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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Castelfiorentino villas

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

1. 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 £142
includes taxes & fees
3 Oct - 4 Oct
Villa Montecastello
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 £115
includes taxes & fees
5 Oct - 6 Oct
Rooster House, cooking classes and opera
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 £180
includes taxes & fees
7 Oct - 8 Oct
Villa Le Polle di Meletro
A rural property with stone buildings, a garden, and a view of rolling hills.

4. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is £377
includes taxes & fees
3 Oct - 4 Oct
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
A two-story building with a garden, a gazebo, and a statue.

5. 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
The price is £3,675
includes taxes & fees
8 Oct - 9 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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 £497
includes taxes & fees
14 Oct - 15 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A person in a swimming pool with a view of a vineyard and hills.

7. "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 £1,582
includes taxes & fees
30 Oct - 31 Oct
"A Casa di Franca Villa con piscina"
A two-story building with a red roof, multiple windows, and a gravel driveway.

8. Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Empoli
10.0 out of 10, Exceptional, (1 review)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
United States
Vicki C.
The price is £1,421
includes taxes & fees
4 Oct - 5 Oct
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
A stone building with a large glass door, a wooden deck, and a stone wall.

9. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is £4,525
includes taxes & fees
5 Oct - 6 Oct
Villa "Arnilù" with Private Pool & Wi-Fi
A table set for tea with a view of a garden and hills.

10. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
The price is £886
includes taxes & fees
4 Oct - 5 Oct
Tuscan Sky Villa in San Miniato with Private Pool
A building with a large entrance, potted plants, and a statue in the foreground.

11. 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 £1,536
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 vineyards.

12. 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 £5,116
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

13. 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 £1,668
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A villa with a swimming pool, surrounded by lush greenery and hills.

14. Villa Belvedere with Private Pool and Volterra Views

Villa Belvedere with Private Pool and Volterra Views
Gambassi Terme
The price is £1,622
includes taxes & fees
8 Oct - 9 Oct
Villa Belvedere with Private Pool and Volterra Views
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

15. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 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 £288
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

16. 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 £334
includes taxes & fees
16 Oct - 17 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Terrace/patio

17. Tenuta le Viste - beautiful Villa overlooking Florence

Tenuta le Viste - beautiful Villa overlooking Florence
scandicci
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful house"
France
STEPHANE B.
Tenuta le Viste - beautiful Villa overlooking Florence
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

18. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is £11,101
includes taxes & fees
7 Oct - 8 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A rural property with stone buildings, a garden, and a view of rolling hills.

19. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is £410
includes taxes & fees
3 Oct - 4 Oct
Villetta Brunelleschi: Privacy and Comfort on Two Levels
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

Villa Neroli

10/10 Excellent
"The property was magnificent - much nicer than what was depicted in the web photos. The staff was exceptional ... whether it was the administrative staff, the servers, or the cleaning staff, all realized that they were there to service their guests and they provided quality services consistently during our stay. The breakfast was exceptional. A very pleased guest!"
john 7-night trip
Posted 8 hours ago
Villa Neroli

Find out more about Castelfiorentino

Castelfiorentino Villas information

Number of reviews
206
Accommodation
1679 Villas
Lowest Price
£115
Highest Price
£11,101