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House holiday rentals in Sassofortino

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Sassofortino

House rentals with a pool

Guest favourite
Home
4.93 out of 5 average rating, 46 reviews

Casa Fattore - Tuscan countryside house

MarciaRating, 5 stars2 weeks ago
We had a wonderful stay at this property which is a bit difficult to reach, but is more than worth the painstaking arrival. The fantastic location is simply breathtaking – expansive fields lined with cypresses and olive trees create a backdrop that looks like a Tuscany picture book. The hosts were extremely nice and charming. They provided us with great tips for excursions and activities in the area, which has enriched our stay. Particularly noteworthy is that our dog also felt very comfortable and we could thus enjoy relaxing time as a family. In summary, we can recommend this place to anyone who wants to experience the true beauty of Tuscany. A place to relax and enjoy – here we will be happy to come back.
Guest favourite
Home
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Superhost
Home
4.77 out of 5 average rating, 52 reviews

Tuscan Villa Poggetto Montalcino

SamRating, 5 stars7 months ago
Villa poggetto was a beautiful and quiet retreat. Our family used it as a base for seeing other parts of Tuscany and hired a car so it was perfect. It has basic amenities and the pool is in great condition. Only critique is the doors don’t lock well (not really a concern as the area is quiet) and as it is rural there are animals around such as mice and cute local cats. Gastone was a great host who allowed us to check in at 11pm when we were running late. He is very responsive and kind.
Superhost
Home
4.77 out of 5 average rating, 47 reviews

The Farmhouse in the heart of Maremma

GuusRating, 5 stars8 months ago
Ginevra was very friendly and forthcoming. Communication was smooth and prompt. Nice place, surely recommended!
Top guest favourite
Home
4.97 out of 5 average rating, 74 reviews

L'Olivo - detached villa with swimming pool

MartaRating, 5 stars7 months ago
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.
Superhost
Home
5 out of 5 average rating, 6 reviews

House with garden, pool and AC

ColinRating, 5 stars7 months ago
Spotlessly clean and tidy cottage and garden in a lovely, quiet and beautiful area. Fabulously clean and sparkly swimming pool. Eleanor, our host was friendly, helpful and very responsive, and made good suggestions for restaurants and places to visit. The food at Ripetta restaurant in Gradoli was excellent. Definitely a place we would be happy to return to.
Superhost
Home
5 out of 5 average rating, 3 reviews

Private villa with pool & AC, few km from Cortona!

MartinaRating, 5 stars6 days ago
The place is as pictured, in the Tuscan countryside. A slice of paradise where you can only hear the sounds of nature. The host and his son were super friendly and helpful in accommodating our requests. We had the opportunity to check in early and late check-out. The house is spacious and equipped with everything you need. The pool is great for relaxing and the outdoor table great for outdoor dining and grilling. We'll definitely be back
Top guest favourite
Home
5 out of 5 average rating, 7 reviews

Beautiful bright villa with view - Casa Luca

RafiRating, 5 stars1 month ago
We stayed at Mel's Casa Luca in March 2025 for over a week. Tucked away yet near medieval Campagnatico, it’s 5 minutes from the E78 to Grosseto/Siena, 15-20 minutes to Grosseto, and 30 minutes to the sea. Casa Luca, one of three stone farmhouses on what is essentially an olive farm, offers resort-like amenities which are shared with the guests of the other 2 houses: a trampoline, large pool, and ample walking space. Casa Luca is a single-storey house with two bedrooms with plenty of storage, comfy beds, an open-plan kitchen/dining/living area with Netflix, a big bathroom, and a well-equipped kitchen. Outside, there’s a private garden, terrace, BBQ. There is also a shared bakehouse with a pizza oven and huge dining table. We loved it and highly recommend it!

Weekly house rentals

Superhost
Home
4.77 out of 5 average rating, 31 reviews

Noi 2 Vacanze - Dario's House

LaurenceRating, 5 stars7 months ago
The views are beautiful. Peaceful neighborhood. However, the kitchen is missing several items for cooking.
Superhost
Home
4.78 out of 5 average rating, 9 reviews

Beautiful property between Siena and Arezzo

TimRating, 5 stars21 months ago
we had a very nice stay. The entire accommodation was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.
Superhost
Home
4.89 out of 5 average rating, 18 reviews

[15 min da Montepulciano] Villa Chiara

JoeRating, 5 stars7 months ago
Great location and the 2 full size bathrooms were nice!
Superhost
Home
4.86 out of 5 average rating, 116 reviews

The Sundial in Montefioralle

TatyanaRating, 5 stars6 months ago
Eugenio was a great host. His place is super authentic, located in the most charming medieval village with spectacular views. Everything in the house was to our satisfaction. Eugenio was super responsive and helpful with accomodating some extra requests that we had. We were travelling for work, filming a wedding at nearby castel. Location was great for us. The public parking is only about 100 meters from the house. We were teally happy with everything. Thank you Eugenio. P.S. There is an amazing restaurant with spectacular views right in the village. They only do lunches. But wow, It was such a great find. Everyrhing in that restaurant was made from their own produce, wine from their vineyard in the valley, olive oil from their trees, all vegetables from their garden. Different set menue every day. Really recommend it. It was delicious.
Guest favourite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars2 weeks ago
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again
Superhost
Home
4.92 out of 5 average rating, 12 reviews

