
House holiday rentals in Sassofortino
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Top-rated house rentals in Sassofortino
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House rentals with a pool

Family Forest - Pool in the Crete Senesi
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!

Charming estate with views
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.

Podere Tignano, 4-bedroom villa in the Chianti!
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Bel Casale with sea view and the mediaeval village
Staying at Paola and Nino’s place was one of the highlights of our trip. The house is even more beautiful than the photos, with every detail thoughtfully considered and a setting that truly captures the essence of Tuscan magic. It’s incredibly peaceful, with sweeping views and a real sense of privacy, yet close enough to explore charming villages and beaches. The house is well-equipped and very comfortable, with excellent air conditioning in the bedrooms, a real plus during the summer heat. Paola and Nino were the most gracious hosts, warm, welcoming, and always available if we needed anything, yet also giving us plenty of space. Their three sweet labradors were a lovely bonus! We truly didn’t want to leave and would return in a heartbeat.

Casa di Lyndall - Entire house with exclusive pool
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

Collina Power
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!

Gaiole in Chianti Poggio Casabianca
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!

House in the Maremma hills
A stunning property in the Tuscan hills, with the small village of Ribolla nearby with local amenities. Friendly welcoming hosts, set on a winery. Facilities second to none, absolutely gorgeous swimming pool and view across the value. Will definitely be returning. Take your iPad if you need to watch any tv! Bellissimo!
Weekly house rentals

Hidden gem in Tuscany
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.

Cozy country house Podere Scorno with pool
Very local experience ~ It's great to be able to experience local life!It's like going back to the environment and house of my childhood. It's very comfortable!The host is also very nice!!!I gave a lot of recommendations!!!Thank you very much!!!

Casa Ora d"Oro - Panoramic Views
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!

Villa in Maremma
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!

La Casetta
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.

Tosco Suite "Solis"
Location was perfect and close to fun things to do. The host was very responsive and friendly. 10/10 recommend staying here. Everything was very cleaned and beautiful.

Delightful loft surrounded by greenery with garden
It was a more than pleasant stay. Ezio and Angela's home is a small paradise surrounded by nature. We were welcomed as family. Communication was great, easy and good advice. I really appreciated the great flexibility in check-in and check-out that made us independent. Everything really great! We'll definitely be back! Very convenient to reach the thermal springs of Petriolo: just under half an hour by car in the middle of the countryside.

L'Uva Fragolina. House, Garden, Panoramic View
A Tuscan dream. Some days I had to pinch myself to realize that I wasn't in a movie. My girlfriend and I had a wonderful time in the region and also in the house. It was clean and tidy. The kitchen was unique and we also enjoyed grilling outside. We simply enjoyed it and felt at home. Finally, relaxation and tranquility, which you rarely experience. Thank you for your trust in this wonderful piece of Tuscany. A must-see for all those seeking peace and quiet or people who really want to experience what Tuscan flair means. We will be happy to come back!
Private house rentals

Wonderful country house
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

Casa Elicriso
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

Casa San Ripa: Relax Oasis with Private Pool
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!

Domus Antiqua
We loved staying in this beautiful home in Montalcino. It was even more beautiful and unique than the pictures! My family of five loved staying here- lots of space for everyone and it was fun to be right in the 500 year old town. We especially love having coffee and wine on the balcony.

Countryhometuscany - House with Garden -
Beautiful property with warm, welcoming hosts. The bed was exceptionally comfortable, and everything is tastefully decorated The kitchen is fully equipped, perfect for cooking meals at home. The pool was a great temperature, immaculately clean, and came with stunning views of the surrounding countryside. The entire setting is peaceful and relaxing, yet only a 35-minute drive to Siena and 50 minutes to Florence. We especially loved watching the sunset at the nearby five-star Belmond hotel. We went for drinks at 7pm, enjoyed live music, and were surrounded by the heavenly scent of jasmine. There is no air conditioning but the fans were absolutely fine! Another highlight was La Speranza, a gorgeous deli serving excellent coffee, pastries, cheese, and wine. They kindly spoke English when we got stuck and made us feel so welcome.

La Bandita Dependance
We picked the location based on (very last minute) availability Airbnb’s. Both the city and Airbnb did not disappoint. The house was very chill and provided us with plenty of privacy and met all our needs. Azzurra was very helpful. And the city (with help of Azzuras tips) provided us with the relaxation we were looking for. Wish we booked a longer stay. Only recommendation for future guests, a car is required to navigate through the area.

La Moraiola - Characteristic Tuscan barn
I took this trip with my sister to San Gimignano and it was absolutely incredible! The views from Egizia’s house were just stunning and breathtaking! From the beginning Egizia was very easy to get into contact with about any questions that I had. She gave wonderful recommendations and booked everything for me! We went to a winery that she had suggested and it was great! The Pilates instructor Giulia was also amazing! And with the hills as our scenery it was such a cool and incredible experience! My sister and I had so much fun! This was an unforgettable trip! We’ll definitely have to come back again!

Chianti House Stunning view 20 min. from Florence
What a place! An absolutely perfect little hideaway in an absolutely gorgeous location. This charming abode has exactly what you need to completely escape and soak in the stunning surroundings of the Tuscan landscape. Even though it rained quite a bit of our visit, sitting on the veranda overlooking the pool and rolling hills nice and dry under the tent was magical - the lush view could never get old! The stone space is as quiet and cozy as can be - comfortable bed and couch, very functional kitchen, nice bathroom. Pretty antiques make the space homey. My husband even jumped in the very cold pool in the rain and now we want to come back in the summer sun to enjoy it more. Tommaso was incredibly sweet and offered recommendations and walked us through the whole place upon check in - and he was kind and responsive the whole time. Really can’t recommend this experience enough!
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- Elba
- Giglio Island
- 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 di Marina Di Campo
- Cavallino Matto
- Spiaggia Marina di Cecina
- Cala Di Forno
- Santa Maria della Scala
- Casa Barthel
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Di Barbarossa
- Spiaggia Zuccale
- CavallinoMatto
- Cala del Leone
- Spiaggia della Padulella
- Spiaggia di Cavo
- Pubblico Palace