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Holiday rentals with a pool in Province of Grosseto

Find and book unique homes with a pool on Airbnb

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Popular amenities for Province of Grosseto rentals with a pool

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 stars2 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!
Guest favourite
Home in Catabbio
4.89 out of 5 average rating, 159 reviews

Country house La Meria

AlexRating, 5 stars1 month ago
If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!
Guest favourite
Home in Grosseto
5 out of 5 average rating, 14 reviews

Tolomei Farmhouse in Stone

LisaRating, 5 stars5 months ago
Beautiful vacation home with fantastic views and warm hosts. Thanks for everything!
Superhost
Home in Sant'Antonio
4.82 out of 5 average rating, 28 reviews

House with private pool

RonaldRating, 5 stars9 months ago
We enjoyed our stay at Maria Teresa's place. The garden is really fantastic and nicely maintained. You can sit in different places, there is even an outdoor kitchen with refrigerator ,freezer and gas fork. The pool is super clean and is cleaned every morning. The house itself is also very nice, cool and equipped with every comfort. The surroundings are very quiet and for nature lovers plenty to spot wildlife within a 2-minute walk. We spotted deer, pigs, foxes and even a wolf. Really great! The poolside paradise sign is not there for nothing, it is really a paradise! We definitely recommend it and if we are in the area again we will definitely come back! Maria Teresa thank you so much for everything!
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!
Superhost
Home in Sorano
4.8 out of 5 average rating, 128 reviews

Lovely home in villa with garden and pool

JoshRating, 5 stars2 weeks ago
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
Superhost
Home in Scansano
4.84 out of 5 average rating, 62 reviews

Il Casaletto in the heart of the 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 !
Guest favourite
Home in Poggi del Sasso
4.92 out of 5 average rating, 117 reviews

LECCIONE RESIDENCE

RachelleRating, 5 stars2 weeks ago
We had a truly amazing stay at Andrea’s home. We were welcomed by his parents with a home made cake, jam and wine from a local winery. When planning the trip with our parents and 12 month old, we wanted somewhere we could enjoy amenities of the home, but also be close enough to day trip to different locations in Tuscany. This was the perfect spot! We enjoyed the pool and hot tub as well as day trips to Florence, Grosseto and Siena. Andrea provided amazing recommendations on local places to visit, as well as advising that taking the bus to Florence from Paganico. We couldn’t have asked for a better location and host for our extended family trip to Tuscany!

Condo rentals with a pool

Superhost
Condo in Montepulciano
4.87 out of 5 average rating, 39 reviews

Girasole Apartment

GianmarcoRating, 5 stars2 weeks ago
Amazing place, staff provides great service whenever needed
Superhost
Condo in Porto Santo Stefano
5 out of 5 average rating, 4 reviews

Amazing Calamoresca

BarbaraRating, 5 stars21 months ago
Bright and cozy house exactly as shown in the photographs and description. Functional kitchen and spacious and well-disposed spaces. Clean and modern bathrooms. Terrace with sea view and fantastic views at every hour of the day and night, we were mesmerized! Quiet and relaxing setting within the Cala Moresca consortium that we already knew but was able to amaze us again with the well-kept and very clean common spaces for the amazing pool set in the rocks with an attached descent to the crystal clear sea. Top! Finally, a delightful and very helpful owner who made us feel at home. Absolutely repeatable.
Guest favourite
Condo in Grosseto
4.83 out of 5 average rating, 30 reviews

Il Granaio apartment Il Fienile with pool.

MartinaRating, 5 stars11 months ago
We stayed a week in one of the barn houses. The property is immersed in the Maremma countryside where the peace and sounds of nature reign. A few minutes away from vegetable shops, typical products and supermarkets. The nearby beaches are easily accessible in a few minutes by car and suitable for families. Hosts have recommended beaches, restaurants, and things to do near the property. The house is simply furnished but everything is perfectly functional and functional, the garden that each apartment has is delicious, fresh and full of flowers. For us it was an ideal solution to be able to explore the area and have the privacy and tranquility we were looking for for our holidays.
Guest favourite
Condo in Buonconvento
4.93 out of 5 average rating, 28 reviews

Relax between Siena and Valdorcia

CalvinRating, 5 stars1 week ago
I stayed at this place for 4 nights with my partner at the beginning of June 2025. It was so homely, very tidy and clean, with lots of amenities and the host was very welcoming. The views were incredible. We had a car which made visiting other places super convenient. We definitely recommend and would love to come back one day!
Guest favourite
Condo in Bagnoli, Arcidosso
4.79 out of 5 average rating, 57 reviews

