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Holiday homes & rentals in Cortona

Find 2,982 available offers from 72 partners
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Top 15 Recommended holiday lettings in Cortona

Find your perfect holiday home, apartment or cottage in Cortona from just £45 per night!

Villa Cortona
Villa ∙ 12 guests ∙ 5 bedrooms

Villa with garden, terrace & BBQ

Cortona, Province of Arezzo, Italy
from £174
per night
Outstanding(23 ratings)
from £174
per night
View deal
Farmhouse Cortona
Farmhouse ∙ 6 guests ∙ 2 bedrooms

Farm with garden, pool & barbecue | Panoramic view

Cortona, Province of Arezzo, Italy
This farmhouse in Cortona features a pool, kitchen, and pet-friendly spaces, perfect for family gatherings and events.
from £109
per night
from £109
per night
View deal
Villa Cegliolo
Villa ∙ 5 guests ∙ 2 bedrooms

Family-oriented villa with garden, BBQ & private pool | Pet-friendly

Cegliolo, Cortona, Italy
This villa in Cegliolo features a private pool, garden, and space for events, making it perfect for family getaways with pets.
from £104
per night
Excellent(35 ratings)
from £104
per night
View deal
Villa Cortona
Villa ∙ 5 guests ∙ 2 bedrooms

Villa with terrace, garden & barbecue

Cortona, Province of Arezzo, Italy
This villa in Cortona features a pool, fireplace, and kitchen, perfect for a getaway with pets and parking for your convenience.
from £134
per night
Outstanding(52 ratings)
from £134
per night
View deal
House Fossa del Lupo
House ∙ 6 guests ∙ 3 bedrooms

House with garden, terrace & pool

Fossa del Lupo, Cortona, Italy
This house rental in Fossa del Lupo offers a pool, garden, and fireplace, perfect for a memorable getaway with pets allowed.
from £101
per night
Excellent(53 ratings)
from £101
per night
View deal
Apartment Cortona
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat with pool | Nature view

Cortona, Province of Arezzo, Italy
This apartment in Cortona offers a pool, fireplace, kitchen, and parking, perfect for a memorable stay with pets.
from £54
per night
Outstanding(9 ratings)
from £54
per night
View deal
Apartment Cortona
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with garden, barbecue & terrace

Cortona, Province of Arezzo, Italy
This family-friendly apartment in Cortona features a pool, fireplace, garden, and parking, perfect for a memorable getaway.
from £128
per night
Good(2 ratings)
from £128
per night
View deal
Villa Cortona
Villa ∙ 4 guests ∙ 1 bedroom

Children-friendly lovely villa with barbecue, jacuzzi & private pool

Cortona, Province of Arezzo, Italy
This villa in Cortona features a private pool, fireplace, and ample space, perfect for family gatherings and events.
from £125
per night
Excellent(23 ratings)
from £125
per night
View deal
House Cortona
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbecue, private pool & garden

Cortona, Province of Arezzo, Italy
This house rental in Cortona features a private pool, garden, and balcony, accommodating up to 8 guests and pets.
from £136
per night
Outstanding(2 ratings)
from £136
per night
View deal
Maisonette Cortona
Maisonette ∙ 6 guests ∙ 3 bedrooms

Child-friendly wonderful duplex with terrace, barbeque & pool | Panoramic view

Cortona, Province of Arezzo, Italy
This duplex in Cortona features a pool, fireplace, and kitchen, perfect for a family getaway with parking for your convenience.
from £114
per night
Outstanding(22 ratings)
from £114
per night
View deal
House Cortona
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house with barbeque, private pool & garden

Cortona, Province of Arezzo, Italy
This house rental in Cortona features a private pool, spa, and fireplace, perfect for a memorable getaway with family or friends.
from £106
per night
Very good(6 ratings)
from £106
per night
View deal
Villa Cortona
Villa ∙ 16 guests ∙ 7 bedrooms

Villa with private pool, garden & terrace | Suitable for remote work

Cortona, Province of Arezzo, Italy
This villa in Cortona features a pool, fireplace, and kitchen, perfect for gatherings of up to 16 with pets welcome.
from £269
per night
Outstanding(35 ratings)
from £269
per night
View deal
House Cortona
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with terrace, barbecue & private pool

