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 swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

1. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is AU$8,950
includes taxes & fees
26 Oct - 27 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
A rural property with stone buildings, a garden, and a view of rolling hills.

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is AU$715
includes taxes & fees
1 Oct - 2 Oct
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
A villa with a swimming pool, surrounded by lush greenery and vineyards.

3. 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$9,730
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
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$3,009
includes taxes & fees
23 Oct - 24 Oct
"A Casa di Franca Villa con piscina"
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

5. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is AU$215
includes taxes & fees
1 Oct - 2 Oct
Rooster House, cooking classes and opera
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
The price is AU$1,685
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.

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 AU$4,379
includes taxes & fees
5 Oct - 6 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A two-story building with a garden, a gazebo, and a statue.

8. 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 AU$6,988
includes taxes & fees
2 Oct - 3 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A two-story building with a red roof, multiple windows, and a gravel driveway.

9. 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 AU$2,696
includes taxes & fees
2 Oct - 3 Oct
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

10. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is AU$310
includes taxes & fees
7 Oct - 8 Oct
Villa Le Polle di Meletro
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

11. 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 AU$595
includes taxes & fees
12 Oct - 13 Oct
Luxury Villa in the Florentine hills
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

12. 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$268
includes taxes & fees
3 Oct - 4 Oct
Villa Montecastello
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

13. 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$3,158
includes taxes & fees
3 Oct - 4 Oct
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
A covered balcony with a brick railing, a bench, and a view of lush greenery.

14. 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$945
includes taxes & fees
2 Oct - 3 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AU$8,605
includes taxes & fees
8 Oct - 9 Oct
Villa "Arnilù" with Private Pool & Wi-Fi
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

16. 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$3,158
includes taxes & fees
3 Oct - 4 Oct
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.

17. Villa Belvedere with Private Pool and Volterra Views

Villa Belvedere with Private Pool and Volterra Views
Gambassi Terme
The price is AU$3,084
includes taxes & fees
1 Oct - 2 Oct
Villa Belvedere with Private Pool and Volterra Views
A multi-story residential building with a stone wall in front, a balcony on the second floor, and a lit entrance.

18. Villa Cattleya

Villa Cattleya
Casciana Terme
10.0 out of 10, Exceptional, (1 review)
"Tout était impeccable. "
France
Stéphane S.
Villa Cattleya
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

19. 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 AU$600
includes taxes & fees
1 Oct - 2 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
A rural property with stone buildings, a garden, and a view of rolling hills.

20. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is AU$777
includes taxes & fees
2 Oct - 3 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

Italiana Hotels Florence

Italiana Hotels Florence

8/10 Good
"Greta place and friendly staff. Pool closed early in the month due to rain that was disappointing"
Jodie 2-night trip
Posted 3 hours ago
Italiana Hotels Florence

Find out more about Castelfiorentino

Castelfiorentino Villas information

Number of reviews
215
Accommodation
1357 Villas
Lowest Price
AU$215
Highest Price
AU$9,730