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

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Check prices for these dates

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

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

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is CA $8,514
CA $8,514 total
includes taxes & fees
Oct 27 - Oct 28
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
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

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
Cortona
The price is CA $2,824
CA $2,855 total
includes taxes & fees
Oct 27 - Oct 28
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
A two-story building with balconies, outdoor seating, and potted plants.

3. 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 CA $109
CA $126 total
includes taxes & fees
Oct 27 - Oct 28
Artisti del Cavallo Tourism
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

4. 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 CA $218
CA $249 total
includes taxes & fees
Oct 27 - Oct 28
Il Poggio dell'Eremita
A two-story building with a balcony, outdoor seating area, and string lights.

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

VILLA IL MATTO with a saltwater pool, spa, and sauna
Toscana
The price is CA $452
CA $897 total
includes taxes & fees
Oct 27 - Oct 28
VILLA IL MATTO with a saltwater pool, spa, and sauna
Terrace/patio

6. Godiluva, Weinvilla

Godiluva, Weinvilla
Toscana
The price is CA $4,706
CA $5,870 total
includes taxes & fees
Oct 30 - Oct 31
Godiluva, Weinvilla
A terrace with a table and chairs, a view of the sunset, and a stone building.

7. 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 CA $179
CA $308 total
includes taxes & fees
Oct 27 - Oct 28
Villa Graziella, Romantic Perugia
A stone building with a swimming pool, surrounded by trees and a view of distant hills.

8. 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 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 CA $3,182
CA $3,185 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $302
CA $369 total
includes taxes & fees
Nov 2 - Nov 3
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 stone building with a central tower, surrounded by a well-maintained lawn and trees.

11. Beautiful villa for 4 guests with WIFI, TV and terrace

Beautiful villa for 4 guests with WIFI, TV and terrace
Subbiano
The price is CA $215
CA $278 total
includes taxes & fees
Oct 28 - Oct 29
Beautiful villa for 4 guests with WIFI, TV and terrace
A patio table with a patterned tablecloth, an umbrella, and metal chairs.

12. Villa Falco-Cignella Resort Apartments in Tuscany

Villa Falco-Cignella Resort Apartments in Tuscany
Trequanda
The price is CA $445
CA $450 total
includes taxes & fees
Oct 27 - Oct 28
Villa Falco-Cignella Resort Apartments in Tuscany
A patio with a table and chairs, a large umbrella, and a vase of flowers.

13. Villa Cielo- Cignella Resort Tuscany Accommodation

Villa Cielo- Cignella Resort Tuscany Accommodation
Trequanda
The price is CA $449
CA $454 total
includes taxes & fees
Oct 27 - Oct 28
Villa Cielo- Cignella Resort Tuscany Accommodation
A traditional stone building with a courtyard, featuring a large tree and a well-maintained garden.

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

Villa San Biagio – Luxury villa, newly renovated villa with Pool, stunning views, pool & airco
Città della Pieve
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Anonymous traveller
The price is CA $1,835
CA $2,155 total
includes taxes & fees
Oct 27 - Oct 28
Villa San Biagio – Luxury villa, newly renovated villa with Pool, stunning views, pool & airco
A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

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

Red Heart - Relax with Your Loved Ones in Tuscany
Trequanda
The price is CA $776
CA $1,340 total
includes taxes & fees
Oct 27 - Oct 28
Red Heart - Relax with Your Loved Ones in Tuscany
A building with a red facade, green shutters, and a tiled roof.

16. 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 CA $875
CA $880 total
includes taxes & fees
Oct 27 - Oct 28
Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & 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 CA $749
CA $754 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $875
CA $880 total
includes taxes & fees
Oct 27 - Oct 28
Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi
A stone-walled patio with wicker furniture, a table, and a view of a green landscape.

19. Wp Relais Villa Vignalunga

Wp Relais Villa Vignalunga
CASTIGLIONE D'ORCIA (SI)
10.0 out of 10, Exceptional, (58 reviews)
"If you are using google maps it is a bit hard to find the property... get directions from you phone. You will also want to have a vehicle with high clearance because you will need to go up and down dirt roads. This being said the Villa is amazing! The grounds is beautifully maintained and the layout is amazing. I highly recommend getting a meal prepared by Valentina (in-villa chef). The only thing that left us unhappy was that the dryer was down and we had to go to a laundrymat nearby. Not a...
United States
Betty
The price is CA $880
CA $1,012 total
includes taxes & fees
Nov 2 - Nov 3
Wp Relais Villa Vignalunga
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 Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Beautiful historic property well located with just enough to do. Very relaxing ."
Peter 4-night trip
Posted 10 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Cortona Villas information

Number of reviews
145
Accommodation
395 Villas
Lowest Price
CA $126
Highest Price
CA $8,514

Frequently asked questions

How much do villas in Cortona cost?
Rates for villas in Cortona range between CA $126 and CA $8,514 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 395 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 vacation? 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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