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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Pontassieve

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Outdoor pool

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle

9.6 out of 10, Exceptional, (19)
"More than we imagined for our Tuscany vacation. Spacious, well appointed and clean. Marzio was an excellent host with knowledge of the area and its history. He gave wonderful suggestions for wines, restaurants and touring excursions. We highly recommend this historical villa for a Tuscany vacation!"
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Happy holidays in Chianti, among olives and vineyards, From Florence
Pool

Happy holidays in Chianti, among olives and vineyards, From Florence

9.8 out of 10, Exceptional, (17)
"A lovely little cottage in beautiful surroundings and perfectly situated to discover Tuscany. Elisabeth is lovely and very friendly and helpful and Oliver is brilliant"
Happy holidays in Chianti, among olives and vineyards, From Florence
Typical Tuscan Countryside Cottage near Florence
Property grounds

Typical Tuscan Countryside Cottage near Florence

10.0 out of 10, Exceptional, (28)
"We really enjoyed our stay and we can highly recommend this lovely cottage."
Typical Tuscan Countryside Cottage near Florence
Charming Farmhouse with Private Pool among Vineyards
Outdoor pool, a heated pool

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (50)
"We stayed here with our family as a large group of 8 adults and 1 infant. The layout of the house worked great, each couple had their own room (even our daughter) and their own bathroom! Our daughter loved the pool and the property had everything we needed. The location was great, our group took day trips to explore Siena, Florence, and wine country. The winery on the property was also fantastic! A great place to say and I highly recommend it!"
Charming Farmhouse with Private Pool among Vineyards
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Outdoor pool

Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities

9.8 out of 10, Exceptional, (31)
"This is a great location to experience the beauty of Tuscany. People interested in history find this place even more interesting and mystical. Check out the history on their website. Owners did an incredible job restoring the beauty of this place. The entire family lives on site , so it so convenient to seek their advise. They are very helpful and knowledgeable and for us it felt like we were with family. I would definitely recommend this place to my friends and family members. We loved our 5...
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Pool

Exceptionally pretty cottage with pool, views, in walking distance from Panzano

10.0 out of 10, Exceptional, (43)
"Superb location / great scenery Lucrezia is a welcoming hostess "
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Stone cottage on heritage Chianti estate-pool-tennis
Pool

Stone cottage on heritage Chianti estate-pool-tennis

Stone cottage on heritage Chianti estate-pool-tennis
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
Outdoor dining

Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.

10.0 out of 10, Exceptional, (9)
"It was a great stay and Laura is a very friendly and helpful host who was also able to give excellent tips for trips. But also the cottage and pool were fantastically beautiful. We enjoyed it very much."
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
La Misura, cottage with garden and swimming pool on the hills of Chianti
Outdoor dining

La Misura, cottage with garden and swimming pool on the hills of Chianti

10.0 out of 10, Exceptional, (2)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
La Misura, cottage with garden and swimming pool on the hills of Chianti
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
Outdoor pool

Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two

9.8 out of 10, Exceptional, (10)
"Apart from the spacious,well equipped cottage and overall calm and relaxing environment with great pool and outdoor eating area, Marzio, Adela and Mauro were the perfect hosts providing us with very practical advice on what to see and do in the region. Cellole is also very well situated to explore the region, half way between Florence and Sienna it allowed us to visit these cities or explore the many medieval fortress villages close by. The cooking course we did was a real highlight. My daughter...
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
Typical country house with garden near Florence Siena Pisa San Gimignano
Outdoor dining

Typical country house with garden near Florence Siena Pisa San Gimignano

9.6 out of 10, Exceptional, (48)
"We enjoyed some days in this beautiful area"
Typical country house with garden near Florence Siena Pisa San Gimignano
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Property grounds

La Quercia, apartment with garden for 6/8 people in the heart of Chianti

10.0 out of 10, Exceptional, (2)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Belvilla by OYO Cottage in Tavarnelle With Garden
Cottage | Pool | Outdoor pool

Belvilla by OYO Cottage in Tavarnelle With Garden

Belvilla by OYO Cottage in Tavarnelle With Garden
Casa Antico Roseto - cottage with swimming pool
Dining

Casa Antico Roseto - cottage with swimming pool

8.0 out of 10, Very Good, (1)
"The villa is lovely. The property is amazing. Check-in and out were easy and the owners are very kind. The only complaint we really had with our stay was that it is probably not the best place to stay during the summer months when it is 95+ outside. The villa has no air conditioning and even the fans they provided us did not prepare us for the heat inside even late at night. When we opened the windows we had a lot of mosquitoes and other bugs enter the house so we were forced to close up most of...
Casa Antico Roseto - cottage with swimming pool
Paolina house, typical Tuscan structure with pool, surrounded by nature
Outdoor dining

Paolina house, typical Tuscan structure with pool, surrounded by nature

10.0 out of 10, Exceptional, (2)
"Just perfect !"
Paolina house, typical Tuscan structure with pool, surrounded by nature
The Arsoli hut .Swimming pool exclusive use.
Outdoor pool, an infinity pool

The Arsoli hut .Swimming pool exclusive use.

10.0 out of 10, Exceptional, (23)
"Silvia and her family were great. The property was clean, very well furnished and I would definitely go back. If you are thinking of staying in this area, then this one is a YES!"
The Arsoli hut .Swimming pool exclusive use.
La Chiantinelle - La Grange
Interior

La Chiantinelle - La Grange

La Chiantinelle - La Grange
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Outdoor dining

Cottage "Podere in Volpaia" with Garden & Wi-Fi

10.0 out of 10, Exceptional, (3)
"Pros: Jede Menge Platz. Tolle Atmosphäre, idyllisch gelegen. Die Gastgeberin war immer erreichbar und äußerst nett. Der Wein war lecker 😋"
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Belvilla by Oyo La Casa dei Cinque Olivi
House | Pool | Outdoor pool

Belvilla by Oyo La Casa dei Cinque Olivi

Belvilla by Oyo La Casa dei Cinque Olivi
Casa Belvedere cottage with swimming pool in the heart of Chianti
Pool

Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
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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