Guesthouse vacation rentals in Province of Grosseto

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Top-rated guesthouse rentals in Province of Grosseto

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A horse stands in a grassy area adorned with wildflowers, while a figure is positioned nearby, creating a harmonious connection with nature. A rustic building is partially visible in the background, surrounded by lush greenery, providing a sense of tranquility.

Guesthouse in Caldana

4.8 out of 5 average rating, 184 reviews

Appartment 1 surrounded by Tuscan Nature

RobertRating, 5 stars1 month ago

We can just highly recommend staying and this place. Dagmar is a great host with plenty of usefuly tipps and amazing activities on site. The house is exactly as described and was perfect for the four of us. It is surrounded by pure nature and a lot of animals (dogs, horses, sheeps etc.) which are superfriendly.

Superhost

A large window frames a view of rolling hills and a distant horizon, allowing natural light to fill the room. A small wooden table with chairs is positioned nearby, complemented by a potted plant and candles on the table.

Guesthouse in Castiglione della Pescaia

4.5 out of 5 average rating, 4 reviews

La Rondine - big windows & pool

NicoleRating, 5 stars8 months ago

We had a great time in this very lovely apartment with a fantastic view! On a rainy day you can cuddle up, have some tea and enjoy the foggy view. The place is great with lots of attention to detail :) The kitchen unit is not shown in the pictures but was good and totally sufficient for some simple cooking👍🏻 We will recommend this airbnb to friends!

Guest favorite

Wooden shelves are displayed against a white wall, showcasing an assortment of pottery. Items include a decorative teapot, various bowls in warm tones, a small white candle, a potted plant, and a mix of colorful mugs and a kettle.

Guesthouse in Petroio

4.96 out of 5 average rating, 122 reviews

LA CASINA: Your tiny house in Tuscany

JanRating, 5 stars1 week ago

Carey was an absolutely amazing host! Her place near the charming village of Petroio, just 10 minutes from Pienza, was the perfect base for exploring the beauty of Tuscany. The house was clear and equipped with everything we needed. Carey was incredibly warm, helpful, and attentive – her local tips made our stay even more special. We truly felt at home and would gladly come back again. Highly recommended to anyone looking for a peaceful and authentic Tuscan experience. Thank you, Carey, for your wonderful hospitality!

A clear blue pool is surrounded by lounge chairs and umbrellas, perfect for sunbathing. Lush green hills rise in the background, dotted with trees and a rustic stone building. The bright sky adds to the serene atmosphere of the space.

Guesthouse in Montieri

4.86 out of 5 average rating, 21 reviews

Podere Rachele - Ghiandaia House

LoïcRating, 5 stars21 months ago

We had a great time, the setting and location allowed us to gather as a family and enjoy the surroundings without stress. ( no noise, the essentials nearby...) The view is beautiful, the pool is very pleasant. The accommodation is functional and spacious enough. Many thanks to Francesco!!

A scenic view showcasing a lush green landscape before a sandy beach. A narrow stream winds through the vegetation, flowing toward the shoreline. In the background, a historic tower rises from the tree line, with the serene blue sea and distant hills visible on the horizon.

Guesthouse in Grosseto

4.77 out of 5 average rating, 26 reviews

Room in Grosseto with wi-fi and air conditioning

The room is located on the 1st floor of a small private building, reached by an internal staircase from a common entrance. Bright, quiet and comfortable, it is located in front of the Mura Medicee, the perimeter of Grosseto's historical centre and the heart of the city, from which you can admire the Cassero Senese. One of the main bus stops is 50 metres away. You can take advantage of a 10% discount at the 'Bastion Contrario' restaurant, which I own very close to the structure.

Top guest favorite

A wine bottle is being poured into a glass, catching the warm hues of a sunset. The landscape of rolling hills and trees is visible in the background, creating a serene atmosphere enhanced by the vibrant colors of dusk.

Guesthouse in Montefollonico

4.97 out of 5 average rating, 103 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

A well-lit room features a spacious bed with clean linens, complemented by a bedside table with a lamp. A wooden door provides access to the room, while neutral-toned walls and flooring add to the calming atmosphere. An air conditioning unit is visible above.

Private room in Caldana

The Decameron - Elissa

The owners of Ristorante Il Boccaccio in the Borgo di Caldana, host you in their guesthouse located just outside the historic centre. The name Boccaccio is inextricably linked to his most famous work: the Decameron. What better term to identify the 4 double rooms, with TV, available near the restaurant? Each room has a name: Fiammetta, Filomena, Lauretta and Elissa. Exactly like some of the girls narrating Boccaccio's novellas. Tradition and innovation.

Guest favorite

The exterior of a rustic stone villa is shown, featuring multiple floors with wooden shutters. A large swimming pool is surrounded by a sun terrace, complemented by vibrant flowers and greenery throughout the landscape. Umbrellas provide shade in designated outdoor seating areas.

