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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Castelfiorentino villas

Exterior detail

1. The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is ￥16,167
￥19,796 total
includes taxes & fees
Sep 18 - Sep 19
The three owls of san gimignano
Exterior

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is ￥62,273
￥80,055 total
includes taxes & fees
Oct 2 - Oct 3
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Outdoor dining

3. Tuscan Sky Villa in San Miniato with Exclusive Private Pool

Tuscan Sky Villa in San Miniato with Exclusive Private Pool
San Miniato
The price is ￥61,930
￥115,286 total
includes taxes & fees
Sep 14 - Sep 15
Tuscan Sky Villa in San Miniato with Exclusive Private Pool
Pool

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 traveler
The price is ￥262,314
￥341,397 total
includes taxes & fees
Sep 10 - Sep 11
"A Casa di Franca Villa con piscina"
Property grounds

5. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is ￥19,959
￥23,769 total
includes taxes & fees
Sep 6 - Sep 7
Rooster House, cooking classes and opera
Exterior

6. 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 ￥667,649
￥668,201 total
includes taxes & fees
Oct 1 - Oct 2
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Exterior

7. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is ￥412,541
￥471,148 total
includes taxes & fees
Sep 17 - Sep 18
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Exterior

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 ￥285,451
￥330,434 total
includes taxes & fees
Oct 3 - Oct 4
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Villa, Air conditioning, Courtyard View | Exterior

9. 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 ￥26,873
￥30,112 total
includes taxes & fees
Sep 6 - Sep 7
Villa Montecastello
Exterior

10. 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 ￥397,410
￥397,778 total
includes taxes & fees
Sep 8 - Sep 9
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior

11. Villa Cattleya

Villa Cattleya
Casciana Terme
10.0 out of 10, Exceptional, (1 review)
"Tout était impeccable. "
France
Stéphane S.
The price is ￥16,330
￥22,862 total
includes taxes & fees
Sep 18 - Sep 19
Villa Cattleya
Exterior

12. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is ￥69,241
￥87,023 total
includes taxes & fees
Oct 2 - Oct 3
Villetta Brunelleschi: Privacy and Comfort on Two Levels
Terrace/patio

13. 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 ￥92,891
￥115,330 total
includes taxes & fees
Sep 5 - Sep 6
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Pool

14. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is ￥29,458
￥40,209 total
includes taxes & fees
Oct 2 - Oct 3
Villa Le Polle di Meletro
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is ￥908,713
￥976,946 total
includes taxes & fees
Sep 11 - Sep 12
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

16. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"We loved this villa! David, our host, was very prompt in responding and providing additional information. The property was beautiful. We will definitely stay here again."
United States
John G.
The price is ￥45,362
￥70,220 total
includes taxes & fees
Sep 20 - Sep 21
Luxury Villa in the Florentine hills
Outdoor dining

17. 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 ￥51,205
￥68,987 total
includes taxes & fees
Sep 13 - Sep 14
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

18. Tuscan Villa with Private Pool, Terrace and Wi-Fi

Tuscan Villa with Private Pool, Terrace and Wi-Fi
Capraia e Limite
The price is ￥609,666
￥688,415 total
includes taxes & fees
Sep 28 - Sep 29
Tuscan Villa with Private Pool, Terrace and Wi-Fi
Property grounds

19. Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning

Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning
Legoli
The price is ￥232,419
￥287,615 total
includes taxes & fees
Sep 6 - Sep 7
Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning
Exterior

20. Villa Linchiano with Historic Tower and Private Pool

Villa Linchiano with Historic Tower and Private Pool
Gambassi Terme
The price is ￥478,364
￥478,916 total
includes taxes & fees
Sep 23 - Sep 24
Villa Linchiano with Historic Tower and Private 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 staff, great room, great Location!"
Steven 4-night trip
Posted 7 hours ago
Hotel Paris

Find out more about Castelfiorentino

Castelfiorentino Villas information

Number of reviews
160
Accommodation
1756 Villas
Lowest Price
￥19,796
Highest Price
￥976,946