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House vacation rentals in Province of Grosseto

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Popular amenities for Province of Grosseto house rentals

House rentals with a pool

Top guest favorite
A serene outdoor space features a rectangular swimming pool surrounded by a lush green lawn. Four lounge chairs in soft pink are positioned nearby, offering a view of the expansive countryside and distant hills under a partly cloudy sky.
Home in Buonconvento
4.97 out of 5 average rating, 87 reviews

S.Ilaria - Private pool Villa with 2 bedrooms

AlisonRating, 5 stars1 week 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!
Guest favorite
A spacious balcony offers panoramic views of the sea and distant coastline, where boats are visible in the harbor below. The vibrant blue of the water contrasts with the sky, creating a serene backdrop. Comfortable seating is arranged for relaxation while enjoying the scenery.
Home in Porto Santo Stefano
4.75 out of 5 average rating, 44 reviews

Stunning new house with amazing sea view and pool

EthanRating, 5 stars5 days ago
One of the best views you will find! Place is clean and comfortable. AC in every room and worked well. Probably the best washer dryer we had in Italy :) Incredibly responsive host. Highly recommend!
Top guest favorite
A warm guest room features a spacious bed adorned with a patterned coverlet. Two bedside lamps illuminate the area, beside a wooden chair and a small dresser. A large painting hangs on the wall, while a window offers natural light, showcasing rustic decor elements.
Home in Chiusdino
5 out of 5 average rating, 27 reviews

Il Camino: cosy & artfully inspired country house

MildredRating, 5 stars3 weeks ago
Thomas was so sweet and helpful. He was an absolute gentleman and wonderful host. The views were amazing. Very homey and decorated in the Tuscany style. Close to town but perfect for a quiet escape in the Tuscan countryside.
Superhost
A large swimming pool reflects the blue sky, surrounded by an expanse of green lawns and trees. Sun loungers are positioned nearby, offering space for relaxation. Rolling hills in the background create a natural setting, enhancing the tranquil atmosphere of the area.
Home in Scarlino
4.82 out of 5 average rating, 11 reviews

3 rooms in the woods, with swimming pool - Fonte di Sotto

GérardRating, 5 stars10 months ago
Margherita is very welcoming, good tips for the must-sees of the region, we had a very pleasant stay, comfortable bedding, spacious and well arranged house, a splendid swimming pool with views (about 20m long), lots of sunbed, air conditioning everywhere. So yes, the dirt road to get there may seem long sometimes but that's the price of tranquility. Only downside, the risk of having noisy neighbors on the lower or upper floor (which we had for 3 days).
Superhost
The image showcases three distinct scenes: a rustic house surrounded by greenery, a kitchen area with fresh fruits on the counter, and a serene outdoor pool area with sun loungers. A fourth scene features riders on horseback traversing a sunlit landscape, highlighting the rural setting.
Home in Scansano
4.73 out of 5 average rating, 62 reviews

Independent house "Lo Zoppolino"

Rose MarieRating, 5 stars1 month ago
My husband and I in this little house that is a few meters from the main former barn have regenerated and unplugged. Very old, renovated in an incredible way, with a kitchen equipped with all hot water and a nice little bed. Minimum spaces but great for 2. In an enchanted forest very well cared for and close to the beautiful horses of Andrea, excellent horse riding and respectful of animals. The farm can be reached with a 1 km dirt road that is good for off-road or not too low cars, we traveled every day with a Pole. We were at the end of May and early June so we found some rains but fortunately many sunny days too. We were surrounded by greenery with a refreshing silence for us coming from the city. He bought fantastic food and meat from Federico in the nearby village Scansano enchanting and then the black wine given by Andrea . and the cake that is good. We often went to the thermal baths of Saturnia top and a few days to the beach. A lent
Top guest favorite
A private pool is situated on a sunlit terrace, surrounded by lush greenery and rolling hills. Four lounge chairs are positioned nearby, inviting relaxation. The tranquil water of the pool reflects the surrounding natural landscape, creating a serene outdoor space.
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 stars3 weeks 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 favorite
An inviting outdoor area features a swimming pool surrounded by well-tended greenery. A spacious terrace with wooden seating overlooks the pool, offering a tranquil view of the rolling hills. Sun loungers are positioned nearby, creating a relaxing atmosphere.
Home in Grosseto
5 out of 5 average rating, 14 reviews

Tolomei Farmhouse in Stone

NatalieRating, 5 stars3 months ago
Everything is great, great place to stay with a small wellness area. We felt very comfortable!
Top guest favorite
A charming stone house is situated beside a serene swimming pool, surrounded by lush greenery. Poolside sun loungers and umbrellas are positioned along the terracotta patio, offering a relaxing outdoor space. The clear blue sky and soft clouds enhance the tranquil atmosphere.
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars3 weeks 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!

