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Vacation 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 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 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!
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

AlessioRating, 5 stars3 weeks ago
Casa molto bella e funzionale, arredamenti e complementi d'arredo molto particolari. Terrazzo e camere con affaccio sul mare, si rimane senza parole. Un ringraziamento a Lavinia che ci ha seguito per l'intero soggiorno anche se non c'è stato nessun problema, tutto perfetto. Vacanza indelebile.
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 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 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, 15 reviews

Fattoria Tolomei Casa di Pietra

AnneRating, 5 stars5 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
A private pool is set within a landscaped garden, featuring a unique heart shape. Sun loungers are positioned beside the pool, surrounded by well-maintained greenery. The area is enclosed by hedges, providing a sense of privacy and tranquility.
Home in Sant'Antonio
4.82 out of 5 average rating, 28 reviews

House with private pool

RonaldRating, 5 stars10 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 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 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
An outdoor area features a swimming pool surrounded by lounge chairs and shaded by an umbrella. A vibrant pink inflatable floats in the pool, with a children's play structure nearby. A small table and chairs provide a space for relaxation within the lush greenery.
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
An ancient farmhouse is surrounded by lush greenery and olive groves, with a glimpse of a tranquil salt-water pool in the background. The warm brick façade is complemented by wooden beams and a charming patio, inviting relaxation in a natural setting.
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 !

Condo rentals with a pool

Superhost
An outdoor swimming pool is featured, surrounded by lush greenery and trees. Poolside lounge chairs and an umbrella provide relaxation options. Soft lighting creates a serene atmosphere as dusk falls over the charming countryside, with a rustic building visible in the background.
Condo in Montepulciano
4.87 out of 5 average rating, 39 reviews

Appartamento Girasole

GianmarcoRating, 5 stars3 weeks ago
Amazing place, staff provides great service whenever needed
Superhost
A bright living area features large windows providing views of the sea. A comfortable sofa is positioned beside a modern coffee table. A dining table is visible, complemented by a light fixture above. A fireplace adds character to the inviting space.
Condo in Porto Santo Stefano
5 out of 5 average rating, 4 reviews

Amazing Calamoresca

BarbaraRating, 5 stars21 months ago
Casa luminosa e accogliente esattamente come da fotografie e descrizione. Cucina funzionale e spazi ampi e ben disposti. Bagni puliti e moderni. Terrazza con vista mare e panorami fantastici ad ogni ora del giorno e della notte, ne eravamo ipnotizzati! Contesto tranquillo e rilassante all'interno del consorzio Cala Moresca che conoscevamo già ma che ha saputo stupirci di nuovo per gli spazi comuni curatissimi e pulitissimi per la strepitosa piscina incastonata nelle rocce con annessa discesa al mare cristallino. Top! Per finire proprietaria deliziosa e molto disponibile che ci ha fatto sentire come a casa. Assolutamente da ripetere.
Guest favorite
An aerial view captures the property surrounded by lush greenery and fields, featuring a central swimming pool with a circular layout. The inviting outdoor area is complemented by well-maintained hedges and cypress trees, while rustic buildings provide accommodation nearby.
Condo in Grosseto
4.83 out of 5 average rating, 30 reviews

Il Granaio apartment Il Fienile with pool

MartinaRating, 5 stars11 months ago
Abbiamo soggiornato una settimana in una delle casette del granaio. La struttura è immersa nella campagna della Maremma dove regnano la pace e i suoni della natura. A pochi minuti di distanza negozi di verdura, prodotti tipici e supermercati. Le spiaggia vicine sono comodamente raggiungibili in pochi minuti di auto e adatte alle famiglie. Gli host ci hanno consigliato spiagge, ristoranti e attività da fare nei pressi della struttura. La casetta è arredata semplicemente ma tutto è perfettamente funzionante e funzionale, il giardinetto di cui dispone ogni appartamento è delizioso, fresco e pieno di fiori. Per noi è stata una soluzione ideale per poter esplorare la zona e avere la privacy e la tranquillità che cercavamo per le nostre vacanze.
Guest favorite
A saltwater swimming pool is set within a paved sun terrace, surrounded by lounge chairs and shaded by a wooden gazebo. Lush greenery and a brick wall create a serene backdrop, while the farmhouse structure is visible in the distance under clear blue skies.
Condo in Buonconvento
4.93 out of 5 average rating, 28 reviews

