
Condo vacation rentals in Province of Grosseto
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Top-rated condo rentals in Province of Grosseto
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Popular amenities for Province of Grosseto condo rentals
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IAZ's home
everything was perfect, it felt like home

Amazing Tuscan beachfront apartment
Very special location at the sea. House is beautiful. We realy enjoyed.

a.d. 1237
What an incredible stay!! 10/10. We traveled all over Tuscany for 2 weeks and this stay ranks right up there at the top. From the communication and ease of getting to the apartment to the beautiful old history of the building and town. Just wow! Book it:) We loved the town and her people🫶🏼 The apartment was comfortable in every way. Grazie mille, Heather & Beth

The walnut tree view, Montepulciano
Luca is an amazing host! He is super friendly and responsive. His apartment is in a very good and peaceful place. The view is just amazing. Highly recommended!

Cozy apartment in Maremma, Grosseto, Tuscany
Perfect home and really helpful hosts!

[A few steps from the beach] parking and A/C
We had a most relaxing stay at Chiara’s place. Right by the water. The view was amazing from the deck. We were there off season so many restaurants were closed, but that was fine for us. Walking the quieter boardwalk and beach was what our souls needed. Would definitely recommend.

Bellavista Casetta
The host Claudia is very kind, very helpful and very nice! Strategic accommodation in the center of Scansano, very clean and comfortable! If I come back to this area, I will not hesitate to call Mrs. Claudia again.

New two-room apartment within walking distance of the center and the sea
Great very modern, clean and newly renovated apartment. The location is very central and you can walk to everything in Castiglione. We particularly liked the two air conditioners in the living room and bedroom, which always kept the apartment nice and cool. The kitchen could have been a little better equipped as there are not so many dishes, spices, or an espresso cooker (only capsule coffee maker). Of course, this is also due to the fact that the apartment would not be booked as often yet. Although the apartment is located in a quiet side street, you can still hear a lot of the main street and the restaurants despite the closed windows. But if you don't have a light sleep, that won't bother you. Elsa was a very kind and helpful host. We were also particularly pleased with their tips and recommendations on the restaurants and bars. We would book the accommodation again at any time.
Pet-friendly condo rentals

Surrounded by pine forest, 300 meters from the sea
We stayed in this property, chosen a bit randomly among many, and I must say that never was a better choice. Roberta immediately proved to be helpful, friendly, and with her demeanor, she made us feel immediately at ease. The apartment is really nice, spacious, bright, brand new and fantastically maintained, the sea is really a few steps away with an immense and very well maintained beach, the town offers the essentials but in the surroundings there is a lot to do and see. A mini vacation that will remain in our hearts, as well as Roberta, 🥰 with whom we are sure we will hear from soon to organize a longer vacation. So I recommend everyone to try the location in order to get to know the place... You won't regret it, but above all, Roberta...

Casa Medina, overlooking the Orbetello Lagoon
Good location close to the city. Convenient parking and public charging for EVs nearby. Also close to several beaches to explore by car or bike.

Casa Gioia
Great place, very cosy with the Tuscan vibes. No issue checking in, Nicolo is a great communicator. Amazing views of rolling Tuscany hills only minutes from the doorstep, which is right near the centre of Pienza!

Casa Marina - Studio apartment with sea view
Located 3 minutes from the sea, a short walk from downtown and in a nice and quiet neighborhood. We made a nice and available host. For us who come 2-3 times in Follonica, it will be a fixed stop

House in the small village with private pool
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.

Sea House
I recently had the pleasure of staying at Consuelo's Airbnb apartment near the sea in Castiglione de la Pescaia, and it was an exceptional experience from start to finish. Consuelo is an outstanding host—both incredibly helpful and remarkably responsive. From the moment I booked, she ensured smooth communication, promptly addressing any queries I had with warmth and efficiency. Her attention to detail and dedication to guest comfort made our stay truly effortless. The apartment itself was spotless, well-equipped, and perfectly situated for easy access to the beautiful coastline. I wholeheartedly recommend Consuelo's Airbnb to anyone looking for a delightful seaside retreat. Her hospitality truly elevates the experience, making it feel like a home away from home.

Podere Cupiano "La Costa"
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.

Martina's House with a Sea View - Private Parking
We spent a beautiful week in the beautiful apartment of Rosà, the perfect host responded quickly and attentively. The panoramic view of the apartment takes your breath away... everything is perfectly clean, elegant furnishings and attention to the small things. You feel at home. Parking near the house is convenient to use. Highly recommended, we will definitely be back.
Condo rentals with a pool

Stylish Italian Apartment w/ Pool, Near Beach!
We had a wonderful time in the apartment Mirto. Everything was thought of, we were warmly welcomed, there was a huge fruit bowl and wine. The amenities were especially great for families. Even a laundry basket was there. The outdoor area was indescribably beautiful. So much space. So much nature. This tranquility. Heavenly. We slept wonderfully. Beds are very comfortable. There are plenty of cabinets. The furnishings of all rooms are incredibly tasteful. We felt incredibly comfortable. Thank you for the wonderful time ♥️ We recommend a trip to the magical mountain village of Pitigliano, about 1 hour away.

Girasole Apartment
Amazing place, staff provides great service whenever needed

Amazing Calamoresca
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.

Il Granaio apartment Il Fienile with pool.
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.

Relax between Siena and Valdorcia
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!

Apartment + pool Maremma Tuscany
Staying at the Valentini farm is like a family experience. Chiara, Luca and Giovanni immediately made us feel at home, with a warm welcome received upon our arrival and with so much availability, friendliness, affability and attention throughout the holiday, but without any intrusion. The estate is a place to regenerate, immersed in nature and in the endless expanses of vineyards and olive trees, which the Valentini family takes care of with so much love. The apartment is equipped with all comforts and an intimate outdoor space to fully enjoy the stay, with shared areas where vacationers have the utmost mutual respect. In addition to the naturalistic experience, the pool is one of the highlights to enjoy on hot days. Finally, the farm is in a strategic position that gives access to the main local attractions (from the sea to the hill, from the crystal clear waters to the medieval towns) just a few kilometers by car. It was the experience we were looking for and what we recommend.

Podere Casanovola, Il Sole apartment
We stayed with Maria and Rodolfo for four nights and felt very, very comfortable. The beautiful house is off the road in idyllic countryside, surrounded by a park-like garden; a Shangri-La in the Maremma. The house is conveniently located for exploring the sights of the surrounding area. Maria and Rodolfo are the friendliest, most considerate and pleasant hosts you could imagine. Thank you for everything!!

Sleep among the vineyards of Maremma
We had a great weekend with friends. Beautiful location, home with everything you need to enjoy the indoor and outdoor common spaces. Very kind and helpful host. Don't hesitate to ask for tips about the area, the host's tips were great dinner and a visit to beautiful Pitigliano! I plan to come back if I go back to the area!
Destinations to explore
- Rentals with outdoor seating Province of Grosseto
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- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Giannutri
- Feniglia
- Gulf of Baratti
- Cala Violina
- Kite Beach Fiumara
- Marina di Grosseto beach
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Avignonesi Winery Fattoria Le Capezzine
- Spiaggia Marina di Cecina
- Cala Di Forno
- Santa Maria della Scala
- Spiaggia Di Barbarossa
- CavallinoMatto
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Zuccale
- Tenuta Le Velette
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Pubblico Palace
- Spiaggia Di Sottobomba
- Spiaggia della Padulella
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