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House holiday rentals in Province of Grosseto

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Province of Grosseto

House rentals with a pool

Guest favourite
Home in Buonconvento
4.97 out of 5 average rating, 87 reviews

S.Ilaria - Private pool Villa with 2 bedrooms

AlisonRating, 5 stars3 weeks ago
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!
Top guest favourite
Home in San Giovanni d'Asso
5 out of 5 average rating, 62 reviews

Country chic house in a village,private pool,wiFi

PennyRating, 5 stars1 month ago
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!
Guest favourite
Home in Grosseto
5 out of 5 average rating, 15 reviews

Fattoria Tolomei Casa di Pietra

AnneRating, 5 stars3 days ago
We had a great stay. The house matches the description very well and is perfectly equipped. Consuelo was super responsive and helpful and even brought us some olive oil and lettuce from the farm ☺️
Superhost
Home in Sant'Antonio
4.82 out of 5 average rating, 28 reviews

House with private pool

RonaldRating, 5 stars9 months ago
Wij hebben genoten van ons verblijf bij Maria Teresa. De tuin is echt fantastisch en mooi onderhouden. Je kan er op verschillende plekjes zitten, er is zelfs een buitenkeuken met ijskast ,vriezer en gasfornhuis. Het zwembad is superschoon en wordt elke ochtend schoon gemaakt. Het huis zelf is ook heel fijn, koel en van alle gemakken voorzien. De omgeving is zeer rustig en voor natuurliefhebbers genoeg wild te spotten op 2 minuten lopen. Wij hebben herten, zwijnen, vossen en zelfs een wolf gespot. echt geweldig! Het bordje poolside paradise staat er niet voor niks, het is echt een paradise! We raden het zeker aan en als wij weer in de buurt zijn komen we zeker terug! Maria Teresa hartelijk dank voor alles!
Top guest favourite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Guest favourite
Home in Roccastrada
5 out of 5 average rating, 5 reviews

Apartment in the countryside

Dr. SveaRating, 5 stars10 months ago
Außergewöhnlich schöne, mit viel Liebe und Geschmack eingerichtete Wohnung in einer wunderschönen, gepflegten Anlage! Der schöne, gepflegte Pool ist das i-Tüpfelchen, das die Anlage perfekt macht. Wir haben das viergängige Dinner unter Sternen sehr genossen, in der Umgebung gibt es aber auch so viele gute Restaurants, dass man gar nicht alle ausprobieren kann. Chiara und Stefano sind die perfekten Gastgeber, von ihnen kann man viel Interessantes erfahren! Sie legen auch viel Wert auf Nachhaltigkeit, die Anlage ist autark und im zugehörigen Weingut werden nur Bio-Weine produziert.
Superhost
Home in Scansano
4.84 out of 5 average rating, 62 reviews

Il Casaletto nel cuore della maremma

OlivierRating, 5 stars10 months ago
Wow, what a peaceful place ! And that view 🤩 If you’re looking for a quiet environment to disconnect while enjoying nature and small medieval town walks (and taste good wines) this is the right place ! Ginevra is a very careful host, always looking to take care of you whatever happens, you will feel very supported !
Top guest favourite
Home in Chiusdino
4.91 out of 5 average rating, 45 reviews

La Capanna: country house with magnificent view

VitaliyRating, 5 stars1 month ago
Amazing place to stay, a great host and beautiful surroundings!

Weekly house rentals

Top guest favourite
Home in Castiglione d'Orcia
4.96 out of 5 average rating, 94 reviews

Da nonna Ornella - nido in Val d’Orcia

준우Rating, 5 stars4 days ago
의사소통이 약간 아쉬운것 빼곤(이것도 번역기를 통해서 의사소통 가능)정말 최고의 숙소였습니다 위치부터 호스트까지 모두 만점을 드리고 싶어요 환상적인 풍경과 따뜻하고 배려심 넘치는 상냥한 디바가 있어서 우리의 허니문이 완벽했습니다 너무 멀지만 기회가 된다면 꼭 다시 오고 싶습니다 우리에게 최고의 경험을 선사해준 디바에게 존경과 감사와 경의를 표합니다 당신은 정말 최고에요, 디바!
Top guest favourite
Home in Sticciano Scalo
4.95 out of 5 average rating, 39 reviews

Villetta in Maremma

VickyRating, 5 stars8 months ago
Massimo and his wife were great hosts. His place was ready and clean when we arrived. It had everything we needed. Massimo was always responsive and helpful. We were staying there for a wedding at La Pescaia and Massimo was kind enough to give us rides when needed. He went above and beyond to make us feel at home. I highly recommend Massimo’s place and would love to visit again. Thank you Massimo and Luana!
Top guest favourite
Home in Bivio di Ravi
4.96 out of 5 average rating, 54 reviews