Cortona, Province of Arezzo, Italy
This house rental in Cortona features a private pool, fireplace, and kitchen, offering a perfect getaway for six guests and pets.
£161 from £151
per night
Excellent(41 ratings)
£161 from £151
per night
View deal
Villa Cortona
Villa ∙ 8 guests ∙ 4 bedrooms

Family-friendly villa with terrace, private pool & barbeque | Dogs allowed

Cortona, Province of Arezzo, Italy
This villa in Cortona features a private pool, garden, and kitchen, perfect for families and pets, accommodating up to 8 guests.
from £196
per night
Outstanding(32 ratings)
from £196
per night
View deal
House Fossa del Lupo
House ∙ 6 guests ∙ 3 bedrooms

House with pool, terrace & garden

Fossa del Lupo, Cortona, Italy
This house rental in Fossa del Lupo features a pool, fireplace, and garden, perfect for a relaxing getaway with pets.
from £104
per night
Excellent(25 ratings)
from £104
per night
View deal

Holiday homes and cottages with a garden

House  Cortona
from £208 per night
House ∙ 8 guests ∙ 4 bedrooms

Lovely holiday home with barbeque, garden & private pool | Pet-friendly

5.0
Outstanding(5 ratings)
Cortona, Province of Arezzo, Italy
Garden
View deal
Villa  Cortona
-5%
£275
from £261 per night
Villa ∙ 16 guests ∙ 7 bedrooms

Villa with garden, terrace & private pool | Perfect for remote work

4.8
Outstanding(35 ratings)
Cortona, Province of Arezzo, Italy
Garden
View deal
Villa  Cegliolo
from £107 per night
Villa ∙ 5 guests ∙ 2 bedrooms

Pleasant villa with private pool, BBQ & garden | Dogs allowed

4.5
Excellent(35 ratings)
Cegliolo, Cortona, Italy
Garden
View deal
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Holiday lettings and apartments with air conditioning

House  Cortona
from £123 per night
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped wonderful house with garden & private pool | Nature view | Dogs allowed

4.7
Excellent(20 ratings)
Cortona, Province of Arezzo, Italy
Air conditioning
View deal
Villa  Cortona
-7%
£139
from £129 per night
Villa ∙ 5 guests ∙ 2 bedrooms

Family-friendly villa with private pool, terrace & barbeque | Pets allowed

5.0
Outstanding(52 ratings)
Cortona, Province of Arezzo, Italy
Air conditioning
View deal
Villa  Cortona
from £170 per night
Villa ∙ 12 guests ∙ 5 bedrooms

Child-friendly villa with terrace, barbecue & private pool | Pets allowed

5.0
Outstanding(23 ratings)
Cortona, Province of Arezzo, Italy
Air conditioning
View deal
See all offers

Best holiday homes with a patio or terrace

Farmhouse  Cortona
from £550 per night
Farmhouse ∙ 18 guests ∙ 9 bedrooms

Farm with private pool, barbeque & garden

5.0
Outstanding(3 ratings)
Cortona, Province of Arezzo, Italy
Balcony/Patio
View deal
Villa  Cortona
from £173 per night
Villa ∙ 9 guests ∙ 4 bedrooms

Fully equipped spacious villa with terrace, barbeque & private pool | Pet-friendly

4.6
Excellent(47 ratings)
Cortona, Province of Arezzo, Italy
Balcony/Patio
View deal
House  Cortona
from £107 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped ample holiday home with terrace, garden & barbeque | Panoramic view | Pets are welcome

4.9
Outstanding(15 ratings)
Cortona, Province of Arezzo, Italy
Balcony/Patio
View deal
See all offers

Budget-friendly Holiday Homes in Cortona

Find Fantastic yet Cheap Lettings

House Cortona
from £140 per night
House ∙ 7 guests ∙ 4 bedrooms

House with private pool, garden & BBQ

4.8
Outstanding(15 ratings)
Cortona, Province of Arezzo, Italy
View deal
Villa Cortona
from £268 per night
Villa ∙ 18 guests ∙ 9 bedrooms

Villa with garden, terrace & private pool

4.6
Excellent(29 ratings)
Cortona, Province of Arezzo, Italy
View deal
House Cortona
from £198 per night
House ∙ 20 guests ∙ 10 bedrooms

Child-friendly charming house with private pool, garden & barbeque | Nature view | Dogs allowed

