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

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Castelfiorentino villas

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

1. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is AU$191
includes taxes & fees
15 Nov - 16 Nov
Rooster House, Cooking Classes, and Opera
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

2. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
Villa Le Polle di Meletro
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

3. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is AU$2,240
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A person in a swimming pool with a view of a vineyard and hills.

4. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveller
The price is AU$2,479
includes taxes & fees
15 Nov - 16 Nov
"A Casa di Franca Villa con piscina"
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

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

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"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!"
United States
Elise D.
The price is AU$2,223
includes taxes & fees
9 Dec - 10 Dec
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
A building with a large entrance, potted plants, and a statue in the foreground.

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

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is AU$2,633
includes taxes & fees
15 Nov - 16 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and vineyards.

7. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is AU$8,772
includes taxes & fees
15 Nov - 16 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A covered balcony with a brick railing, a bench, and a view of lush greenery.

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

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is AU$1,887
includes taxes & fees
15 Nov - 16 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

9. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AU$22,985
includes taxes & fees
16 Nov - 17 Nov
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A stone building with a large arched entrance, potted plants, and outdoor seating.

10. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
impruneta
10.0 out of 10, Exceptional, (117 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is AU$1,958
includes taxes & fees
18 Nov - 19 Nov
Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

11. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AU$571
includes taxes & fees
27 Nov - 28 Nov
Villa Montecastello
A terrace with a table and chairs, potted plants, and a stone wall.

12. Antico Borghetto di Tigliano: Cozy and ideal for families with children

Antico Borghetto di Tigliano: Cozy and ideal for families with children
Vinci
The price is AU$864
includes taxes & fees
18 Nov - 19 Nov
Antico Borghetto di Tigliano: Cozy and ideal for families with children
A large, historic building with multiple arches and a prominent tower.

13. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is AU$15,323
includes taxes & fees
15 Nov - 16 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
A garden with roses and a view of distant hills.

14. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is AU$4,660
includes taxes & fees
16 Nov - 17 Nov
Golden Hour - Wedding in Florence
A large estate with a swimming pool, tennis court, and multiple guest rooms.

15. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is AU$19,154
includes taxes & fees
29 Nov - 30 Nov
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
A building with a green facade, a wooden ceiling, and a balcony with potted plants.

16. VILLA FRANCO

VILLA FRANCO
Castelfranco di Sotto
The price is AU$811
includes taxes & fees
15 Nov - 16 Nov
VILLA FRANCO
A rectangular swimming pool with a view of mountains and a clear sky.

17. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16
Firenze
The price is AU$3,448
includes taxes & fees
15 Nov - 16 Nov
VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16
A poolside area with lounge chairs and a pergola.

18. Bagno a Ripoli, Italy. Entire property: Villa

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is AU$1,195
includes taxes & fees
16 Nov - 17 Nov
Bagno a Ripoli, Italy. Entire property: Villa
An outdoor seating area with a glass-top table and cushioned chairs, overlooking a lush garden and distant hills.

19. Villa Dei Pavoni - Luxury Villa in the Hills of Florence

Villa Dei Pavoni - Luxury Villa in the Hills of Florence
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is AU$2,686
includes taxes & fees
16 Nov - 17 Nov
Villa Dei Pavoni - Luxury Villa in the Hills of Florence
A white building with a tiled roof, surrounded by greenery and a winding road.

20. Florence Apartments - Villa Fonte Morgana with Pool

Florence Apartments - Villa Fonte Morgana with Pool
Impruneta
10.0 out of 10, Exceptional, (1 review)
"What a beautiful villa! We thoroughly enjoyed our stay in Tuscan countryside. All rooms were comfortable and large. We were surprised by the lack of body soap and shampoo."
United States
Christine B.
Florence Apartments - Villa Fonte Morgana with Pool
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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Top Castelfiorentino Hotel Reviews

Hotel Paris

Hotel Paris

10/10 Excellent
"Great central location. Old and characterful building with very high ceilingsand attractive furnishings. Good breakfast room with a decent choice of buffet breakfast. The breakfast room is then available all day with the left over morning pastries with endless hot drinks available all day. Extremely helpful and courteous staff. Room made up every day. The Borgello Museum is a must see not mentioned too much but ery interesting 12 euros each."
Loraine 8-night trip
Posted 5 hours ago
Hotel Paris

Find out more about Castelfiorentino

Castelfiorentino Villas information

Number of reviews
181
Accommodation
1357 Villas
Lowest Price
AU$191
Highest Price
AU$22,985