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Compare 236 Villas in Sassofortino with updated reviews, rates, and availability.

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Terrace/patio
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
10.0 out of 10, Exceptional, (93)
"We had the most amazing stay at this beautiful villa. Everything about it was picturesque and relaxing. This villa has all of the modern amenities but still exudes Tuscan charm. Pre- visit communication was smooth and very prompt. The highlight of the stay was the dinner cooked for us the first night by Chef Vanna and Francesca. I am not exaggerating when I say it was by far the best meal we had during our trip to Tuscany and we ate at many very nice restaurants. If you are booking a stay I...
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
Terrace/patio
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
10.0 out of 10, Exceptional, (71)
"We so enjoyed our nine nights at Leo’s beautiful place in Belforte. This is a tiny Medieval town at the top of the mountain. So quiet except for the church bells, and occasional kids running through the town. A nice retreat from the business of other Tuscany tourist attractions. The home is very spacious with four bedrooms and large outdoor gathering areas . Fruit trees and grape vines in the yard add to the ambiance . The kitchen was well equipped, with everything one would need and the...
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Living area
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
9.6 out of 10, Exceptional, (37)
"Our family had a fantastic time in this rural villa. The space was very clean and well-kept as were the grounds (almost too much as they were there mowing grass several times during our stay and for most of the day). The surroundings were very peaceful and quiet and the countryside views were breathtaking with many outdoor areas on the property to enjoy - perfect for meals al fresco! Property is wonderfully located and ideal for day trips in Tuscany/Umbria from this home base but made sure we...
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Villa with private swimming pool in quiet area, private garden, panoramic views
Pool
Villa with private swimming pool in quiet area, private garden, panoramic views
10.0 out of 10, Exceptional, (8)
"La maison est très calme, très propre et bien équipée, accessible en partie par un chemin de terre depuis le joli village de Radicondoli, . La vue sur les collines avoisinantes est très agréable, en particulier de la piscine (hors-sol). Il faut compter environ 45 minutes de jolies routes pour se rendre à Sienne, Volterra ou San Giminiano. Beaucoup d'animaux sauvages dans la nature, si vous êtes chanceux comme nous... Sarka est une hôtesse sympathique et attentionnée. Avec son mari, elle produit...
Villa with private swimming pool in quiet area, private garden, panoramic views
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
The property has a private road and gate
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
9.8 out of 10, Exceptional, (9)
"The villa is beautiful, spacious, clean and comfortable. The location is excellent. There are horses and ponies on the grounds. The best part is the hostess and the host. They are so accomadating and kind. The pasta we dinner and pizza party were great! "
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
panoramica casa con piscina privata
Pool
panoramica casa con piscina privata
7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
panoramica casa con piscina privata
A private luxury retreat in Montalcino
The veranda at sunset
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (55)
"Lovely villa, great host. We really enjoyed our stay. "
A private luxury retreat in Montalcino
villa con vista panoramica
Pool
villa con vista panoramica
9.0 out of 10, Wonderful, (2)
"Die Wohnung liegt ruhig im schönen Dorf Chiusdino, das Meer ist ca. 1 Stunde entfernt, aber der Pool eignet sich gut zum Baden. Es ist genug Platz für 4 Personen. Der Vermiter Paolo ist sehr freundlich und hilfsbereit, die Kommunikation war super. Uns hat es sehr gut gefallen und wir kommen gerne wieder!"
villa con vista panoramica
Villa Costa, Stunning Villa in the heart of Tuscany.
Pool
Villa Costa, Stunning Villa in the heart of Tuscany.
10.0 out of 10, Exceptional, (32)
"I stayed at this property for 1 week with my parents, my sisters and their husbands and 3 children (aged 1-6) and all I can say is what a wonderful villa. The layout was ideal for us. 3 bedrooms were located upstairs accessed by the external stairs, 2 had en-suites and the other had a bathroom next door) and there was also a seating area up there. One bedroom was based downstairs off the main living area with a bathroom next door. And the other bedroom was in the annexe which was accessed...
Villa Costa, Stunning Villa in the heart of Tuscany.
Delightful villa in the heart of Tuscany
villa LeBolli Siena villa for holiday
Delightful villa in the heart of Tuscany
10.0 out of 10, Exceptional, (54)
"Villa Le Bolli was an amazing venue. The staff made us feel welcome and feel as if the house was our own from the start. Sometimes, it is small touches that can make a big difference. With the help of the host, we had a pizza welcoming catered dinner. The host had a wedding before our stay and used the left over flower arrangements to add decorations for us. The sunsets were amazing and the kitchen had everything that was needed. The hosts were very generous with other things such as making sure...
Delightful villa in the heart of Tuscany
Villa di Piera
Living area
Villa di Piera
8.6 out of 10, Excellent, (4)
"Die Kommunikation mit dem Vermieter war gut, obwohl wir ihn erst zur Abfahrt persönlich getroffen haben. Bei Ankunft stellten wir fest, dass ein Zimmer belegt war und nicht wie bei FE-Wo de beschrieben, 4 Zimmer zur Verfügung standen. Das war aber das einzige, was wir zu bemängeln haben. Das Haus ist gemütlich, mit modernen Duschen, Klimaanlage und Ventilator eingerichtet, wofür wir bei 37 Grad sehr dankbar waren. Im Außenbereich kann man sich gut aufhalten. Parken ist auch möglich. Da wir...
