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House vacation rentals in Sassofortino

Find and book unique houses on Airbnb

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Popular amenities for Sassofortino house rentals

House rentals with a pool

Guest favorite
Home in Arezzo
4.9 out of 5 average rating, 167 reviews

Italian Interior

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Guest favorite
Home in Asciano
4.94 out of 5 average rating, 36 reviews

Family Forest - Pool in the Crete Senesi

JánRating, 5 stars1 week ago
The apartment really enchanted us, the rooms are nice, clean with air conditioning, stylish, in the living room a large TV, kitchen with everything that should be here. The "resort" itself was on a hill with beautiful views, a huge garden, a swimming pool, all stylish Tuscan, the surroundings are beautiful, peace, quiet, peace, everything you need here you will find. As the Italians say, it's "Tutto bene" here
Guest favorite
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Monte San Savino
5 out of 5 average rating, 33 reviews

Beautiful villa with pool in secluded location

NeilRating, 5 stars8 months ago
We had a lovely stay here. The location was perfect—exactly what we were looking for. Peaceful, quiet, surrounded by nature, with classic rustic, yet elegant furnishings. The villa is gorgeous with attention to design & detail. For 6 women, it was perfect for us each to have our own bedroom and space to relax. Each room had its own unique view and touch. There are also plenty of common spaces throughout the house for connecting together. The kitchen is large enough and fully equipped for plenty of great meals to be prepared and enjoyed together. The dining room is nice to enjoy a more elegant meal. The outdoor spaces are beautiful. We used the outdoor terrace for watching the sunset, enjoying brunch, and making pizzas. The washing machine and dryer are easy to use. The pool area is beautiful and there are plenty of outdoor spaces to go for a walk and enjoy the surrounding nature. The hospitality was unmatched from Tristan & Angela. I will absolutely book again and hope to return soon!
Superhost
Home in Buonconvento
4.88 out of 5 average rating, 17 reviews

Il Fienile - Pool Villa with 4 Bdrs and Sauna

SadieRating, 5 stars5 days ago
This place is a dream! Everything is stunning. I loved every room and every view. Everything is thoughtfully put together with comforts like an ice machine and AC on when you arrive. The staff are friendly and go above and beyond. I loved the wine available for purchase. Pietro was a great communicator and helpful with fabulous suggestions and support. I would come back in a heartbeat.
Guest favorite
Home in Castellina in Chianti
4.98 out of 5 average rating, 99 reviews

Explore Chianti from a Charming Stone House

ShelbyRating, 5 stars1 week ago
Best part of our Italy trip! We loved our stay at Casa Marinella, and Monica has thought of every detail to make for a wonderful and peaceful vacation! Relax by the pool and enjoy breathtaking views. Be sure to stop by Gelateria di Castellina for a scoop of cremino gelato and try the fiorentina steak at Osteria La Sosta di Pio VII.
Top guest favorite
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!
Top guest favorite
Home in Volterra
4.93 out of 5 average rating, 181 reviews

Collina Power

AlexandraRating, 5 starstoday
Beautiful and rustic farmhouse placed in ancient olive grove. We had six adults and were extremely comfortable for our two week stay. Some days we never got out of the clean and refreshing pool. Family dinners were prepared in the perfectly functional kitchen served in the courtyard dining table Nicola was always availableto answer whatever ever came up. Loved the house and our Tuscan vacation

Weekly house rentals

Top guest favorite
Home in Sticciano Scalo
4.95 out of 5 average rating, 39 reviews

Villa in Maremma

VickyRating, 5 stars8 months ago
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!
Top guest favorite
Home in Montemassi
4.96 out of 5 average rating, 50 reviews

Capezzuolo 33

BenRating, 5 stars2 weeks ago
This apartment was so beautiful and the views were even better. We had an amazing stay here as our base for exploring Tuscany - visiting the Val d’Orcia and the thermal baths were a highlight! Lucia and Marco met us on arrival and were extremely friendly and gave us plenty of advice and places to visit. There was an issue with the boiler but Lucia was straight on it and it was fixed by the time we were home for the day. Thank you so much!
Top guest favorite
Home in San Gimignano
4.98 out of 5 average rating, 41 reviews

Tuscany:Stone house, private pool and garden

MarceloRating, 5 stars1 week ago
This house is the perfect place for two families traveling together. It’s incredibly cozy, thoughtfully designed, and fully equipped with amenities that let you truly enjoy the beauty of the Tuscan countryside. From the moment we arrived, we felt at home. The hosts went above and beyond — welcoming us with fresh fruit, traditional sweets, bottled water, coffee, milk, and a selection of Tuscan wines, which we truly appreciated. They also provided high-quality Italian hygiene products, which added a thoughtful and luxurious touch to our stay. One of the highlights for us was the host’s responsiveness. Communication was always fast, helpful, and friendly — a detail that made a big difference. We didn’t get a chance to use the private pool due to our tight schedule, but the property still gave us a real sense of independence, comfort, and safety. I 100% recommend this property. It’s a peaceful, beautiful place — perfect for relaxing, connecting with nature, and creating memories
Top guest favorite
Home in Montalcino
5 out of 5 average rating, 8 reviews