Weekly house rentals

Guest favorite
A spacious yellow building is surrounded by well-maintained greenery and trees. The structure includes a balcony on the upper level, while the lower section features a covered porch area. A paved pathway leads to the entrance, providing a welcoming access to the property.
Home in Grosseto
4.82 out of 5 average rating, 73 reviews

Casa Allegra

SimoneRating, 5 stars1 month ago
Clean, spacious, and tidy. In a strategic position to visit all the surrounding areas. Super kind and helpful hosts, so much to accompany us on a visit to the Maremma Park to fully experience it thanks to the presence of a native
Top guest favorite
A cozy dining area is seen through open double doors, revealing a view of the green garden outside. Wooden chairs surround a table, while a rustic cabinet adds to the charm of the space. Natural light enhances the warm ambience.
Home in Castiglione d'Orcia
4.96 out of 5 average rating, 92 reviews

Da nonna Ornella - nest in Val d'Orcia

FabienneRating, 5 stars2 days ago
Diva has a charming accommodation here in the beautiful Toscana ☀️ A successful surprise made our short stay perfect ☺️
Top guest favorite
The charming exterior of a quaint house is displayed, featuring two arched windows adorned with wooden shutters. A welcoming wooden door is centered at the entry. Flower pots filled with greenery are placed near the entrance, enhancing the inviting atmosphere of the home.
Home in Sticciano Scalo
4.95 out of 5 average rating, 38 reviews

Villa in Maremma

VickyRating, 5 stars7 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 favorite
A vibrant yellow house stands amidst greenery, featuring multiple windows with dark shutters. A hammock is stretched between two trees, offering a relaxing spot. In the foreground, a dining set with chairs is visible, providing an outdoor seating area surrounded by grass.
Home in Bivio di Ravi
4.96 out of 5 average rating, 52 reviews

Casa Elicriso

FrancescoRating, 5 stars2 days ago
We had a fantastic stay thanks to the hospitality and enthusiasm of Barbara and Emmanuele, who were kind enough to spend unforgettable moments with us, despite their work obligations. The apartment is impeccable: clean, tidy and well organized. Their house is well located in southern Tuscany, not far from cultural and archaeological centers such as Vetulonia, Massa Marittima, or Grosseto. Beautiful beaches are only 1/4 of an hour, 20 minutes by car, such as Follonica or Castiglione. In short, if you pass through the area, really don't hesitate, go for it! Warmest regards, Brenda & Francesco
Top guest favorite
A rustic kitchen area is nestled against a stone wall, featuring a wooden bar table with two round stools. Minimalistic shelves hold kitchen essentials, while light streams through a window, illuminating the space and connecting it with the adjoining sleeping area.
Home in Montemassi
4.96 out of 5 average rating, 48 reviews

Capezzuolo 33

MathildeRating, 5 stars1 week ago
Amazing. We fell in love with Tuscany and with Montemassi. Lucia and Marco’s place is a little cozy nest in the most beautiful surroundings. If you like wine, you’ll be happy with all the beautiful wineries nearby. Would definitely come back! Thanks to Lucia and Marco for the amazing welcome and for their attention to detail!
Top guest favorite
Rustic wooden windows are open, framing a scenic view of rolling hills, cypress trees, and distant buildings. Natural light pours into the room, highlighting the stone sill and surrounding walls.
Home in Monticchiello
5 out of 5 average rating, 39 reviews

Lovely home to dream

NadinRating, 5 stars1 week ago
Sarah was in touch with us before arrival, recommended restaurants and inform us about the parking place, as you can't park inside the old town. the apartment was as in the pictures, beautiful view
Superhost
A spacious living area features a high wood-beamed ceiling, with a large table surrounded by wooden chairs. Comfortable sofas are arranged around a traditional fireplace. Warm lighting is provided by stylish lamps, creating a welcoming atmosphere. A rustic wooden cabinet adds character to the space.
Home in Montiano
4.81 out of 5 average rating, 16 reviews

Equus Domus in Maremma

JoannaRating, 5 stars6 months ago
Lovely place and very comfortable. Fiorenza is very friendly and responsive. We will definitely recommend to others and hopefully visit again ourselves.
Guest favorite
An ancient stone tower, partially covered in green vines, rises against a clear blue sky. The entrance, framed by a rustic arch, offers a glimpse of a small balcony above, with a wrought-iron railing. The surrounding buildings contribute to the historic character of the site.
Home in Manciano
4.94 out of 5 average rating, 18 reviews

La Civetta • iBorghi

AmélieRating, 5 stars1 month 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!

