Castiglion Fiorentino Villas from AED 337

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Cortona

AED 25,634 total

includes taxes & fees

2 Nov - 3 Nov

A two-story building with a balcony, outdoor seating area, and string lights.

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

Toscana

AED 2,213 total

includes taxes & fees

2 Nov - 3 Nov

A white building with a gravel driveway, a stone wall, and a yellow umbrella.

3. Villa Serena 6 beds

Cortona

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

4. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

AED 337 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Cortona

AED 7,460 total

includes taxes & fees

2 Nov - 3 Nov

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

6. Il Poggio dell'Eremita

Sinalunga

Paul Q.

AED 626 total

includes taxes & fees

6 Nov - 7 Nov

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

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

Torrita di Siena

"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."

Nate D.

AED 9,247 total

includes taxes & fees

24 Nov - 25 Nov

A stone building with a central tower, surrounded by a well-maintained lawn and trees.

8. Stunning villa for 4 guests with WIFI, TV and terrace

Subbiano

AED 768 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Castiglion Fiorentino Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Relaxing property!"

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!"

Explore a world of travel with Expedia

Castiglion Fiorentino Vacations

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castiglion Fiorentino villas

1. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34