Villa di Piera
Villa Dipendenza, Historic Holding with wonderful swimming pool
Exterior
Villa Dipendenza, Historic Holding with wonderful swimming pool
10.0 out of 10, Exceptional, (35)
"We spent a week at this charming property and had an absolutely magical time with friends. The house was cozy and comfortable, with a beautiful balcony perfect for enjoying evening meals. The shared pool offered breathtaking views, and the other guests were incredibly friendly, adding to the warm atmosphere. Our host, Eloise, was exceptional—her hospitality and attention to detail made our stay even more special. She provided wonderful restaurant recommendations that we thoroughly enjoyed. We...
Villa Dipendenza, Historic Holding with wonderful swimming pool
Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma
Outdoor spa tub
Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma
9.8 out of 10, Exceptional, (18)
"It was a perfect stay! Very helpful hosts with great local suggestions."
Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma
Luxurious 19th-Century Villa with Saline Pool in Maremma, a few Km from the Sea
Pool
Luxurious 19th-Century Villa with Saline Pool in Maremma, a few Km from the Sea
10.0 out of 10, Exceptional, (75)
"The villa was incredible, and allowed our entire family to stay together. The grounds and pool were breath-taking and complete with a hammock, barbecue, outdoor games and toys, and lots of sitting areas. Large tables indoors and out provided space for meals and games. The location was perfect for exploring nearby towns, beaches, and trails by car or bicycle. I just can’t say enough about the facilities or about the prompt and cheerful responses from the owner/his representative when we called on...
Luxurious 19th-Century Villa with Saline Pool in Maremma, a few Km from the Sea
Stunning Villa: 24 guests, private SwimmingPool
Pool
Stunning Villa: 24 guests, private SwimmingPool
10.0 out of 10, Exceptional, (27)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool
Historic Holding with wonderful swimming pool near Siena, Tuscany, Italy
La Palazzina main villa
Historic Holding with wonderful swimming pool near Siena, Tuscany, Italy
10.0 out of 10, Exceptional, (8)
"Tutto come ce lo aspettavamo, il chè non sempre avviene ma in questo caso SI."
Historic Holding with wonderful swimming pool near Siena, Tuscany, Italy
Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday
Aereal view of the villa
Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday
10.0 out of 10, Exceptional, (33)
"We all had a wonderful holiday. The villa was lovely and so well equipped. The garden, hot tub and especially the pool were amazing!! Gina and Franco were so kind to bring us wonderful treats during the stay and left a very generous welcome basket. Absolutely fantastic place for a holiday. We hope to return one day!"
Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday
Architectural Digest Masterpiece 18th Century Tuscan Villa
Pool
Architectural Digest Masterpiece 18th Century Tuscan Villa
9.0 out of 10, Wonderful, (13)
"This property is truly isolated, about two hours drive from Florence airport. A robust vehicle is required as the roads of Tuscany are a little rundown and the access to Le Tanelle is an unmade, steep drive. The view and isolation is worth the effort. There have been changes to the property since the marketing photographs on the site. Some improvements like safety cables around the pool area making it safer for children other elements of the building have moved on as the restoration is a work in...
Architectural Digest Masterpiece 18th Century Tuscan Villa
Antico Convento I Cappuccini - Villa & Wedding Venue
Exterior
Antico Convento I Cappuccini - Villa & Wedding Venue
10.0 out of 10, Exceptional, (2)
"Convent I Cappuccini was amazing. We (18 family members) spent a week here in early July 2022. The rooms are so beautiful and simply appointed. There were absolutely no complaints from the group. We loved the pool, the forest walks, early morning runs to Montalcino, lovely dinners on the patio, and day trips to close by hill towns. This house is a perfect venue for a wedding, family reunions or conferences. Riccardo kept the pool sparkling and was a great host. Thank you."
Antico Convento I Cappuccini - Villa & Wedding Venue
House / Villa - Bagno di GavorranoHouse with garden
Pool
House / Villa - Bagno di GavorranoHouse with garden
10.0 out of 10, Exceptional, (3)
"We stayed 2 weeks and it was wonderful! The house is very nice and spacious as is the garden. And the swmingpool is great of course, especially during the warm days. Location is great as well: close to beaches, lovely towns and restaurants."
House / Villa - Bagno di GavorranoHouse with garden
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Sassofortino

Bosco della Spina
Exterior
Bosco della Spina
9.4 out of 10, Exceptional, (140)
"We were met by the property owner who was pleasant and informative. The room was exactly as depicted in the photos and property was in excellent condition. We would recommend to anyone staying the area at any time of year/ "
Bosco della Spina
agriturismo la roggiola
Property grounds
agriturismo la roggiola
9.6 out of 10, Exceptional, (94)
"Cute rustic cottage with a beautiful restful view of farm land and forrested hills and a covered outdoor eating area."
agriturismo la roggiola
panoramica casa con piscina privata
Pool
panoramica casa con piscina privata
7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
panoramica casa con piscina privata
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.