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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Castiglion Fiorentino villas

A well-lit courtyard with a stone pathway leading to a building with a large arched entrance.

1. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is AED 22,353
AED 22,353 total
includes taxes & fees
21 Oct - 22 Oct
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
A two-story building with balconies, outdoor seating, and potted plants.

2. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is AED 284
AED 329 total
includes taxes & fees
23 Oct - 24 Oct
Artisti del Cavallo Tourism
A stone building with a swimming pool, surrounded by trees and a view of distant hills.

3. 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
A stone wall, a round table with chairs, a bowl of fruit, and a glass of juice.

4. Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
Cortona
The price is AED 7,413
AED 7,495 total
includes taxes & fees
21 Oct - 22 Oct
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

5. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AED 555
AED 646 total
includes taxes & fees
21 Oct - 22 Oct
Il Poggio dell'Eremita
A tree, a lamp post, and a clear blue pool with a view of distant mountains.

6. 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
10.0 out of 10, Exceptional, (1 review)
"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."
United States
Nate D.
The price is AED 8,932
AED 8,941 total
includes taxes & fees
21 Oct - 22 Oct
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

7. 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 793
AED 968 total
includes taxes & fees
2 Nov - 3 Nov
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
A patio table with a patterned tablecloth, an umbrella, and metal chairs.

8. Villa Falco-Cignella Resort Apartments in Tuscany

Villa Falco-Cignella Resort Apartments in Tuscany
Trequanda
The price is AED 1,169
AED 1,181 total
includes taxes & fees
21 Oct - 22 Oct
Villa Falco-Cignella Resort Apartments in Tuscany
A patio with a table and chairs, a large umbrella, and a vase of flowers.

9. Villa Cielo- Cignella Resort Tuscany Accommodation

Villa Cielo- Cignella Resort Tuscany Accommodation
Trequanda
The price is AED 1,180
AED 1,192 total
includes taxes & fees
24 Oct - 25 Oct
Villa Cielo- Cignella Resort Tuscany Accommodation
A stone building with a central tower, surrounded by a well-maintained lawn and trees.

10. Stunning villa for 4 people with WIFI, TV and terrace

Stunning villa for 4 people with WIFI, TV and terrace
Subbiano
The price is AED 564
AED 730 total
includes taxes & fees
22 Oct - 23 Oct
Stunning villa for 4 people with WIFI, TV and terrace
A building with a red facade, green shutters, and a tiled roof.

11. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
Trequanda
The price is AED 2,553
AED 2,566 total
includes taxes & fees
21 Oct - 22 Oct
Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
A building with arched windows and a hammock in the garden.

12. Villa Aquila-Cignella Resort Acommodation Tuscany

Villa Aquila-Cignella Resort Acommodation Tuscany
Trequanda
The price is AED 1,966
AED 1,978 total
includes taxes & fees
21 Oct - 22 Oct
Villa Aquila-Cignella Resort Acommodation Tuscany
A house with a patio, outdoor seating, and a view of the landscape.

13. 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 2,471
AED 2,483 total
includes taxes & fees
21 Oct - 22 Oct
Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
An outdoor patio with a table, chairs, an umbrella, and a lounge chair.

14. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi
Trequanda
The price is AED 2,553
AED 2,566 total
includes taxes & fees
21 Oct - 22 Oct
Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi
A building with arched windows and a hammock in the garden.

15. Apartment In A Hotel "Villa Aquila" with Shared Pool, Private Terrace & Wi-Fi

Apartment In A Hotel "Villa Aquila" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
The price is AED 3,912
AED 3,925 total
includes taxes & fees
21 Oct - 22 Oct
Apartment In A Hotel "Villa Aquila" with Shared Pool, Private Terrace & Wi-Fi
An aerial view of a property with a swimming pool, multiple small buildings, and a winding road.

16. 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 793
AED 968 total
includes taxes & fees
2 Nov - 3 Nov
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
A pool with a stone border, surrounded by a well-manicured lawn and trees.

17. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
The price is AED 2,426
AED 2,438 total
includes taxes & fees
24 Oct - 25 Oct
Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi
A two-story house with a red facade, green shutters, and a well-maintained lawn.

18. Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w
Trequanda
The price is AED 826
AED 1,008 total
includes taxes & fees
3 Nov - 4 Nov
Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w
A residential area with multiple houses, a clear sky, and a distant view of the sea.

19. Elegant and spacious two-storey villa of 156 m2 consisting of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer, internal and external dining area, a master double bedroom wit

Elegant and spacious two-storey villa of 156 m2 consisting of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer, internal and external dining area, a master double bedroom wit
Trequanda
The price is AED 959
AED 1,169 total
includes taxes & fees
8 Nov - 9 Nov
Elegant and spacious two-storey villa of 156 m2 consisting of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer, internal and external dining area, a master double bedroom wit
A building with a red facade, arched doorways, and a patio area with outdoor seating.

20. Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi

Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
The price is AED 2,553
AED 2,566 total
includes taxes & fees
22 Oct - 23 Oct
Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi
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

Relais Cloister Pienza

Relais Cloister Pienza

10/10 Excellent
"An Incredible Terrace with the Most Amazing Views! ⭐⭐⭐⭐⭐ The hotel is beautifully restored and in a fantastic location in Pienza, just off Piazza Pio II. Our room was spotlessly clean, comfortable, with good bedding and a lovely large bathroom. The room itself was simple but very comfortable and had everything we needed. However, the absolute highlight of this hotel is the terrace. The views across the Val d’Orcia are quite simply out of this world! You could sit there for hours just taking it all in. We honestly think it must be the best spot in the whole of Pienza to enjoy those incredible Tuscan views. The staff were attentive and welcoming, and breakfast was also good. We would highly recommend staying here, especially for the terrace. If you want to experience the beauty of Tuscany from a truly breathtaking viewpoint, this is the place to stay!"
Jane 1-night trip
Posted 9 hours ago
Relais Cloister Pienza

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