4.9
Outstanding(37 ratings)
Cortona, Province of Arezzo, Italy
View deal

Top-Rated Lettings and Properties in Cortona

Book Holiday Letting Offers with the Highest User Rating

Villa Cortona
from £245 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Child-friendly villa with garden, private pool & barbeque | Mountain view | Perfect for remote work | Pets allowed

4.5
Excellent(2 ratings)
Cortona, Province of Arezzo, Italy
View deal
Villa Cortona
from £132 per night
Villa ∙ 4 guests ∙ 2 bedrooms

Child-friendly wonderful villa with BBQ, garden & private pool | Dogs allowed

5.0
Outstanding(1 rating)
Cortona, Province of Arezzo, Italy
View deal
House Cortona
from £71 per night
House ∙ 4 guests ∙ 1 bedroom

Children-friendly wonderful holiday home with garden, BBQ & private pool

4.6
Excellent(84 ratings)
Cortona, Province of Arezzo, Italy
View deal

Discover real guest reviews to help you choose the perfect stay in Cortona

How are reviews collected?
Mark B.
Guest verified by HomeToGo

Excellent spot for a whole family reunion. The traditional pizza oven and grill were a centerpiece for Al fresco dining. Cortona has some excellent restaurants as well as historic sites. Very close to Florence and Siena as well

Reviewed on 06/10/2025 | Family
House Cortona
-12%
£272
from £240 per night
House ∙ 15 guests ∙ 8 bedrooms
5.0
Outstanding(5 ratings)
Cortona, Province of Arezzo, Italy
View deal
Paweł Ł.
Guest verified by HomeToGo

We had a pleasure to stay there for almost 10 days. Stefano and his family were really helpful. Everything was prepared as it supposed to be. I highly recommend that place!

Reviewed on 18/09/2025 | Family
House Cortona
from £205 per night
House ∙ 20 guests ∙ 10 bedrooms
4.9
Outstanding(36 ratings)
Cortona, Province of Arezzo, Italy
View deal
Oliver R.
Guest verified by HomeToGo

This was excellent. A "house" which included 2x apartments, that meant 2x kitchen and 4x bathrooms. Air condition in all bedrooms, which were much appreciate. It was very clean and led up to our expectations. A very nice outdoor area with a great pool, stunning view, table tennis and pool toys. The hosts were amazing. Very welcoming and super helpful. They really made us feel at home. If we needed any information about small day trips, they wrote a very great and detailed description where to park, what to see and what to do! We can't thank them enough for our amazing stay. If you are going to Tuscany, book this amazing apartment with the best hosts we have ever tried!

Reviewed on 05/08/2025 | Family
Maisonette Fratticciola
from £124 per night
Maisonette ∙ 13 guests ∙ 4 bedrooms
5.0
Outstanding(2 ratings)
Fratticciola, Cortona, Italy
View deal
Janusz O.
Guest verified by HomeToGo

Beautiful home with great pool. Spacious, four separate apartments. We were group of 7 peopele (two families, 2+1 and 2+2). Outstanding views on mountains and forest. Nice place to sit outside. Supermarket 15 minutes by car. Helpful hosts, pool was cleaned everyday. Some cons: Not each apartment was fully equipped (kitchen equpment for example, lack of dishes etc.), some noises at night (barking dogs, there is a dog shelter nearby), the plot is not fully fenced which was a bit problematic due to our dogs. Generaly this is a great place to go. Recommended!

Reviewed on 22/08/2024 | Family
House Cortona
from £217 per night
House ∙ 10 guests ∙ 4 bedrooms
4.6
Excellent(18 ratings)
Cortona, Province of Arezzo, Italy
View deal
Sabine G.
Guest verified by HomeToGo

Wunderful scenary and house, garden and pool area lovely decorated. Owners very nice and helful. It was wonderful. However, "home to go" should inform clients that it is not suitable for elderly people. The pool can only be accessed by climbing down a hill (and it is not next to the house). Though you also do not see the pool from the house, since there is another house in between. The road to the house is pretty bad and it takes you 40 minutes to the next supermarket in Cortona. For me and my husband it was not a problem and all in all we loved it there.

