Best Villas in Cortona 2026

A hillside town with historic buildings, a church, and vineyards.

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Our top choices for Cortona 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

includes taxes & fees

7 Nov - 8 Nov

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

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

Cortona

includes taxes & fees

5 Dec - 6 Dec

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

3. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

includes taxes & fees

7 Nov - 8 Nov

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

4. Il Poggio dell'Eremita

Sinalunga

Paul Q.

includes taxes & fees

7 Nov - 8 Nov

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

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

Toscana

includes taxes & fees

8 Nov - 9 Nov

A stone building with a tiled roof, a paved entrance, and potted plants.

6. Antica Filanda 6 - Three Bedroom Villa, Sleeps 6

Arezzo

includes taxes & fees

8 Nov - 9 Nov

7. Godiluva, Weinvilla

Toscana

includes taxes & fees

8 Nov - 9 Nov

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

8. Villa Graziella, Romantic Perugia

La Valle

Rob B.

includes taxes & fees

7 Nov - 8 Nov

A courtyard with a pathway, a small pool, and a variety of trees and shrubs.

9. 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

includes taxes & fees

10 Nov - 11 Nov

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

10. 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.

includes taxes & fees

8 Nov - 9 Nov

A traditional stone building with a courtyard, featuring a large tree and a well-maintained garden.

11. Villa San Biagio – Luxury villa, newly renovated villa with Pool, stunning views, pool & airco

Città della Pieve

"Pros: My wife & myself loved everything about this house! From what it looked, the house has been recently fully renovated. All bedrooms are spacious & nicely decorated. There are 3 living rooms! we spent an evening playing cards in the library. The pool area is very pleasant, the view of the valley is absolutely magical! The historical village of Citta della Pieve is only 5-10 min away by car. Supermarket is close by! We will definitely stay longer next time. Cons: nothing! everything was...

Anonymous traveller

includes taxes & fees

15 Nov - 16 Nov

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

12. Wonderful villa for 4 people with WIFI, TV and terrace

Subbiano

includes taxes & fees

8 Nov - 9 Nov

A patio with a table and chairs, a large umbrella, and a vase of flowers.

13. Villa Cielo- Cignella Resort Tuscany Accommodation

Trequanda

includes taxes & fees

9 Nov - 10 Nov

A patio table with a patterned tablecloth, an umbrella, and metal chairs.

14. Villa Falco-Cignella Resort Apartments in Tuscany

Trequanda

includes taxes & fees

14 Nov - 15 Nov

A building with arched windows and a hammock in the garden.

15. Villa Aquila-Cignella Resort Acommodation Tuscany

Trequanda

includes taxes & fees

7 Nov - 8 Nov

A pool with a stone border, surrounded by a well-manicured lawn and trees.

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

Trequanda

includes taxes & fees

8 Nov - 9 Nov

A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

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

Trequanda

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio with a table, chairs, an umbrella, and a lounge chair.

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

Trequanda

includes taxes & fees

7 Nov - 8 Nov

A stone building with a tiled roof, a small porch, and a pathway leading to it.

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

San Quirico d'Orcia

includes taxes & fees

30 Nov - 1 Dec

A building with a garden, outdoor seating, and a clear sky.

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

Trequanda

includes taxes & fees

10 Nov - 11 Nov

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Top Cortona Hotel Reviews

Il Falconiere - Relais e Chateaux

10/10 Excellent

"The property was beautiful and convenient to the train station. Our suite was spacious and clean. The staff were amazing and made our stay memorable. A daily highlight was the breakfast. Highly recommend this amazing property."

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"The host was very nice and met us at the property. She gave us a tour of the apartment and explained everything for us. She also provided some good snacks made by her mother and a bottle of wine. The location is perfect for visiting Cortana and many other small towns in the area. We had a wonderful time during our stay."

Find out more about Cortona

Cortona Villas information

Number of reviews	87
Accommodation	389 Villas
Lowest Price	£69
Highest Price	£5,219

Frequently asked questions

How much do villas in Cortona cost?

Rates for villas in Cortona range between £69 and £5,219 per night. Whatever your budget, you can find someplace that fits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Cortona?

Cortona has 389 villas to choose from. Find a stay that's right for you quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.

Why book your villa in Cortona with Expedia?

Use Expedia to find your ideal villa in Cortona. Taking the kids on holiday? Make the most of our helpful filters to search for stays with amenities like WiFi and a pool. If you need to stick to a budget, choose how much you're willing to spend and the star rating of the property. We'll help you find a perfect place that suits your taste and style.

How can I find cheap villas in Cortona?

With Expedia's filter tool, scoring cheap villas in Cortona is easy. To discover options that'll make your wallet smile, fine-tune your search by amenities, star rating and budget.

What is there to do near my villa in Cortona?

You'll find loads of impressive things to see and do in Cortona. Don't miss renowned attractions like Palazzo Comunale, Cathedral of Cortona and Santa Maria Nuova. Santa Maria delle Grazie, Museum of the Etruscan Academy and Museo Diocesano are other highlights.

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Cortona Holiday Rentals

Book Villas in Cortona on Expedia.it

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona villas

1. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

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

3. Artisti del Cavallo Tourism

4. Il Poggio dell'Eremita

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

6. Antica Filanda 6 - Three Bedroom Villa, Sleeps 6

7. Godiluva, Weinvilla

8. Villa Graziella, Romantic Perugia

9. 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

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

11. Villa San Biagio – Luxury villa, newly renovated villa with Pool, stunning views, pool & airco

12. Wonderful villa for 4 people with WIFI, TV and terrace

13. Villa Cielo- Cignella Resort Tuscany Accommodation

14. Villa Falco-Cignella Resort Apartments in Tuscany

15. Villa Aquila-Cignella Resort Acommodation Tuscany

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

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

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

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

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

Find holiday rentals that suit your style

Top Cortona Hotel Reviews

Il Falconiere - Relais e Chateaux

Find out more about Cortona

Cortona Villas information

Frequently asked questions

Explore a world of travel with Expedia