A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Castiglion Fiorentino villas

Outdoor dining

Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (9 reviews)
"Great place. Would stay here again."
United States
Rob B.
The price is AED 670
AED 1,006 total
includes taxes & fees
24 Jul - 25 Jul
Villa Graziella, Romantic Perugia
Exterior

Panoramic country Villa 6/8 people in Tuscany, bbq wood-fired oven, heating, A/C

Panoramic country Villa 6/8 people in Tuscany, bbq wood-fired oven, heating, A/C
Sarteano
The price is AED 605
AED 706 total
includes taxes & fees
1 Aug - 2 Aug
Panoramic country Villa 6/8 people in Tuscany, bbq wood-fired oven, heating, A/C
Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (68 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
Il Poggio dell'Eremita
Exterior

Beautiful Villa in a peaceful place, ideal for family holidays.

Beautiful Villa in a peaceful place, ideal for family holidays.
Umbertide
10.0 out of 10, Exceptional, (12 reviews)
"A wonderful villa with magnificent view - the photos don't do it justice. Great to get away from life for a week, enjoy the garden and pool, and see local area. Note it's a 15 min drive to the nearest road junction - but for us part of the charm and location."
United Kingdom
Neil C.
The price is AED 2,461
AED 2,765 total
includes taxes & fees
2 Aug - 3 Aug
Beautiful Villa in a peaceful place, ideal for family holidays.
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is AED 287
AED 324 total
includes taxes & fees
7 Aug - 8 Aug
Artisti del Cavallo Tourism
Exterior

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
Trequanda
The price is AED 1,091
AED 1,332 total
includes taxes & fees
8 Aug - 9 Aug
Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
Pool

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is AED 1,589
AED 1,769 total
includes taxes & fees
19 Jul - 20 Jul
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Outdoor dining

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Wunderschönes charmantes, rustikales Ferienhaus in der wunderschönen Toskana. Tolle Lage, sehr freundlicher und charmanter Gastgeber. Senore Guidi und seine Ehefrau sind zauberhafte Gastgeber. Sehr hilfsbereit und zuvorkommend! Die Fotos der Unterkunft stimmen zu 100% überein! Toller Poolbereich. Senor Guidi hat zur Wein- und Olivenöl -Verkostung eingeladen und uns auf Anfrage zu einer persönlichen Begehung seiner Oliven-und-Weinberge mitgenommen. Sehr persönliche und menschliche...
Germany
Anonymous traveler
The price is AED 1,757
AED 1,938 total
includes taxes & fees
18 Jul - 19 Jul
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Pool

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is AED 2,774
AED 2,955 total
includes taxes & fees
9 Aug - 10 Aug
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Exterior

Casale Le Rondini with a swimming pool and private garden

Casale Le Rondini with a swimming pool and private garden
LUCIGNANO
Casale Le Rondini with a swimming pool and private garden
Pool

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Torrita di Siena
The price is AED 13,731
AED 13,740 total
includes taxes & fees
20 Jul - 21 Jul
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Exterior

Villa "Il Rancho Grande" with Private Pool, Private Terrace & Wi-Fi

Villa "Il Rancho Grande" with Private Pool, Private Terrace & Wi-Fi
Città di Castello
10.0 out of 10, Exceptional, (1 review)
"Pros: Mi è piaciuto tutto"
Italy
Anonymous traveler
The price is AED 4,060
AED 4,581 total
includes taxes & fees
19 Jul - 20 Jul
Villa "Il Rancho Grande" with Private Pool, Private Terrace & Wi-Fi
Outdoor dining

Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria
Lisciano Niccone
The price is AED 12,621
AED 12,629 total
includes taxes & fees
24 Jul - 25 Jul
Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is AED 3,075
AED 4,117 total
includes taxes & fees
18 Jul - 19 Jul
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Property grounds

Villa I Girasoli in Montepulciano with Swimming pool

Villa I Girasoli in Montepulciano with Swimming pool
Montepulciano
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay at the villa. Alex and Gabrielle were very helpful before and during our stay, answering all our questions and being very responsive. The view out our front window was incredible along with the front porch and pool overlooking their vineyard and rolling hills. The house was perfect for our needs. Very clean, well kept, and an authentic Tuscan villa experience. And, their own wine is fabulous!"
United States
Julie V.
The price is AED 2,774
AED 2,774 total
includes taxes & fees
12 Aug - 13 Aug
Villa I Girasoli in Montepulciano with Swimming pool
Exterior

Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.
Trequanda
Red Heart - relax with those you love in Tuscany.
Exterior

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
The price is AED 4,152
AED 4,327 total
includes taxes & fees
31 Jul - 1 Aug
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Terrace/patio

Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi

Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
The price is AED 3,622
AED 3,635 total
includes taxes & fees
8 Aug - 9 Aug
Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
Exterior

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Cortona
10.0 out of 10, Exceptional, (28 reviews)
"Great location with gorgeous views over the Chiana hills, and nearby restaurants. We enjoyed discovering Cortona and several hill towns in the ares"
United States
Patricia H.
The price is AED 2,128
AED 2,435 total
includes taxes & fees
11 Aug - 12 Aug
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Exterior

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is AED 20,532
AED 20,532 total
includes taxes & fees
18 Jul - 19 Jul
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
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 Castiglion Fiorentino Hotel Reviews

Villa Svetoni Wine Resort

Villa Svetoni Wine Resort

10/10 Excellent
"Other than the fact that the bathroom was unbearably hot (no AC), we had a wonderful stay!"
Katie 1-night trip
Posted less than an hour ago
Villa Svetoni Wine Resort