Guesthouse holiday rentals in Province of Grosseto

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Top-rated Guesthouses in Province of Grosseto

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guesthouse in Caldana

4.8 out of 5 average rating, 184 reviews

Appartment 1 surrounded by Tuscan Nature

RobertRating, 5 stars2 months 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

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 favourite

Guesthouse in Petroio

4.96 out of 5 average rating, 122 reviews

LA CASINA: Your tiny house in Tuscany

JanRating, 5 stars2 weeks 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!

Guesthouse in Montieri

4.86 out of 5 average rating, 21 reviews

Podere Rachele - Ghiandaia House

LoïcRating, 5 stars22 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!!

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 favourite

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.

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.

Top Guest favourite

Guesthouse in Solaia

4.94 out of 5 average rating, 31 reviews

Apartment "Cerbaia" in rural house with pool

Welcome to Villa Xavante della Solaia – a large rural 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 around 30 minutes' drive from Sienna (36 km).

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Popular amenities for Province of Grosseto guesthouses

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Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Monte Antico

4.4 out of 5 average rating, 10 reviews

Beautiful Apartment with Pool in Maremma

JessicaRating, 5 stars37 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!

Guesthouse in Caldana

4.8 out of 5 average rating, 184 reviews

Appartment 1 surrounded by Tuscan Nature

RobertRating, 5 stars2 months 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.

Guesthouse in Montieri

4.86 out of 5 average rating, 21 reviews

Podere Rachele - Ghiandaia House

LoïcRating, 5 stars22 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!!

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.

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

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 favourite

Guesthouse in Petroio

4.96 out of 5 average rating, 122 reviews

LA CASINA: Your tiny house in Tuscany

JanRating, 5 stars2 weeks 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!

Private room in Pitigliano

Agriturism Organic (room 4)

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Guesthouse holiday rentals in Province of Grosseto

Top-rated Guesthouses in Province of Grosseto

Holiday rentals for every style

Popular amenities for Province of Grosseto guesthouses

Family-Friendly guesthouses

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