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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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

Aureva Tuscany, modern villa with private pool
Montelupo F.no
Aureva Tuscany, modern villa with private pool
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is €135
includes taxes & fees
15 Oct - 16 Oct
Rooster House, cooking classes and opera
A clear swimming pool with lounge chairs and a green umbrella.

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

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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)
The price is €185
includes taxes & fees
16 Oct - 17 Oct
Villa Montecastello
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

5. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is €194
includes taxes & fees
17 Oct - 18 Oct
Villa Le Polle di Meletro
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

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 €583
includes taxes & fees
15 Oct - 16 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
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.
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

8. 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 €1,930
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A table set for tea with a view of a garden and hills.

9. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
The price is €1,040
includes taxes & fees
1 Nov - 2 Nov
Tuscan Sky Villa in San Miniato with Private Pool
A person in a swimming pool with a view of a vineyard and hills.

10. "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 €1,857
includes taxes & fees
6 Nov - 7 Nov
"A Casa di Franca Villa con piscina"
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
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (151 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
Luxury Villa in the Florentine hills
Outdoor dining

13. Tenuta le Viste—a magnificent villa overlooking Florence

Tenuta le Viste—a magnificent villa overlooking Florence
scandicci
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful house"
France
STEPHANE B.
Tenuta le Viste—a magnificent villa overlooking Florence
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 €2,498
includes taxes & fees
15 Oct - 16 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. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 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.
The price is €391
includes taxes & fees
15 Oct - 16 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
A courtyard with a building, potted plants, and a grassy area.

16. 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
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. 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 €1,114
includes taxes & fees
19 Oct - 20 Oct
Exclusive Estate | Personal Concierge & Heated Pool
Property grounds

18. Incredible villa in the Tuscan countryside

Incredible villa in the Tuscan countryside
Vinci
10.0 out of 10, Exceptional, (1 review)
"Overall, great experience, clean house, beautiful views!"
United States
Marianna K.
Incredible villa in the Tuscan countryside
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
Casa Il Cappero – Villa with Private Pool in the Tuscan Hills
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 Santa Maria Novella

Hotel Santa Maria Novella

10/10 Excellent
"Definitely will book this place on next trip to Florence. Location was perfect and place is top notch not to mention the incredible breakfast. 5 great restaurants within in 3 blocks and the church in the square is a must see."
Renee 2-night trip
Posted 8 hours ago
Hotel Santa Maria Novella

Find out more about Castelfiorentino

Castelfiorentino Villas information

Number of reviews
322
Accommodation
1679 Villas
Lowest Price
€135
Highest Price
€2,498

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