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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Castelfalfi villas

Exterior
Villa Cattleya

Villa Cattleya

Villa Cattleya
Casciana Terme
10.0 out of 10, Exceptional, (1)
"Tout était impeccable. "
France
Stéphane S.
The price is AED 387
AED 542 total
includes taxes & fees
4 Jan - 5 January 2026
Villa Cattleya
Pool
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

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)
"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 AED 6,967
AED 6,976 total
includes taxes & fees
6 Jan - 7 January 2026
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is AED 50,750
AED 50,750 total
includes taxes & fees
26 Dec - 27 Dec
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Exterior
Villa 'Sunflowers' with Mountain View, Wi-Fi and Air Conditioning

Villa 'Sunflowers' with Mountain View, Wi-Fi and Air Conditioning

Villa 'Sunflowers' with Mountain View, Wi-Fi and Air Conditioning
Cascina
The price is AED 538
AED 860 total
includes taxes & fees
7 Jan - 8 January 2026
Villa 'Sunflowers' with Mountain View, Wi-Fi and Air Conditioning
Pool
Villa Altea - Homelike Villas

Villa Altea - Homelike Villas

Villa Altea - Homelike Villas
Lajatico
10.0 out of 10, Exceptional, (1)
"Wir hatten eine wunderschöne Woche in einem tollen Haus und mit einem sehr aufmerksamen Gastgeber, danke Riccardo! Die Kommunikation mit der Agentur (Home Villas) war unterirdisch!!! Auf keine Email kam eine Reaktion, außer dass man sich melden würde. Wir wollten vorab einige Dinge abklären (Anzahl der Personen hatte sich reduziert, wäre früherer Check In möglich, etc.), selbst das vorzeitige Anmelden aller Personen mit Ausweisen wurde nicht an den Vermieter weitergeleitet!! Vor Ort gab es...
Germany
Stephan H.
Villa Altea - Homelike Villas
Exterior
Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AED 19,973
AED 21,568 total
includes taxes & fees
5 Jan - 6 January 2026
Villa "Arnilù" with Private Pool & Wi-Fi
Pool
"A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1)
"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 AED 3,199
AED 4,786 total
includes taxes & fees
23 Dec - 24 Dec
"A Casa di Franca Villa con piscina"
Outdoor pool
Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (6)
"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"
United States
Frank V.
The price is AED 3,097
AED 5,505 total
includes taxes & fees
3 Jan - 4 January 2026
Beautiful Tuscan home between Florence & Siena
Exterior
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Montespertoli
10.0 out of 10, Exceptional, (12)
"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 AED 5,505
AED 6,305 total
includes taxes & fees
7 Jan - 8 January 2026
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Exterior
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is AED 5,591
AED 6,404 total
includes taxes & fees
7 Jan - 8 January 2026
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Exterior detail
Villa Franco

Villa Franco

Villa Franco
Castelfranco di Sotto
The price is AED 1,290
AED 2,254 total
includes taxes & fees
23 Dec - 24 Dec
Villa Franco
Pool
Villa Fiordaliso - Homelike Villas

Villa Fiordaliso - Homelike Villas

Villa Fiordaliso - Homelike Villas
Lajatico
Villa Fiordaliso - Homelike Villas
Room | Terrace/patio
Villa Tosca

Villa Tosca

Villa Tosca
Peccioli
The price is AED 5,978
AED 6,576 total
includes taxes & fees
3 Jan - 4 January 2026
Villa Tosca
Terrace/patio
Antico Borghetto di Tigliano Cozy and ideal for families with children

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 AED 1,761
AED 2,273 total
includes taxes & fees
26 Dec - 27 Dec
Antico Borghetto di Tigliano Cozy and ideal for families with children
Pool
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Tavarnelle Val di Pesa
The price is AED 5,098
AED 6,252 total
includes taxes & fees
23 Dec - 24 Dec
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
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 Castelfalfi Hotel Reviews

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
Allyson 3-night trip
Posted 3 weeks ago
Hotel Borgo San Luigi