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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Castiglion Fiorentino villas

A two-story building with balconies, outdoor seating, and potted plants.

1. 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 NZ$162
includes taxes & fees
27 Oct - 28 Oct
Artisti del Cavallo Tourism
A stone patio with two wooden lounge chairs, a small pool, and a view of the countryside.

2. Stone house villa with Spa in Cortona

Stone house villa with Spa in Cortona
Cortona Old Town
9.0 out of 10, Wonderful, (40 reviews)
"Villa Letizia is a hidden gem! The views of Lake Trasimeno are absolutely breathtaking, especially during sunset, The garden area is perfect for lounging, and the hammock was my favorite spot to unwind with a book,"
Germany
Anonymous traveller
Stone house villa with Spa in Cortona
A well-lit courtyard with a stone pathway leading to a building with a large arched entrance.

3. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is NZ$10,669
includes taxes & fees
27 Oct - 28 Oct
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
A two-story building with a balcony, outdoor seating area, and string lights.

4. VILLA IL MATTO with a saltwater pool, spa, and sauna

VILLA IL MATTO with a saltwater pool, spa, and sauna
Toscana
The price is NZ$1,085
includes taxes & fees
27 Oct - 28 Oct
VILLA IL MATTO with a saltwater pool, spa, and sauna
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 NZ$312
includes taxes & fees
27 Oct - 28 Oct
Il Poggio dell'Eremita
A stone wall, a round table with chairs, a bowl of fruit, and a glass of juice.

6. 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 NZ$3,577
includes taxes & fees
27 Oct - 28 Oct
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
A stone building with a swimming pool, surrounded by trees and a view of distant hills.

7. 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 terrace with a table and chairs, a view of the sunset, and a stone building.

8. Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (11 reviews)
"Great place. Would stay here again."
United States
Rob B.
The price is NZ$382
includes taxes & fees
27 Oct - 28 Oct
Villa Graziella, Romantic Perugia
A tree, a lamp post, and a clear blue pool with a view of distant mountains.

9. 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 NZ$3,991
includes taxes & fees
2 Nov - 3 Nov
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.

10. 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 NZ$462
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.

11. Villa Falco-Cignella Resort Apartments in Tuscany

Villa Falco-Cignella Resort Apartments in Tuscany
Trequanda
The price is NZ$564
includes taxes & fees
24 Nov - 25 Nov
Villa Falco-Cignella Resort Apartments in Tuscany
A patio with a table and chairs, a large umbrella, and a vase of flowers.

12. Villa Cielo- Cignella Resort Tuscany Accommodation

Villa Cielo- Cignella Resort Tuscany Accommodation
Trequanda
The price is NZ$569
includes taxes & fees
27 Oct - 28 Oct
Villa Cielo- Cignella Resort Tuscany Accommodation
A stone building with a staircase leading to a porch, a small adjacent structure, and a row of green folding chairs in front.

13. Villa Santarsa, sleeps 31, stunning views and a private pool, no neighbors

Villa Santarsa, sleeps 31, stunning views and a private pool, no neighbors
Sansepolcro
10.0 out of 10, Exceptional, (16 reviews)
"We had a great time, despite the heat. It's a bit of a drive up the mountain to Santarsa specifically, so make sure you have enough cars!"
United States
Donnacha F.
The price is NZ$2,710
includes taxes & fees
2 Nov - 3 Nov
Villa Santarsa, sleeps 31, stunning views and a private pool, no neighbors
A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

14. Red Heart - Relax with Your Loved Ones in Tuscany

Red Heart - Relax with Your Loved Ones in Tuscany
Trequanda
The price is NZ$1,624
includes taxes & fees
27 Oct - 28 Oct
Red Heart - Relax with Your Loved Ones in Tuscany
A building with a red facade, green shutters, and a tiled roof.

15. 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 NZ$1,103
includes taxes & fees
27 Oct - 28 Oct
Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
A stone building with a tiled roof, a small porch, and a pathway leading to it.

16. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
San Quirico d'Orcia
The price is NZ$3,493
includes taxes & fees
27 Oct - 28 Oct
Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
A building with arched windows and a hammock in the garden.

17. Villa Aquila-Cignella Resort Acommodation Tuscany

Villa Aquila-Cignella Resort Acommodation Tuscany
Trequanda
The price is NZ$944
includes taxes & fees
24 Nov - 25 Nov
Villa Aquila-Cignella Resort Acommodation Tuscany
A pool with a stone border, surrounded by a well-manicured lawn and trees.

18. 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 NZ$1,103
includes taxes & fees
27 Oct - 28 Oct
Apartment In A Hotel "Villa Cielo" 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

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa

10/10 Excellent
"Our stay at Poggio Paradiso was as lovely as we could've imagined. The staff was very attentive to every need and it felt like we were at home throughout our time on the property. The location and views are amazing and the restaurant on site was delicious for both the complimentary breakfast and convenient dinners. Would absolutely stay here again!"
Brian 3-night trip
Posted 6 hours ago
Poggio Paradiso Resort & Spa

Find out more about Castiglion Fiorentino

Castiglion Fiorentino Villas information

Number of reviews
142
Accommodation
1411 Villas
Lowest Price
NZ$162
Highest Price
NZ$10,669