Discover Your Perfect Cortona Vacation Homes

Why Choose Rent By Owner for your Cortona Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Cortona Vacation Rentals

Where are the best neighborhoods to stay in Cortona?

Choosing the right neighborhood in Cortona, Tuscany can greatly enhance your experience of this charming Italian town. Whether you prefer staying within the historic center, surrounded by centuries of art and architecture, or in a quieter area offering scenic views and tranquility, Cortona offers a variety of neighborhoods to suit your preferences. Each neighborhood provides easy access to local cafes, markets, and authentic Tuscan culture, making your stay both convenient and immersive. By selecting the ideal location within Cortona, you ensure a memorable visit to this picturesque corner of Tuscany.

Cortona Old Town

Staying within the historic core of Cortona offers you a chance to immerse yourself in the region’s rich heritage and charming ambiance. Here, you can enjoy convenient access to local shops and authentic Tuscan cuisine, making it an ideal choice for exploring this picturesque destination.

View 1103+ Rentals in Cortona Old Town

Best Times to Visit Cortona

When should you plan your Vacation Rentals stay?

Picking the ideal time to visit depends on when you want to experience the region’s picturesque landscapes and vibrant local traditions, ensuring your stay here is both memorable and relaxed.

Peak Season Highlights

spring
May to June

During late spring to early summer, the area enjoys warm weather and blossoming landscapes, making it an ideal time to explore your vacation rentals in this region.

Average Temperature Daytime: 22-27°C - Nighttime: 12-16°C
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September to October

Early fall offers pleasant temperatures and fewer crowds, allowing you to fully immerse yourself in the beauty of this destination while enjoying comfortable conditions for outdoor activities.

Average Temperature Daytime: 20-25°C - Nighttime: 10-14°C

Off-Season Highlights

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January to February

In the quiet winter months, you can find tranquility and lower rates on vacation rentals, perfect for those seeking a peaceful retreat in the area.

Average Temperature Daytime: 8-12°C - Nighttime: 1-4°C
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November to December

Late autumn to early winter is characterized by cooler temperatures and fewer tourists, offering a more relaxed experience while still enjoying the region's charm.

Average Temperature Daytime: 10-15°C - Nighttime: 3-7°C

Weekly Weather Forecast for Cortona

How to Book Your Cortona Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Cortona

More Top-Rated Vacation Rentals in Cortona Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor dining area to savor authentic Tuscan cuisine under the sun.
  • Relax on spacious terraces or patios with stunning views of the rolling countryside.
  • Make use of well-maintained swimming pools to cool off during warm summer days.
  • Take advantage of lush garden areas perfect for leisurely strolls and outdoor relaxation.
  • Utilize outdoor furniture such as loungers and shaded pergolas for comfort and convenience.
  • Experience the charm of scenic courtyards that provide a tranquil setting for outdoor gatherings.
  • Benefit from designated barbecue areas ideal for hosting outdoor cookouts in this picturesque region.

Top Attractions Around Cortona

What attractions are nearby?

In this charming region, you can explore scenic countryside walks, indulge in local culinary experiences, or visit historic sites, all just a short distance from your ideal vacation rental here in Cortona, Tuscany.

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Family Activities

  • Visit the Etruscan Academy Museum of Cortona: Explore fascinating archaeological exhibits that bring the region’s ancient history to life, perfect for engaging family members of all ages.
  • Enjoy outdoor activities at Lake Trasimeno: Spend a day relaxing by the serene waters, where you can have picnics, paddle boating, or simply enjoy the scenic views that surround this popular destination.
  • Explore local farms and vineyards: Take family-friendly tours to learn about traditional Tuscan agriculture and savor fresh produce in a charming countryside setting.
  • Discover historic streets and piazzas: Wander through charming old town areas, discovering unique shops, artisan boutiques, and lively public squares ideal for leisurely family strolls.
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Adult Activities

  • Wine Tasting Tours: Indulge in wine tasting experiences at local wineries to savor the renowned Tuscan wines while enjoying scenic views of the surrounding countryside.
  • Cooking Classes: Participate in authentic Tuscan cooking classes to learn how to create traditional dishes using fresh regional ingredients.
  • Historical and Cultural Sightseeing: Explore the rich history and art of the area through visits to historic landmarks, museums, and charming medieval streets.
  • Nature and Hiking Adventures: Discover the stunning landscapes with guided hikes or leisurely walks that showcase the region’s natural beauty.

Other Places to Stay in Cortona

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Pergo
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Cortona Old Town
Cortona Old Town Vacation Rentals
Portole
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Montalla
Montalla Vacation Rentals
Fratticciola
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San Pietro a Cegliolo
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Sodo
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Il Borgo
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Camucia
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Ossaia
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Cortona Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local cuisine: Take time to indulge in authentic Tuscan dishes at nearby eateries that highlight the region's rich culinary traditions.
  • Visit the scenic viewpoints: Make sure to seek out the breathtaking vistas and panoramic spots that offer stunning views of the surrounding countryside.
  • Discover historic sites: Immerse yourself in the area's heritage by exploring charming streets, ancient architecture, and cultural landmarks.
  • Plan leisurely outings: Allow ample time for relaxing strolls through quaint neighborhoods or peaceful afternoons at local cafés to truly enjoy your stay here.

Transportation Options

  • Car Rental Services: Renting a car gives you the flexibility to explore the area and nearby Tuscan towns at your own pace while staying connected with this charming destination.
  • Bus Services: Local buses provide an economical and convenient way to travel around here, connecting you to key points within the region without the hassle of driving.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options are readily available for quick, reliable transportation when you want to navigate the area comfortably and efficiently.
  • Private Transfers: Booking private transfers ensures a seamless arrival and departure experience, making it easier to reach your vacation rental in this scenic part of Tuscany.

Local Customs Options

  • Local Festivals and Traditions: Participating in the region’s vibrant festivals offers a wonderful way to experience authentic Tuscan culture during your stay.
  • Gastronomic Customs: Savoring traditional Tuscan dishes prepared with locally sourced ingredients reflects the area's rich culinary heritage.
  • Religious Celebrations: Attending seasonal religious events provides insight into the spiritual customs celebrated by the community year-round.
  • Artisan Craftsmanship: Visiting local workshops showcases the region’s dedication to preserving centuries-old techniques in ceramics and textiles.

Frequently Asked Questions About Cortona?

1. What are the top vacation rentals in Cortona?

There are a lot of options in Cortona. If you plan on staying in the Cortona area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cortona:

2. How many vacation rentals have private pools in Cortona?

There are 502 vacation rentals with private pools near Cortona. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cortona are best for families?

If you are looking for a family-friendly vacation home in Cortona, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cortona:

4. How many Rentbyowner vacation rentals are available in Cortona?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1721 in the Cortona area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cortona. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by listing, so it's important to review the specific terms outlined on each property’s page. Many listings offer flexible options, but details can differ, and certain restrictions may apply.

6. How do I communicate with the property owner or manager before booking?

You can send questions directly through the messaging feature on the listing page. This allows you to clarify any details regarding the property, availability, or amenities before completing your reservation.

7. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning charges, service fees, or local taxes are typically included in the total cost shown during checkout. Always review the breakdown carefully to understand what is included in your booking.

8. What amenities are commonly available in vacation rentals in this region?

Many properties feature essential amenities like Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. Specific amenities will be listed on each property page, so you can choose accommodations that suit your needs.

9. Is it possible to find pet-friendly accommodations in this destination?

Yes, there are vacation rentals that welcome pets. You can filter search results based on pet policies on the listing platform, and be sure to review any additional requirements or fees for bringing your pet along.