Relax between Siena and Valdorcia

ManonRating, 5 stars1 week ago
Logement très agréable, spacieux, bien équipé et confortable. La terrasse et la piscine sont super et permettent de bien profiter du magnifique paysage du Val d’Orcia. C’est facile de se stationner. La route passe devant le logement mais nous étions quand même très au calme et nous nous sommes vraiment sentis en pleine nature. Je recommande sans hésiter pour un doux séjour en pleine nature milieu du Val d’Orcia !
Superhost
A natural rock-style swimming pool is visible, surrounded by lush greenery and palm trees. A rustic house with a yellow exterior is positioned nearby, framed by the vibrant landscape. The clear blue water of the pool reflects the sunny sky, enhancing the serene outdoor setting.
Condo in Valpiana
4.79 out of 5 average rating, 14 reviews

Apartment + pool Maremma Tuscany

DavideRating, 5 stars9 months ago
Soggiornare all'agriturismo Valentini è come un'esperienza in famiglia. Chiara, Luca e Giovanni ci hanno fatto sentire subito a casa, con un caloroso benvenuto ricevuto al nostro arrivo e con tanta disponibilità, simpatia, affabilità e attenzione durante tutta la vacanza, ma senza alcuna invadenza. La tenuta è un posto dove rigenerarsi, immersi nella natura e nelle distese sterminate di vigneti e ulivi, che la famiglia Valentini cura con tanto amore. L'appartamento è provvisto di tutti i comfort e di uno spazio esterno intimo per godersi appieno il soggiorno, con aree condivise in cui i villeggianti hanno il massimo rispetto reciproco. Oltre all'esperienza naturalistica, la piscina è uno dei pezzi forti di cui godere nelle giornate calde. L'agriturismo, infine, è in una posizione strategica che dà accesso alle maggiori attrazioni locali (dal mare alla collina, dalle acque cristalline alle cittadine medievali) a soli pochi km di auto.È stata l'esperienza che cercavamo e che consigliamo.
Guest favorite
The image showcases a private swimming pool surrounded by greenery and stone walls. The water is clear and inviting, reflecting the sky above. A shade umbrella and lounge chairs are positioned nearby for relaxation, while the mountains create a scenic backdrop.
Condo in Bagnoli, Arcidosso
4.79 out of 5 average rating, 58 reviews

House in the small village with private pool

MaraRating, 5 stars3 days ago
L’alloggio di Riccardo rispondeva precisamente a foto e aspettative, tutto pulitissimo. Un po scomodo accedervi ma una volta lì il quartiere era super bello, accoglienti anche i vicini, la posizione perfetta per girare la zona della Val d’Orcia, il monte Amiata e i colli spettacolari, la piscina poi era una chicca per il tardo pomeriggio sia per grandi che per piccini. L’host super disponibile ma discreto. Grazie Riccardo!
Top guest favorite
A spacious bedroom is highlighted by a decorative sunburst headboard. Soft lighting from two bedside lamps creates a gentle glow. A mirror is mounted on one wall, and a coat rack stands nearby. The tiled floor and exposed wooden beams contribute to the overall design.
Condo in Massa Marittima
5 out of 5 average rating, 44 reviews

Podere Casanovola appartamento Il Sole

CorinnaRating, 5 stars3 weeks ago
Der Aufenthalt war wirklich sehr erholsam. Der Garten ist groß und ruhig, da kann man gut entspannen und wenn’s zu heiss wird in den Pool springen. Maria und Rodolfo sind sehr nette Gastgeber und haben uns super empfangen. Wer die Ruhe sucht ist hier richtig. Mit dem Auto erreicht man auch gut das Meer oder schöne Städte.
Top guest favorite
A serene outdoor pool is surrounded by lush greenery, with sun umbrellas positioned around the edges. Rolling hills and a clear sky provide a scenic backdrop, offering a quiet and inviting atmosphere for relaxation.
Condo in Montieri
5 out of 5 average rating, 48 reviews

PodereCupiano "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.

