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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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 NZ$257
includes taxes & fees
30 Oct - 31 Oct
Rooster House, Cooking Classes, and Opera
A modern poolside area with a clear view of the landscape.

2. Aureva Tuscany, modern villa with private pool

Aureva Tuscany, modern villa with private pool
Montelupo F.no
The price is NZ$1,155
includes taxes & fees
1 Nov - 2 Nov
Aureva Tuscany, modern villa with private pool
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

3. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is NZ$372
includes taxes & fees
2 Nov - 3 Nov
Villa Le Polle di Meletro
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

4. 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 NZ$327
includes taxes & fees
30 Oct - 31 Oct
Villa Montecastello
A person in a swimming pool with a view of a vineyard and hills.

5. "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 NZ$3,029
includes taxes & fees
2 Nov - 3 Nov
"A Casa di Franca Villa con piscina"
A table set for tea with a view of a garden and hills.

6. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
Tuscan Sky Villa in San Miniato with Private Pool
A building with a large entrance, potted plants, and a statue in the foreground.

7. 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 NZ$3,177
includes taxes & fees
1 Nov - 2 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
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

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 NZ$3,544
includes taxes & fees
2 Nov - 3 Nov
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

9. 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 NZ$2,802
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A covered balcony with a brick railing, a bench, and a view of lush greenery.

10. 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 NZ$2,277
includes taxes & fees
2 Nov - 3 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A villa with a swimming pool, surrounded by lush greenery and vineyards.

11. 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 NZ$10,586
includes taxes & fees
2 Nov - 3 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A courtyard with a building, potted plants, and a grassy area.

12. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Toscana
The price is NZ$4,294
includes taxes & fees
2 Nov - 3 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

13. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is NZ$633
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A rural property with stone buildings, a garden, and a view of rolling hills.

14. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is NZ$4,893
includes taxes & fees
30 Oct - 31 Oct
Villetta Brunelleschi: Privacy and Comfort on Two Levels
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

15. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (4 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
A stone building with a large arched entrance, potted plants, and outdoor seating.

16. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 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 NZ$1,826
includes taxes & fees
1 Nov - 2 Nov
Exclusive Estate | Personal Concierge & Heated Pool
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

17. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A terrace with stone walls, a view of the landscape, and outdoor furniture including a chair and a table.

18. 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 NZ$1,171
includes taxes & fees
26 Nov - 27 Nov
Antico Borghetto di Tigliano: Cozy and ideal for families with children
A swimming pool with a stone deck, a covered patio with outdoor furniture, and a view of mountains in the background.

19. Casa Il Cappero – Villa with Private Pool in the Tuscan Hills

Casa Il Cappero – Villa with Private Pool in the Tuscan Hills
San Rocco
The price is NZ$2,274
includes taxes & fees
2 Nov - 3 Nov
Casa Il Cappero – Villa with Private Pool in the Tuscan Hills
A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

20. 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 NZ$18,492
includes taxes & fees
27 Nov - 28 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
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

Villa Neroli - Place of Charme

Villa Neroli - Place of Charme

10/10 Excellent
"Great stay"
Bridgette 1-night trip
Posted 12 hours ago
Villa Neroli - Place of Charme

Find out more about Castelfiorentino

Castelfiorentino Villas information

Number of reviews
332
Accommodation
1360 Villas
Lowest Price
NZ$257
Highest Price
NZ$18,492