New Palazzo in City Center: 4 King Bedrms 6 Bath

RiteshRating, 5 stars1 month ago
Thank you Brian for sharing your beautiful home with us for a couple of days. Your home is by far the best maintained and most well equipped and pristine places that we have stayed so far. We had the most amazing time in the house as well as walking around the city in the evenings. The location is perfect for everything from shopping to restaurants and wine tastings. Thank you Valentina for taking care of our needs during the stay, we would definitely return to stay at your house the next time when we visit. Thank you so much🙏
Top guest favorite
Home in Montalcino
4.94 out of 5 average rating, 33 reviews

Domus Antiqua

KellyRating, 5 stars2 months ago
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.
Superhost
Home in Lucignano
4.83 out of 5 average rating, 41 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.
Top guest favorite
Home in Roccastrada
5 out of 5 average rating, 81 reviews

Delightful loft surrounded by greenery with garden

ChiaraRating, 5 stars6 months ago
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.
Top guest favorite
Home in Sasso D'ombrone
5 out of 5 average rating, 30 reviews

Tosco Suite "Solis"

DinaRating, 5 stars1 week ago
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.

Private house rentals

Superhost
Home in Roccatederighi
4.83 out of 5 average rating, 6 reviews

Casadiluppe Typical dwelling in the Maremma hills.

IreneRating, 5 stars14 months ago
Mariagabriella's home has a great view, we found it easily, clean and tidy. It has everything you need and more. Mariagabriella is also very available for advice on the area.
Guest favorite
Home in Rosennano
4.93 out of 5 average rating, 80 reviews

LA RONDINAIA. AMAZING VIEW ABOVE THE CHIANTI

KaterinaRating, 5 stars1 week ago
Sebastiano’ place a real heaven in the heart of Chianti mountains in Tuscany. Amazing project, wonderful nature and history everywhere around. Place is so peaceful and unique. Just a dream which came true!
Superhost
Home in Gambassi Terme
4.85 out of 5 average rating, 27 reviews

Finest country house. 3 bed rooms and shared pool

HelenRating, 5 stars10 months ago
Enjoyable stay. Close to many beautiful towns.
Top guest favorite
Home in Monticchiello
5 out of 5 average rating, 41 reviews

Lovely home to dream

CadeRating, 5 stars1 week ago
This place is definitely a piece of Tuscany Italy. it will always hold a special place in my wife's and my heart with how beautiful and amazing the house was and the town it is located in. it seemed very well located, close to hot springs, multiple other cities, beautiful country side with horse back riding, world class winery's, ect. She is a great host and I would highly recommend this Airbnb to anybody looking for a one of a kind experience in Italy.
Top guest favorite
Home in Volterra
4.98 out of 5 average rating, 56 reviews

CountryHouse immersed in woodland

AmirRating, 5 stars2 months ago
One of the best Airbnbs we stayed in with absolutely the best host we have ever met! Antonio was amazing. Before our arrival, he provided clear instructions and suggested to help for a smooth check in. He always made sure that we have what we need for a perfect stay, and even spoiled us with a few complementary wine and chocolate. Now, the place is amazing. From the balcony you get the best views in the region, surrounded by trees and immersed by the sound of birds around you. Truly pleasant, relaxing and restoring vacation. The house is fully equipped with EVERYTHING you need, very well maintained, and super clean. We didn't want to leave, and can't wait to get back again!
Guest favorite
Home in Contignano
4.95 out of 5 average rating, 20 reviews

Noi 2 Vacanze in Fortino d 'Amore

ShervinRating, 5 stars1 day ago
We had a great stay at Antonio’s Place. Tbh. the pictures of the interior look better than in real life, but the balcony with the view and the location itself is simply one of a kind that you instantly forget everything else. If you want to experience the beauty of Tuscany, this is the right apartment.
Guest favorite
Home in Montebenichi
4.9 out of 5 average rating, 70 reviews

Ancient stone house in Chianti

ThaoRating, 5 stars1 month ago
We rented the whole property to include the additional third room and we had a great time. Located in a remote and very quiet setting, the property provides an authentic Tuscan experience. It has a magnificent garden with a great view and a great pool. We saw wild boars and horses afar from the terrace every day. The outdoor dining area is spacious and very relaxing. Our hosts, Emilio and Simona, are very nice, responsive and accommodating during our entire stay. Thank you Emilio and Simona for your warm hospitality.
Guest favorite
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 97 reviews

Casa Luigi Suite with exclusive pool

DerekRating, 5 stars4 days ago
I looked at dozens of other ABBs before choosing Giovanna's place and I know I made the best choice after staying. The setting is absolutely beautiful and peaceful. Lounging at the pool was so nice. We had the pool all to ourselves which is hard to find with other ABBs. The home is a nice large space and very clean. The views out the window are great. Giovanna was so nice and welcoming just a wonderful person. We enjoyed having a drink with her and Luigi. I highly recommend her place.

Destinations to explore

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