Home rentals with a private pool

An aerial view of a spacious countryside property surrounded by rolling green fields and olive trees. The kidney-shaped swimming pool is visible among tall trees, with a parking area and a few cars nearby. The house features a traditional design, complemented by the serene landscape.
Home in Castel del Piano
5 out of 5 average rating, 3 reviews

Il Cipresso by Interhome

StefanieRating, 5 stars3 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.
A rectangular swimming pool is surrounded by a stone patio and several lounge chairs. Lush greenery and trees are visible in the background under a clear blue sky.
Home in Lago di Bolsena
4.32 out of 5 average rating, 19 reviews

Casale Vitello by Interhome

ThibaultRating, 5 stars8 months ago
Nous sommes très contents, de ce séjour et nous avons passé un très bon moment avec de très bon échanges.
Home in Castiglione d'Orcia
4.67 out of 5 average rating, 30 reviews

Casa Frati by Interhome

JoJoRating, 5 stars2 weeks 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
4.67 out of 5 average rating, 6 reviews

Meridiana by Interhome

DennisRating, 5 stars1 week ago
Wir hatten eine wunderbare Zeit in der Unterkunft. Das Haus ist noch um einiges schöner als es sowieso auf den Fotos aussieht. Die Gegend ist auch wunderschön. Es war zudem immer eine Person vor Ort sofort erreichbar und sehr hilfsbereit und flexibel. Das Haus war sauber und hatte alles zu bieten. Wir können diese Unterkunft nur weiterempfehlen. Danke für den tollen Urlaub!
Home in Radicofani
4.86 out of 5 average rating, 7 reviews

Val d'Orcia by Interhome

NiccoloRating, 5 stars18 months ago
Posto perfetto, Podere accogliente, perfetto per rilassarsi anche in inverno.
A serene outdoor area features a rectangular swimming pool surrounded by paved terrace and sun loungers. Shade is provided by umbrellas near the pool. Lush greenery and trees line the property, with distant hills visible under a clear blue sky.
Home in Poggioferro

Villa al Sole by Interhome

MartinRating, 5 stars9 months ago
Das Haus hat in jeder Hinsicht der Beschreibung entsprochen. Es war genau wie auf den Bildern. Der Vermieter war sehr nett. Er war immer erreichbar und hat sich um alles gekümmert. Alles top 👍👍👍👍 5 Sterne ⭐️⭐️⭐️⭐️⭐️
Home in Cinigiano
4.38 out of 5 average rating, 8 reviews

Le Calle by Interhome

Ann-KathrinRating, 5 stars20 months ago
Die Anreise ist abenteuerlich. Dort angekommen findet man aber einen tollen Fleck Erde, denn das Haus von Savina & Riccardo ist eine echte Perle. Toller Ausblick, ruhig und privat. Am besten man packt sich ein bisschen Proviant ein, kauft vielleicht noch einen guten Wein & Käse vom eigenen Biohof der beiden und lässt es sich gut gehen. Savina ist eine tolle Gastgeberin und hilft gerne bei allen Fragen via WApp. Im Ort gibt es einen kleinen Markt, der das Nötigste hat. Es lohnt sich aber, noch mal in einem größeren Supermarkt Halt zu machen. Wer seinem Auto die Fahrt zum Ferienhaus nicht zutraut, der wird auch zu dem ca. 2 km entfernten Anwesen gebracht. Die erste Ab- und Auffahrt waren wild, aber man gewöhnt sich dran und unser Mercedes Vito hat’s gepackt. Highlight war definitiv das Wein Tasting und die tollen Produkte ihres Biohofs :)

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