Castelfiorentino Villas

Rolling hills, vineyards, and scattered buildings in a hilly landscape.

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Our top choices for Castelfiorentino villas

A modern poolside area with a clear view of the landscape.

1. Aureva Tuscany, modern villa with private pool

Montelupo F.no

HK$5,278 total

includes taxes & fees

1 Nov - 2 Nov

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

HK$1,151 total

includes taxes & fees

14 Oct - 15 Oct

A curved stone pathway leading to a pool area with a view of the surrounding landscape.

3. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Gambassi Terme

HK$37,904 total

includes taxes & fees

15 Oct - 16 Oct

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

4. Villa Montecastello

Monteriggioni

Alvaro

HK$1,628 total

includes taxes & fees

16 Oct - 17 Oct

A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

5. Villa Le Polle di Meletro

Rivalto

HK$1,665 total

includes taxes & fees

16 Oct - 17 Oct

A covered balcony with a brick railing, a bench, and a view of lush greenery.

6. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Certaldo - Firenze

Kelly C.

HK$5,124 total

includes taxes & fees

13 Oct - 14 Oct

A building with a large entrance, potted plants, and a statue in the foreground.

7. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

HK$14,257 total

includes taxes & fees

1 Nov - 2 Nov

A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

8. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Montespertoli

"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"

Elise D.

HK$16,437 total

includes taxes & fees

1 Nov - 2 Nov

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Top Castelfiorentino Hotel Reviews

Plus Florence - Hostel

10/10 Excellent

"Facilities are very nice. Easy access to everything. Staff is friendly and helpful. Would stay here again anytime!"

Hotel Horto Convento

10/10 Excellent

"This hotel was exceptional! The grounds were beautiful. The staff was extremely helpful. The location was perfect. The only downside was they don't have smart TVs and limited stations in English. We have to sleep to TV, but they are getting them soon. Otherwise, I cannot say enough wonderful things about our stay. We will be back!"

Find out more about Castelfiorentino