Bagno Vignoni, Montalcino, Buonconvento & San Giovanni d'Asso, it is also at the Via Francigena about 1,500 meters from the famous cypresses of S. Quirico d'Orcia. It is a comfortable, welcoming and well-organized apartment, located on the ground floor with a private parking space. Perfect for a holiday in Val d'Orcia! Ps: 2 Bicycles available upon request

Guest favorite

A serene view of the lush green valley is displayed, framed by historic stone buildings. The sky is filled with clouds, and foliage is visible in the foreground, enhancing the natural setting. A sense of tranquility emanates from this outdoor vantage point.

Vacation home in Pitigliano

5 out of 5 average rating, 7 reviews

Independent Historic Sweet House on the Walley.

Rilassati e ricaricati in quest'oasi di quiete ed eleganza nel centro storico di Pitigliano, all’interno della Piccola Gerusalemme con vista sul verde della vallata. Adatto alle famiglie con la zona giorno, l’angolo cucina e l’ampia zona notte al piano superiore. Siamo pet friendly 🐶❤️ Il bagno, da poco ristrutturato, e’ confortevole con una comoda doccia a parete 70x120, l’angolo lavabo dalla parte opposta. Adatto anche per lo smart-working con un angolo lavoro e Wi-Fi illimitato.

Guest favorite

Vacation home in San Giovanni d'Asso

4.91 out of 5 average rating, 35 reviews

Refined house with pool, Valdorcia Deluxe 2

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

Guest favorite

An outdoor shower is attached to a stone wall, surrounded by lush greenery. A well-maintained stone path leads towards it, bordered by vibrant red flowers, adding a touch of color to the natural setting.

Vacation home in Porto Santo Stefano

4.71 out of 5 average rating, 160 reviews

Rossini Cottage

Small cottage with a double bed, for a romantic escape from the town. The cottage is provided with bathroom, external kitchen, private garden with barbecue and external spaces for romantic dinners. It's right only and exclusively for two people. Breathtaking sea sight!! The street to reach the cottage is winding enough, suitable for expert drivers, this is the price to be paid to enjoy peace and rest. Taxi service possible Its not a spot for everybody!! Only couple in love Please!!

Top guest favorite

A small balcony area is visible through sliding glass doors, featuring a wooden table and two chairs overlooking the marina. The tranquil water and moored boats create a serene backdrop, while bright skies enhance the inviting atmosphere of the space.

Vacation home in Porto Ercole

4.97 out of 5 average rating, 39 reviews

House on the harbor - Il Partito

In the heart of Porto Ercole, on the seafront, this charming vacation home of about 70 square meters is for rent, located on the first floor. Its balcony overlooking the harbor offers a striking view of the sea and moored boats, immersing you in the magical atmosphere of Argentario. Thanks to its privileged location, bars, restaurants and shops are a short walk away. As the owner of the IDROBOAT dinghy rental, I will be happy to suggest the most beautiful beaches.

Superhost

A patio dining area features a glass-top table surrounded by four wicker chairs. The space offers unobstructed views of the sea and nearby islands, set against a backdrop of a clear blue sky and lush greenery.

Vacation home in Porto Santo Stefano

4.83 out of 5 average rating, 35 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

Guest favorite

A rustic house is positioned on a grassy hillside, surrounded by olive trees. The building features a blend of stone and stucco, with a terracotta roof. A clear blue sky with wispy clouds enhances the serene landscape.

Vacation home in Canino

4.9 out of 5 average rating, 48 reviews

Namaste Apartment, sea, lake and Terme di Vulci

Namaste vacation home, silence in nature. Beautiful rest with a wide view of the olive grove, incredible sunset and starry night sky. We are in the right place to reach so many beautiful places: Terme di Vulci and Saturnia, Lake Bolsena, the sea in Montalto and the last beach of Tuscany, the Etruscan necropolis of Tarquinia, Capalbio, the Tarot Garden, Tuscania, the Hermitage of Poggio Conte, the Cathedral of Orvieto and Civita di Bagnoregio.

Superhost

An outdoor terrace is featured, showcasing a table surrounded by four iron chairs with cushioned seating. A patterned tablecloth covers the table, and vibrant flowerpots add a touch of color to the space. The brick walls and tiled floor enhance the inviting atmosphere.

Vacation home in Torrenieri

5 out of 5 average rating, 4 reviews

Orchid apartment with terrace

Apartment located in Torrenieri, a hamlet of Montalcino, equipped with every comfort to spend an excellent vacation or for work. Great location to visit the main villages Val d 'Orcia (San Quirico, Pienza, Montepulciano, Monticchiello). Guests have exclusive use of the apartment located on the second floor with individual access via external stairs. There is a terrace where you can recharge in thisquiet and elegant space.

Superhost

A large swimming pool is surrounded by a sun terrace featuring lounge chairs. A rustic stone building is visible in the background, complemented by a shaded seating area made of wood. Lush greenery adds to the serene outdoor space.

Vacation home in Radicofani

4.79 out of 5 average rating, 48 reviews

17th century farmhouse Val d'Orcia private pool

Typical Tuscan 17th century farmhouse with exposed beams in Val d'Orcia. Two rooms with fireplaces, five bedrooms, 5 bathrooms. Two equipped kitchens. Garden with private games for children. Large private swimming pool. Il Casale is located just 2 km from Radicofani and where you will find a supermarket, bakery, bars, restaurants, butcher and bank

Superhost

A panoramic view showcases rolling hills and lush greenery, dotted with olive trees under a partly cloudy sky. The landscape extends towards the horizon, embodying the serenity of the surrounding countryside.

Vacation home in Montepulciano

4.92 out of 5 average rating, 24 reviews

Villa Fè: Jacuzzi, View and Space for 7 Guests

Welcome to our charming villa, located just 1 km from the historic center of Montepulciano, a true Tuscan gem. The second-floor apartment is perfect for groups or families of up to 7 people (plus a crib), offering everything you need for an unforgettable vacation in total comfort and tranquility.