Cortona vacation rentals

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Recommended by KAYAK

Best Cortona vacation rentals

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$0 - $191$191 - $381$381 - $572$572 - $762$762+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Cortona

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Monastero San Silvestro - Cortona - Bedroom
Monastero San Silvestro
Cortona, TO, Italy
9.1Wonderful(446)
Parking
Free Wi-Fi
Pool
Pet friendly
$250+
Check availability
Villa Serena - Cortona - Outdoors view
Villa Serena
Cortona, TO, Italy
8.6Very good(24)
Parking
Free Wi-Fi
Pool
Pet friendly
$259+
Check availability
Il Nido di Cortona - Cortona - Dining room
Il Nido di Cortona
Cortona, TO, Italy
9.9Wonderful(5)
Parking
Free Wi-Fi
$123+
Check availability
Villa Augusto - Cortona - Bedroom
Villa Augusto
Cortona, TO, Italy
9.3Wonderful(212)
Parking
Free Wi-Fi
Pool
Pet friendly
$207+
Check availability
Appartamenti Belvedere - Cortona - Living room
Appartamenti Belvedere
Cortona, TO, Italy
9.2Wonderful(142)
Parking
Free Wi-Fi
$146+
Check availability
Margherita Holiday Home - Cortona - Pool
Margherita Holiday Home
Cortona, TO, Italy
9.6Wonderful(160)
Parking
Free Wi-Fi
Pool
Pet friendly
$207+
Check availability
Le Residenze Ristori - Cortona
Le Residenze Ristori
Cortona, TO, Italy
9.1Wonderful(1083)
Parking
Free Wi-Fi
$99+
Check availability
La renaia - Cortona
La renaia
Cortona, TO, Italy
9.6Wonderful(221)
Parking
Free Wi-Fi
Pool
Pet friendly
$109+
Check availability
The Small Cortona Terrace - Cortona
The Small Cortona Terrace
Cortona, TO, Italy
$114+
Check availability
Borgo In San Angelo - Cortona
Borgo In San Angelo
Cortona, TO, Italy
9.2Wonderful(51)
Parking
Free Wi-Fi
Pool
Pet friendly
$146+
Check availability
Holiday home Via Porta Montanina - Cortona
Holiday home Via Porta Montanina
Cortona, TO, Italy
Free Wi-Fi
$217+
Check availability
Agriturismo Il Torrino - Cortona
Agriturismo Il Torrino
Cortona, TO, Italy
9.6Wonderful(13)
Parking
Free Wi-Fi
Pool
Pet friendly
$247+
Check availability
Casa Quintani - Cortona
Casa Quintani
Cortona, TO, Italy
9.4Wonderful(46)
Parking
Free Wi-Fi
$123+
Check availability
Agriturismo Fattoria Podere Peciano - Cortona
Agriturismo Fattoria Podere Peciano
Cortona, TO, Italy
9.6Wonderful(216)
Parking
Free Wi-Fi
Pool
Pet friendly
$193+
Check availability
Villa Giarradea - Cortona
Villa Giarradea
Cortona, TO, Italy
8.7Very good(33)
Parking
Free Wi-Fi
Pet friendly
$138+
Check availability
Terrazza Silena, centro storico con vista Cortona! - Cortona
Terrazza Silena, centro storico con vista Cortona!
Cortona, TO, Italy
9.7Wonderful(72)
Free Wi-Fi
$147+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weekend night)

March
May
$159
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 78% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Cortona vacation rental deals

  • Vacation rentals in Cortona are around 7% cheaper than hotels on average. Search here to compare prices for all accommodation types in Cortona.
  • The best vacation rental properties in Cortona are Terrazza Silena, centro storico con vista Cortona! (9.7, 72 reviews), Margherita Holiday Home (9.6, 160), and La renaia (9.6, 221), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Cortona, you should consider visiting during the low season. The cheapest vacation homes in Cortona can be found in March and August.
  • The cheapest night for renting a vacation home in Cortona is Saturday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Cortona for 21 days.

FAQs when booking a vacation home in Cortona

  • What types of vacation rentals are available in Cortona?

    There are loads of different property types that you can make your vacation home in Cortona. You’ll find agritourism, apartments, cottages, farm stays, houses, homestays and villas.

  • What are some of the most-loved vacation rentals available in Cortona?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Agriturismo Il Torrino.

  • Are there any pet-friendly vacation rentals in Cortona?

    There are a number of dog and pet-friendly Cortona vacation rentals, with around 25% allowing you to bring your pet along with you.

  • How much is a vacation rental in Cortona for tonight?

    In the last 72 hours, users have found Cortona vacation rentals for tonight for as low as $240. Search here for similar prices

  • How can I find vacation rentals near me in Cortona?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Cortona?

Our map will help you find the perfect place to stay in Cortona by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Cortona

Cortona vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Cortona. Find cheap vacation homes to rent in Cortona. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Cortona that suits you best.

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