Reviewed on 08/08/2024 | Family
Villa Cortona
from £513 per night
Villa ∙ 10 guests ∙ 5 bedrooms
4.8
Outstanding(5 ratings)
Cortona, Province of Arezzo, Italy
View deal
Carol H.
Guest verified by HomeToGo

Peaceful location, very clean, giada was so accomodating. She provided a menu and the food was excellent

Reviewed on 10/06/2024 | Couple
Villa Cortona
from £194 per night
Villa ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(10 ratings)
Cortona, Province of Arezzo, Italy
View deal
Elwira P.
Guest verified by HomeToGo

Great place to stay! Adorable localizarion, with comfortable access to Cortona and with great garden! Absolutely comfortable apartment: Nice bedrooms, well equipped kitchen including coffee, tea and basic ingredients for cooking and welcome fruits:) Very hospitable owner offered great service (contact before with navigation details and all additional information needed during our stay). I do recommend Robert's house - it's an excellent place.

Reviewed on 22/09/2023 | Group
Farmhouse Cortona
from £89 per night
Farmhouse ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(30 ratings)
Cortona, Province of Arezzo, Italy
View deal
Katharina H.
Guest verified by HomeToGo

Staying at this location was the perfect vacation! We were 7 young people and we had a great time. The house was clean and incredibly well equipped - we had everything we could need. The home owner was super friendly, obliging and every transaction was very uncomplicated. I can only recommend staying here. The view is breathtaking, the house and garden are beautiful and the city of Cortona is definitely worth a visit.

Reviewed on 05/09/2023 | Group
House Cortona
from £95 per night
House ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent(27 ratings)
Cortona, Province of Arezzo, Italy
View deal
Sarah L.
Guest verified by HomeToGo

A delightful place with spectacular views. The location is perfect for Cortona, walks, dining and cycle tours. The host Silvia was very responsive and friendly. There is a truly superb restaurant next door- not cheap but absolutely worth every penny for a treat. There are loads of very affordable restaurants within 10 minutes walk. There was a delicious welcome basket of essentials and drinks in the fridge and a v comfortable bed. The pool was clean and had gorgeous views (and a glass safety ‘gate’ if you’re there with kids). You can pick your fresh herbs and figs from the garden and the chef next door will bring you handfuls of freshly picked berries.

Reviewed on 12/06/2023 | Couple
House Cortona
from £153 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(4 ratings)
Cortona, Province of Arezzo, Italy
View deal
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Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Cortona

  • Pool (2,036)
  • WiFi (2,656)
  • Air conditioning (2,097)
  • TV (2,391)
  • Kitchen (2,562)
  • Washing machine (2,158)
  • Parking (436)
  • Garden (2,069)
  • Grill (1,747)
  • Balcony/patio (1,587)
  • Dishwasher (1,584)
  • Pet-friendly (1,609)

Finding a holiday rental that includes a pool shouldn't be too hard in Cortona. Many of the rentals here have one. Additionally, more apartment rental have pools than any other type of accommodation. They are an excellent choice if you go in a group of 5, as that is the number of people they can accommodate on average. If, ideally, you would like to be close to the water, more than half of the holiday rentals with a pool are located within 2 kilometres of the waterfront.

Price and Availability Index for Cortona

Click on any bar to see price and availability information

Holiday Letting Price Information in Cortona

The graph shows the average holiday rental prices for the next twelve months in Cortona. The most expensive month in Cortona is August (22/08 – 29/08), when nightly prices are £345 on average. Prices decrease in April to an average of £302 per night (11/04 – 18/04).

Rental availability information in Cortona

Have a look at the graph above to see the availability of rentals in Cortona. The week with the highest booking rate in the next 6 months is in January (16/01 – 23/01), when 95% of the holiday lettings are booked. Conversely, you will find the highest number of available rentals during one week in May (23/05 – 30/05).

Enjoy classic Tuscan living with Cortona holiday accommodation

Holiday accommodation in Cortona, Italy is all about art, culture and history. The Etruscan origins of the city are still obvious and little has changed about the bucolic cornucopia of Cortona since those days. Feast on the rich Cortonese game dishes that have been lovingly handed down the generations, along with serene yet sumptuous ambiance.

Where are the unique attractions in Cortona?

Travel in Tuscany

Don't miss the monumental stone portal to the city that has lasted since Etruscan times. The Porta Bifora transports you back in time in just a few steps.

In the area around Cortona you will find still more unmissable attractions. One such is the Medici Fortress which stands on a hill overlooking the city. It was constructed in 1561 at the behest of the supremely powerful family.