Authentic tuscan barn 3 bedrooms 3 bathrooms

OliverRating, 5 stars9 months ago
The complex is in a larger clearing in the middle of the forest. Completely remote and quiet day or night. Pure relaxation. Well-maintained complex. Good kitchen equipment. Tastefully furnished apartment. Great pool. 14x7m. Perfect for a few laps or to romp. Location is perfect for excursions. Florence, Pisa, Siena each about 60 minutes away by car. In and around San Gimignano there are many restaurants with good Tuscan dishes. A reservation is often required if you like to move away from the tourist centers. Shopping facilities can be reached in 15 minutes. External garbage disposal at nearby collection points is a bit annoying. Laura took care of the personal key handover with us and speaks perfect German! All in all 5 stars! We will be happy to come back.
Guest favourite
Home
4.92 out of 5 average rating, 115 reviews

LECCIONE RESIDENCE

IsabelleRating, 5 stars1 month ago
Beatiful house with everything you need. The house was really clean, and it has all the amenities you need. The contact with Andrea was good. In the surroundings there is not much to do, but if you are looking for peace and quite, and you don't mind driving a bit for activities, this is the perfect place.
Superhost
Home
5 out of 5 average rating, 5 reviews

Farmhouse in Tuscany – Il Glicine

JérômeRating, 5 stars8 months ago
Available and helpful hosts, accommodation compliant with listings, a great base to discover the beauty of Tuscan: Siena, Pisa, Florence, Chianti, the coast, everything is accessible for 45-60 min drive.

Private house rentals

Home
4.75 out of 5 average rating, 4 reviews

La Madonnina x 17 pax by Interhome

DanielRating, 5 stars34 months ago
Great house, especially when several families/parties travel together, as there are a total of 3 apartments. House and surroundings very clean, contact via the key holder very straightforward. The caretaker was great, came every day and took great care of the pool and the surroundings - but didn't push up at all and mostly came to times when we weren't at the house. Too bad it doesn't have wifi.
Superhost
Home
5 out of 5 average rating, 5 reviews

Family House Baldana

RobertaRating, 5 stars8 months ago
It was our first time in Castiglione. Landlord (mother and daughter) very kind, welcoming and very helpful. Wonderful place, away from the chaos of the city but a short distance from the sea, surrounded by nature and peace. Spacious place, with everything you need inside and out with lounge chairs, umbrella, and table. We felt at home. Thanks again for everything. We will definitely be back.
Home
5 out of 5 average rating, 3 reviews

La Felcaia by Interhome

JenRating, 5 stars9 months ago
Luigi and Laura were the perfect host. The vegetables from Laura's family were very welcome. We also loved the dinner they cooked for us. We felt like part of the family. The villa was absolutely amazing. Stunning location, the pool was out of this world. We loved it so much we have already booked for next year!
Home
4.75 out of 5 average rating, 4 reviews

Villa Alba by Interhome

BernieRating, 5 stars31 months ago
Casa Alba was fantastic. We had a wonderful stay. We renewed our vows, at Casa Alba, to celebrate our 10 year wedding anniversary & it was a dream day 🤗 Luigi & his wife were there to welcome us & couldn't have been friendlier. My sister, brother in law & their toddler stayed the week with us & I can definitely say we loved it & would absolutely return 🙌 its very close to San Gimignano for everything you could need.
Home
5 out of 5 average rating, 10 reviews

Le Bonatte by Interhome

CarlRating, 5 stars7 months ago
Joy (the owner) is a joy! She is one of the best hosts we’ve had on this platform. Flexible checking, due to delayed flight. Rooms were bigger than anticipated and beautiful. Lovely rustic Tuscan charm of a property. Plenary of recommendations at the property for local restaurants and activities. Can’t recommend this property enough!
Home
5 out of 5 average rating, 4 reviews

Capanna di Sotto by Interhome.

AntjeRating, 5 stars8 months ago
we immediately felt comfortable 7 d enjoyed the stay very much. A ideal starting point for excursions.
Top guest favourite
Home
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars6 months ago
It was an absolute delight to stay at this gem of a property. We booked for 10 days and had a chance to enjoy and explore the surrounding areas. The house is spotless, comfortable, spacious, and fully equipped with modern appliances. So it has exceeded our expectations and would love to book it again in the future. Our host Alberto, is welcoming and very friendly, making the process of checking in and out quite seamless. My overall impression is 10/10.
Guest favourite
Home
4.88 out of 5 average rating, 16 reviews

Casa Ernesto - portion of farmhouse

ValentinaRating, 5 stars2 months ago
Two super welcoming and helpful sisters, ready to give useful directions and tips. The apartment is on the first floor of a historic farmhouse, a little gem out of traffic in the middle of the countryside. You can reach it along a dirt road (a little bumpy) with cypress trees (from the location that Chiara sends to the stanga immediately on the left!). The apartment is really very nice, clean, cozy and comfortable. There's everything you need, including the dishwasher, which is a plus. Comfortable beds, spacious rooms, super quiet area, at most you can hear vibes of some animals. It was a great experience!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Sassofortino
  6. House rentals