Private house rentals

Superhost
Stone pathways lead through the sturdy walls of Forte Filippo, with textures reflecting centuries of history. The fortress's robust ramparts rise above, framed by a bright blue sky with scattered clouds, offering a glimpse into the serene surroundings of Porto Ercole.
Home in Monte Argentario
4.97 out of 5 average rating, 76 reviews

Charming Spanish Fort 4 sleeps

NeilRating, 5 stars9 months ago
We were very impressed with the location. The old fort is very authentic and a great location overlooking the harbour. Don’t have a a lot of luggage as the steps from the moat up to the accommodation level are steep. Also, a large car may struggle to get through the automated door. We loved the unusual location and were able to walk down to the harbour and all the splendid restaurants. Takes about 15 minutes !
Top guest favorite
A rustic stone house is presented, featuring a sloped roof and wooden shutters. A set of stairs leads to the entryway, and a small porch area is visible. Surrounding greenery enhances the serene environment, offering a glimpse of the expansive valley beyond.
Home in Castell'Azzara
5 out of 5 average rating, 80 reviews

The Bandita dei Bovi

Jonathan S.Rating, 5 stars1 month ago
Deboras's home was so beautiful in the middle of Tuscany! The Tuscan views were amazing. Debora was so nice, showing me around the home. Thank you for our time. we can see ourselves spend some night in Debora's home.
Guest favorite
A light-colored sofa is positioned against a neutral wall, adorned with a large abstract artwork in muted tones. A small bookshelf with decorative items and potted plants adds a modern touch to the space, while a pillow with floral patterns enhances the sofa's comfort.
Home in Porto Santo Stefano
4.99 out of 5 average rating, 76 reviews

La Piazzetta Luxury Home

PontusRating, 5 stars1 month ago
Great location just a few steps from the harbor! Friendly and helpful host. Spacious apartment in a good condition. Perfect place for a stay in Porto Santo Stefano!
Guest favorite
A charming stone building features a textured exterior with a set of wooden shutters. A sturdy iron railing leads up to the entrance, with steps framed by potted plants. The clear blue sky and surrounding greenery enhance the inviting appearance of the home.
Home in Contignano
4.95 out of 5 average rating, 19 reviews

Noi 2 Vacanze in Fortino d 'Amore

MikeRating, 5 stars3 weeks 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.
Top guest favorite
The image displays a panoramic view of Montepulciano, showcasing an array of rustic buildings with terracotta roofs. The landscape features rolling hills in the background, and a green garden is visible in the foreground, enhancing the historic charm of the area.
Home in Montepulciano
4.95 out of 5 average rating, 19 reviews

Hortus Conclusus House

FionaRating, 5 stars1 week ago
Amazing place and would definitely be our number one place to stay when we return. Clean and spotless with luxuries like slippers are provided and some breakfast items too. Even a UK-Italy plug converter! Loved it! Thank you to Lucia, Luca and your mum! xx
Guest favorite
A spacious living area features a rustic stone fireplace, providing a focal point for the room. Comfortable seating arrangements are visible, including a patterned armchair and round ottoman. Large windows allow natural light to fill the space, enhancing the stone and wooden architectural details.
Home in Pitigliano
4.88 out of 5 average rating, 49 reviews

La Casa di Sissi in Pitigliano

KatieRating, 5 stars1 month ago
The home was nice and clean. Location was right in the heart of Pitigliano! We enjoyed our stay in Pitigliano, cute medieval town and very walk-able. Parking was a little bit of a challenge, we had to park outside of the city proper. But the steps where wroth it.
Top guest favorite
A welcoming dining area features a wooden table set with plates and glassware, accompanied by fresh fruit. A bouquet of flowers sits on an adjoining console, while a television displays scenic imagery against a warm, yellow wall illuminated by wall-mounted lighting.
Home in Pienza
5 out of 5 average rating, 52 reviews

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

ShirleyRating, 5 stars1 week ago
We loved our stay in this apartment. It was perfect for the three of us - clean and very well stocked for us with extra amenities!!!! We really appreciated that. We love Pienza, and very much enjoyed our stay here. Thank you!!!
Superhost
A terrace is presented with a yellow dining table set for four, adorned with plates and a vase of flowers. Two lounge chairs offer additional seating, while the expansive ocean view and coastal landscape enhance the inviting outdoor space.
Home in Porto Santo Stefano
4.88 out of 5 average rating, 58 reviews

Sassi Verdi Villa

NathanRating, 5 stars8 months ago
Beautiful accommodation, responsive host, very attentive and helpful, responds very quickly if needed. Quiet, peaceful environment, far from Porto Santo Stefano but compensated by a paradisiacal view. The very big assets are the solarium, the spectacular view from the terrace, the private beach 1km away. Despite our 2 hours late to arrival, we were very well received by Marco and his wife. They also agreed to come early when we left for organizational matters. We recommend 100% and will be back.

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