Information about holiday rentals in Cortona

🏡 Holiday homes available 2,982 rentals
🌙 Nightly prices from £45
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly rentals 1,615 properties
🏊 Holiday rentals with pools 2,070 properties
454 reviews
Cortona holiday rentals have an average rating of 4.3/5 across 454 reviews left by travellers.

Frequently Asked Questions

What is a common nightly rate for a holiday rental in Cortona?

Nightly rates for holiday rentals in Cortona start from around £45. Whether you're after something simple or more luxurious, there's a wide range available. Check HomeToGo to see current rates and discounts.

How many holiday homes are available to rent in Cortona? And what are the most popular types of holiday lets?

There are 2,982 holiday apartments in Cortona to choose from and book for your upcoming trip. One-third of holiday rentals in Cortona are villa, making them a top pick among travellers. They’re ideal whether you’re planning a romantic escape or a group getaway. HomeToGo makes it easy to find a holiday home that fits your needs.

What is the most popular holiday apartment amenity in Cortona?

The most popular amenities among our customers in Cortona are Pool, Internet and Air conditioning.

Do you offer holiday homes with a swimming pool in Cortona?

Yes, 69% of holiday lettings in Cortona include access to a swimming pool. Enjoy your own private swim spot by browsing one of the 2,070 properties with a pool available. Use the 'pool' filter on HomeToGo to see your options.

What is the best time of year to travel to Cortona?

Sun lovers should visit Cortona in July and August to enjoy the warmest weather.

Where can I see discounts on holiday homes in Cortona?

You can get brilliant bargains on holiday rentals in Cortona with prices for a letting beginning at £45 - and HomeToGo has launched plenty of filters that mean it's quick and simple to locate some awesome offers. If you don't have set dates for a trip, you can use HomeToGo's flexible dates technology to quickly locate great value date options and get discounts of as much as 6%. Furthermore, HomeToGo's 'distance from' filter can help you see hidden gem holiday homes in great value, under-the-radar spots which are still near to your desired destination, whether that's a beach, lake, ski region or city centre. Start your search as soon as possible to make the most of the greatest variety of options and top discounts - and do so without worries by using HomeToGo's 'free cancellation' filter as you look for the perfect holiday home.

What are the advantages of finding a holiday home in Cortona with HomeToGo?

From increased privacy away from the crowds to plenty of room to enjoy with your loved ones, holiday lettings in Cortona offer plenty of bonuses. HomeToGo shows you real reviews from verified visitors, and searching is secure, simple, and hassle-free - so with 2,982 lettings from 72 providers in the area, you're sure to uncover the ideal type of accommodation with all of the amenities that are important to you in Cortona.

Do you offer holiday accommodation for couples in Cortona?

There are lovely holiday homes in Cortona designed with couples in mind. Whether you’re after seclusion or a city break, there’s something for every type of trip. HomeToGo helps you discover the best spots for two.

Can I book a waterfront holiday rental in Cortona?

You can book one of 128 waterfront holiday homes in Cortona for a truly scenic break. These spots are perfect for a morning coffee with a view or lazy days by the water. Use HomeToGo’s "Near the water" filter to find your perfect waterfront holiday let.

Why should I book my holiday rental with HomeToGo?

With HomeToGo, you get access to the world’s largest selection of holiday lettings – all in one place. We compare prices across providers to help you save time and money. Book with confidence and enjoy support every step of the way.

Can I find family-friendly holiday lettings in Cortona?

Yes, there are lots of family-friendly holiday homes in Cortona. Top options can host groups of up to 10, perfect for holidays with kids or extended family. Use HomeToGo to discover the best places to stay with the whole gang.

Can I cancel my holiday rental booking for free?

Free cancellation is available on lots of holiday homes, depending on the provider. This gives you flexibility in case your travel plans change.

Is it possible to rent a holiday home for a weekend getaway in Cortona?

Yes, weekend breaks are easy to plan with flexible holiday rentals in Cortona. Many homes offer short stays without long commitments. HomeToGo helps you spot the best weekend-friendly options fast.

Are there any last-minute holiday rental deals in Cortona?

Yes, HomeToGo regularly features last-minute holiday deals in Cortona. You might even save up to 6% if you’re flexible with dates. Use HomeToGo’s filters to see what’s available right now.

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