Casa Elicriso

FrancescoRating, 5 stars1 week ago
Abbiamo trascorso un soggiorno fantastico grazie all'ospitalità e all'entusiasmo di Barbara e Emmanuele, che hanno avuto la gentilezza di trascorre dei momenti indimenticabili con noi, nonostante i loro obblighi lavorativi. L'appartemento è impeccabile : pulito, ordinato e ben organizzato. La loro casa è ben situata nella Toscana meridionale, poco distante da centri culturali e archeologici come vetulonia, massa marittima o Grosseto. Belle spiagge son a solo 1/4 d'ora, 20 mn di macchina come Follonica o Castiglione. Insomma se passate in zona, veramente non esitate, fiondatevi ! una caro abbraccio Brenda & Francesco
Top guest favourite
Home in Monticchiello
5 out of 5 average rating, 41 reviews

Graziosa abitazione per sognare

CadeRating, 5 stars6 days ago
This place is definitely a piece of Tuscany Italy. it will always hold a special place in my wife's and my heart with how beautiful and amazing the house was and the town it is located in. it seemed very well located, close to hot springs, multiple other cities, beautiful country side with horse back riding, world class winery's, ect. She is a great host and I would highly recommend this Airbnb to anybody looking for a one of a kind experience in Italy.
Top guest favourite
Home in Castell'Azzara
5 out of 5 average rating, 82 reviews

La Bandita dei Bovi

KarolinaRating, 5 stars2 weeks ago
We had a wonderful stay at La Bandita! Debora is an amazing host who takes care of every detail. We were welcomed with thoughtful gifts – wine, pasta, homemade jams – a true taste of Tuscany. The house is beautifully equipped: spices, oils, kitchen tools, ice cubes, even toothbrushes and soaps in the bathroom. Extra towels, cozy blankets, and everything we could possibly need were provided. The location is peaceful and picturesque, perfect for relaxing and enjoying the Tuscan countryside. Breakfasts on the terrace with the panoramic view were unforgettable. Communication with Debora was excellent – she was kind, responsive, and made us feel at home. We truly felt taken care of and appreciated every moment spent there. La Bandita is a magical place, full of warmth and charm. We’d love to return one day – it felt like a home away from home, and we can’t recommend it enough to anyone looking for an authentic and comfortable Tuscan getaway. We'd love to come back!
Top guest favourite
Home in Montalcino
5 out of 5 average rating, 8 reviews

New Palazzo in City Center: 4 King Bedrms 6 Bath

FrancescaRating, 5 stars5 months ago
Palazzo Tamanti ha pienamente soddisfatto tutte le nostre aspettative !! Cercavamo un luogo perfetto e denso di atmosfera per trascorrere un capodanno magico e particolare : quest'anno abbiamo trovato il top !! Abbiamo amato ogni angolo di questa residenza , ristrutturata da poco e dotata di tutti i confort ... Materassi, guanciali, piumoni e imbottiti superlativi !! Non ho mai dormito così bene... A palazzo Tamanti ogni dettaglio è curato al massimo e ogni ospite si sente coccolato dall'inizio alla fine del soggiorno.... Impianto elettrico sopraffine, tutte le dotazioni tecnologiche sono perfettamente funzionanti e di livello elevato, le quasi 200 foto presenti sul sito sono perfettamente rispondenti alla realtà. L'accoglienza da parte dell'host Valentina è stata perfetta, sempre gentile e disponibile. La casa è situata in pieno centro storico , per cui tutto è a portata di mano e si può raggiungere a piedi. Cari Brian, Carrie e Valentina, grazie di tutto !!
Guest favourite
Home in Contignano
4.95 out of 5 average rating, 19 reviews

Noi 2 Vacanze in Fortino d'Amore

MikeRating, 5 stars1 month ago
This was a wonderful space with amazing history of the Val d'Orcia. Giuseppe was a delight showing us everything we needed to know in this very well appointed two story unit. The bed was extremely comfortable and the hosts went to great lengths to supply everything we could need, especially the Illy coffee and moka pot for espresso. Having the clothes washer was a big plus. The views from every window are breathtaking and the location is a perfect balance of feeling out in the country while close to tourism sites. Have a car was very useful. The unit sits amongst many making it feel like a little quaint and quiet town with a small grocery steps away. We were very fortunate to have found this place and would recommend to anyone as something very special and quietly romantic.
Guest favourite
Home in Montalcino
4.94 out of 5 average rating, 33 reviews

Domus Antiqua

KellyRating, 5 stars1 month ago
We loved staying in this beautiful home in Montalcino. It was even more beautiful and unique than the pictures! My family of five loved staying here- lots of space for everyone and it was fun to be right in the 500 year old town. We especially love having coffee and wine on the balcony.