Guesthouse in Solaia

4.93 out of 5 average rating, 30 reviews

Apartment "Cerbaia" in rural house with pool

Welcome to the Villa Xavante della Solaia – a large country house in the Tuscan countryside. The house has 4 apartments and apartment "Cerbaia" has entrance from the street. The house includes a pool, a beautiful garden with nice patios – and not least a great view of the Tuscan hills. The property is located about 30 minutes drive from Sienna (36 km).

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Popular amenities for Province of Grosseto guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

An open living area with exposed wooden beams and brick arches is visible. A rustic dining table is centered, complemented by wooden chairs. A cozy seating nook with floral upholstery and a light fixture enhances the space, while a kitchenette can be seen in the background.

Guesthouse in Monte Antico

4.4 out of 5 average rating, 10 reviews

Beautiful Apartment with Pool in Maremma

JessicaRating, 5 stars36 months ago

Beautiful home! The pool and views were incredible. The host was always available and kind in responding to any questions we had. We lived our experience staying here!

The image captures a stone exterior of an apartment at sunset, with a large tree providing shade. Rays of golden sunlight filter through branches, illuminating a grassy area and distant hills. A paved stone path leads towards the entrance, enhancing the connection to nature.

Guesthouse in Caldana

4.8 out of 5 average rating, 184 reviews

Appartment 1 surrounded by Tuscan Nature

RobertRating, 5 stars1 month ago

We can just highly recommend staying and this place. Dagmar is a great host with plenty of usefuly tipps and amazing activities on site. The house is exactly as described and was perfect for the four of us. It is surrounded by pure nature and a lot of animals (dogs, horses, sheeps etc.) which are superfriendly.

A charming stone cottage sits beside a gravel path, surrounded by greenery. Lush hills and patches of clouds create a serene backdrop. The building features a rustic design with large windows, allowing natural light to illuminate the interior.

Guesthouse in Montieri

4.86 out of 5 average rating, 21 reviews

Podere Rachele - Ghiandaia House

LoïcRating, 5 stars21 months ago

We had a great time, the setting and location allowed us to gather as a family and enjoy the surroundings without stress. ( no noise, the essentials nearby...) The view is beautiful, the pool is very pleasant. The accommodation is functional and spacious enough. Many thanks to Francesco!!

The spacious living area features a rustic stone wall and wooden beams overhead. A checkered table sits adjacent to a cozy seating area, which includes a sofa bed and an armchair. Natural light filters through a window, illuminating the tiled floor.

Guesthouse in Montieri

4.72 out of 5 average rating, 18 reviews

Podere Rachele - Owl's House

ChiRating, 5 stars7 months ago

We stayed at Francesco’s place for two nights. It was raining so we didn’t have the full benefit of the area. He was very helpful with everything. However, there aren’t many amenities so come prepared. It was a very comfortable place.

A mobile home is positioned amidst trees, featuring a shaded outdoor area with a small table and chairs. A large umbrella provides additional cover, and a few lounge chairs are placed nearby. The ground is covered with small stones and surrounded by greenery.

Guesthouse in Scansano

4 out of 5 average rating, 5 reviews

Agriturismo Podere Novo 153 - Mobile Home

RobertoRating, 5 stars22 months ago

beautiful place nice staff. top

Superhost

A swimming pool is situated on a raised deck, showcasing clear water that reflects the sky. Surrounding hills and valleys stretch into the distance under a bright blue sky, offering unobstructed scenic views.

Guesthouse in Castiglione della Pescaia

4.5 out of 5 average rating, 4 reviews

La Rondine - big windows & pool

NicoleRating, 5 stars8 months ago

We had a great time in this very lovely apartment with a fantastic view! On a rainy day you can cuddle up, have some tea and enjoy the foggy view. The place is great with lots of attention to detail :) The kitchen unit is not shown in the pictures but was good and totally sufficient for some simple cooking👍🏻 We will recommend this airbnb to friends!

Guest favorite

A cozy bedroom features a spacious bed with soft linens, positioned under wooden beams. Natural light filters through a glass door, illuminating the room. A stylish wooden ladder leans against the wall, while a small table with a flower vase adds a touch of color.

Guesthouse in Petroio

4.96 out of 5 average rating, 122 reviews

LA CASINA: Your tiny house in Tuscany

JanRating, 5 stars1 week ago

Carey was an absolutely amazing host! Her place near the charming village of Petroio, just 10 minutes from Pienza, was the perfect base for exploring the beauty of Tuscany. The house was clear and equipped with everything we needed. Carey was incredibly warm, helpful, and attentive – her local tips made our stay even more special. We truly felt at home and would gladly come back again. Highly recommended to anyone looking for a peaceful and authentic Tuscan experience. Thank you, Carey, for your wonderful hospitality!

A room features warm brown tones and wooden accents, including a low, wooden bed dressed in a vibrant orange coverlet. Soft lighting is provided by two bedside lamps and a paper lantern hanging from the ceiling. A mirror and a small framed artwork add a touch of decor.

Private room in Pitigliano

Agriturism Organic (room 4)

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Guesthouse vacation rentals in Province of Grosseto

Top-rated guesthouse rentals in Province of Grosseto

Vacation rentals for every style

Popular amenities for Province of Grosseto guesthouse rentals

Family-friendly guest house rentals

Destinations to explore