House in the small village with private pool

ChrisRating, 5 stars4 weeks ago
Quaint and cozy countryside cottage in a small welcoming village for an authentic experience. An opportunity to slow down and explore the beautiful landscape. Responsive host with a well stocked kitchen. Grocery store nearby. Walking trails everywhere and hot springs accessible with a car.
Top Guest favourite
Condo in Massa Marittima
5 out of 5 average rating, 44 reviews

Podere Casanovola, Il Sole apartment

SarahRating, 5 stars5 days ago
We had a great time staying with Rodolfo and Maria on their beautiful farm. Thank you so much!
Top Guest favourite
Condo in Montieri
5 out of 5 average rating, 48 reviews

Podere Cupiano "La Costa"

LucyRating, 5 stars1 week ago
Francesco is an excellent host. Podere Cupiano is a fantastic estate. The views are to die for. Sopratutto, the pool is amazing. Montieri is a super cute and friendly town nearby with great restaurants. You should also visit the restaurant at VIN Hotel, a ten minute walk away.
Superhost
Condo in Pienza
4.82 out of 5 average rating, 17 reviews

Family Country House in Val d'Orcia, Pienza

BronwenRating, 5 stars9 months ago
This place is a dream! So beautiful with friendly hosts! So peaceful and a great place to relax. Location is great for a short drive to many attractions.

Home rentals with a private pool

Home in Castel del Piano
5 out of 5 average rating, 3 reviews

Il Cipresso by Interhome

StefanieRating, 5 stars2 weeks ago
The house was amazing, especially the area and the views. Sitting outside and using the pool in this beautiful surrounding were absolutely fantastic. It's a very wie and lovely place with a very nice pizza oven and barbecue outside. The owner are very nice and the communication was really good. We would really like to come back. Thank you for everything and also for the nice olive oil!
Home in Castelnuovo di Val di Cecina
4.67 out of 5 average rating, 3 reviews

Pino di Sopra, by Interhome

MarthaRating, 5 stars24 months ago
Agrotourismo Pino di Sopra is a beautiful set of rooms in a peaceful part of Tuscany off the beaten track. The house is set up as two apartments and two double rooms, so perfect for two families sharing or a group of friends where you can all have your own space. The pool is large and suitable for kids and adults alike. I would highly recommend staying here. Our only negative was that the host told us we had to communicate off platform with the key holders (owners) which I was uncomfortable with. I had trouble getting in touch with the key holders and the hosts did not respond to my messages for assistance or offer any support with this. Once I made contact via SMS the owners were very helpful and responsive. It there was undue stress in the lead up to our trip.
Home in Lago di Bolsena
4.32 out of 5 average rating, 19 reviews

Casale Vitello by Interhome

ThibaultRating, 5 stars8 months ago
We are very happy with this stay and we had a lovely time with very good exchanges.
Home in Castiglione d'Orcia
4.67 out of 5 average rating, 30 reviews

Casa Frati by Interhome

JoJoRating, 5 stars1 week ago
Overall the location and charm of the property were stunning. Spacious bedrooms and living areas (beware uneven flooring, to be expected in an old farmhouse, my elderly father struggled). NOTE: we have not been asked for a cash deposit with Airbnb before and were surprised when a man came about 3 hours after we arrived to collect €400 cash. He spoke no English and used his phone to call someone who could speak to me. The host had not said he would be coming, or who he was. I contacted Airbnb support who said I could pay through the resolution centre. As others mentioned, there were no oil, salt, pepper etc, although a few dishwasher tablets. The jacuzzi and sauna work with tokens for €8 each. Didn’t use so not sure how long you get. BUT, this is a stunning property with unbeatable views in the heart of Tuscany, tucked away on a hillside down a gravel track. Would definitely book again. Pool is pristine, towels spotless, beds comfortable.
Home in Roccalbegna
4.6 out of 5 average rating, 5 reviews

Meridiana by Interhome

DennisRating, 5 stars5 days ago
We had a wonderful time staying at the place. The house is even more beautiful than it looks in the photos. The area is beautiful too. There was also always a person on site immediately available and very helpful and flexible. The house was clean and had everything to offer. We highly recommend this place. Thank you for a great holiday!
Home in Radicofani
4.86 out of 5 average rating, 7 reviews

Val d'Orcia by Interhome

AmandaRating, 5 stars21 months ago
Awesome property! Super responsive host!
Home in Poggioferro

Villa al Sole by Interhome

MartinRating, 5 stars9 months ago
The house corresponded to the description in every way. It was just like the pictures. The landlord was very nice. He was always available and took care of everything. Everything top 👍👍👍👍 5 stars ⭐️⭐️⭐️⭐️⭐️
Home in Roccastrada
4.86 out of 5 average rating, 14 reviews

Casale Ulisse by Interhome

RasmusRating, 5 stars1 month ago
Alessandra’s place is great specially for nature lovers. Cute little town nearby (walking distance) with nice restaurant and gelateria. Host was friendly and answered fast.

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