Private house rentals

Guest favourite
Home in Monte Argentario
4.91 out of 5 average rating, 74 reviews

Villino "alla vigna"

AntjeRating, 5 stars1 day ago
Eine wunderschöne Unterkunft, die einen Rundumblick auf das Meer ermöglicht. Wunderbare Sonnenauf-untergänge, ruhig - wir konnten sogar den Wiedehopf beobachten und im Garten die reifen Aprikosen und Pflaumen naschen. Francesco ist ein äußerst zuvorkommender Gastgeber und hat sich viel Mühe gegeben und immer wieder nachgefragt, ob alles passt. Im Haus hat es alles, was man benötigt, die Küche super eingerichtet und das eigene Olivenöl ist sehr fein. Die Anfahrt ist auch mit einem größeren Auto - wir haben einen Citroen Berlingo - möglich.
Top guest favourite
Home in Campiglia D'orcia
5 out of 5 average rating, 22 reviews

Casa Letizia: Val d'Orcia, Terme e Monte Amiata

FilipaRating, 5 stars1 month ago
Our family had a wonderful stay at Letizia’s accommodation. The beauty of the home and surrounding valley exceeded the photos and description. We felt so welcome and at home and had plenty to do from walking on the farm to visiting the many surrounding towns. Letizia recommended a local restaurant which was superb. Letizia helped us immensely with any question we had and it was a big highlight of our trip to Europe. Thank you Letizia!
Guest favourite
Home in Manciano
4.94 out of 5 average rating, 18 reviews

La Civetta • iBorgorali

AmélieRating, 5 stars2 months ago
We had a wonderful stay! The location is absolutely beautiful – peaceful, scenic, and just perfect for a relaxing getaway. Arianna was excellent at communicating and responded quickly to any questions or concerns I had. Highly recommend!
Guest favourite
Home in Montalto di Castro
5 out of 5 average rating, 7 reviews

Seafront Cottage on Maremma Beach

AndreaRating, 5 stars1 month ago
Ein Traumhafter Ort zum Ausspannen. Wir suchten Ruhe und Erholung und kamen voll auf unsere Kosten. Ein schönes Haus mit Meerblick und Meeranstoss. Wir bekamen rasche Hilfestellung als wir eine Schraube benötigten, die wir an einem Gerät von uns verloren hatten.
Top guest favourite
Home in Montepulciano
4.95 out of 5 average rating, 21 reviews

Hortus Conclusus House

MichelleRating, 5 stars1 week ago
Apartment was centrally located in the town. Very walkable to shops and restaurants. Beautiful sunrises through bedroom window. Very responsive hosts, especially with getting to the apartment from the train station (no Uber or taxi services when we arrived, so my advice is to get off at the previous stop if coming from Florence or make advance taxi arrangements). The hosts were very helpful and called their go-to cab driver. Beautiful with town and can’t wait to return!
Top guest favourite
Home in Pienza
5 out of 5 average rating, 54 reviews

Pienza Center - Stylish Apt, 6 Guests, A/C & WiFi

AaronRating, 5 stars3 days ago
One of the nicest places I’ve stayed. Like a luxury well decorated boutique hotel. But in Tuscany! We were 3 couples, each had their own room and bathroom.
Superhost
Home in Porto Santo Stefano
4.88 out of 5 average rating, 58 reviews

Villetta Sassi Verdi

NathanRating, 5 stars8 months ago
Très beau logement, hôte réactif, très attentionné et aidant, répond très rapidement si besoin. Environnement calme, paisible, éloigné de Porto Santo Stefano mais compensé par une vue paradisiaque. Les très gros atouts sont le solarium, la vue spectaculaire de la terrasse, la plage privée à 1km. Malgré nos 2h de retard à l’arrivée, nous avons été très bien accueillis par Marco et sa femme. Ils ont de plus accepté de venir plus tôt à notre départ pour des questions organisationnelles. Nous recommandons à 100% et nous reviendrons.
Top guest favourite
Home in Roccastrada
5 out of 5 average rating, 81 reviews

Delizioso loft immerso nel verde con giardino

ChiaraRating, 5 stars6 months ago
È stato un soggiorno più che piacevole. La casa di Ezio e Angela è un piccolo paradiso in mezzo alla natura. Siamo stati accolti come persone di casa. La comunicazione è stata ottima, facile e di buoni consigli. Ho apprezzato molto una grande flessibilità nei check in e out che ci hanno resi indipendenti. Tutto davvero ottimo! Assolutamente ritorneremo! Comodissima per raggiungere le fonti termali di Petriolo: poco meno di una mezz oretta di macchina in mezzo alla campagna.

Destinations to explore

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  4. Province of Grosseto
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