- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
Why Choose Rent By Owner for your Cortona Family Rental?
What makes our Family Rental special?
Popular Areas for Cortona Family Rental
Where are the best neighborhoods to stay in Cortona?
Choosing a neighborhood in Cortona, Tuscany, allows you to immerse yourself in authentic Italian charm while enjoying convenient access to local amenities. Historic areas offer picturesque streets and stunning views that perfect family rentals, providing an ideal base for exploring the region's rich cultural heritage. Whether you prefer a lively center or a peaceful outskirts, each neighborhood provides a welcoming environment for your family getaway.
Cortona Old Town
Staying in the historic heart of this destination offers you charming streets and authentic Tuscan ambiance, perfect for exploring local culture and enjoying picturesque views. Here, your family can experience an immersive stay surrounded by timeless architecture and welcoming community vibes.
View 740+ Rentals in Cortona Old TownBest Times to Visit Cortona
When should you plan your Family Rental stay?
Choosing the right time to vacation here ensures you experience the region's beauty and tranquility at its best, making your stay in this destination truly memorable and perfect for relaxing with family.
Peak Season Highlights
Spring (April to June)
During spring, the region blossoms with vibrant landscapes and pleasant weather, making it an ideal time to explore this destination with your family. The warm days and mild evenings create a comfortable environment for outdoor activities.
Fall (September to October)
Early fall offers favorable weather and fewer crowds, allowing you to enjoy the area's scenic beauty and cultural events with your loved ones. Temperatures remain warm during the day while evenings become cooler, perfect for cozy evenings in your rental.
Off-Season Highlights
Winter (November to February)
The quieter winter months provide a peaceful atmosphere, ideal for families seeking a more relaxed stay. While temperatures are cooler, the region's charm remains, and you can experience a serene escape here.
Late Spring/Early Summer (May to June before peak) or Late Fall (November)
These shoulder months often see fewer visitors, offering more affordable rates and less crowded attractions, suitable for families looking for a tranquil getaway in this picturesque area.
Weekly Weather Forecast for Cortona
How to Book Your Cortona Family Rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Common Family Rental Amenities
What amenities can you expect?
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
- Relax in a private outdoor seating area with scenic views of the Tuscan countryside.
- Enjoy a communal swimming pool surrounded by lush greenery and open space.
- Take advantage of well-maintained gardens perfect for family picnics and outdoor activities.
- Utilize outdoor dining spaces ideal for savoring authentic regional cuisine al fresco.
- Explore walking or biking paths that wind through the picturesque landscape of the region.
- Make use of spacious terraces or patios for outdoor lounging and gatherings.
- Benefit from access to landscaped courtyards that add to the charm and privacy of your stay.
Top Attractions Around Cortona
What attractions are nearby?
Within this charming region, you can enjoy exploring scenic walking trails, visiting historic sites, and experiencing local wineries-all easily accessible from your family rental here in Cortona, Tuscany, Italy, offering a perfect blend of cultural immersion and outdoor activities for the whole family to enjoy.
Family Activities
- Visit the Etruscan Academy Museum of Cortona: Discover fascinating archaeological exhibits that engage children and offer a glimpse into the area's ancient history.
- Explore the historic town center of Cortona: Wander through charming streets and alleys, enjoying stunning views and family-friendly cafes along the way.
- Enjoy outdoor activities in the surrounding countryside: Participate in scenic walks or picnics that allow your family to experience the natural beauty of this region.
- Attend local cultural events and festivals: Experience the vibrant traditions and lively atmosphere that bring families together in this authentic destination.
Adult Activities
- Wine Tasting Tours: Discover the region's renowned wine cellars and savor local vintages that showcase the area's rich winemaking heritage.
- Cooking Classes: Enhance your culinary skills with authentic Tuscan cooking experiences that highlight the region’s traditional flavors and ingredients.
- Historical Sightseeing: Explore ancient churches, medieval streets, and significant landmarks that tell the story of this charming destination.
- Art and Culture Experiences: Visit art galleries and participate in cultural workshops to immerse yourself in the artistic spirit that defines the region.
Other Places to Stay in Cortona
Fossa del Lupo
Montalla
Il Borgo
Ossaia
Cortona Old Town
Portole
Fratticciola
Mercatale di Cortona
San Pietro a Cegliolo
Camucia
Cortona Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Make sure to indulge in authentic Tuscan dishes at local eateries to truly experience the region’s culinary heritage.
- Visit Cultural Sites: Take time to tour the historic landmarks and museums that showcase the rich history and art of this captivating destination.
- Enjoy Scenic Walks: Wander through charming streets and scenic countryside paths to immerse yourself in the area's natural beauty and relax in a peaceful setting.
- Plan Day Trips: Use your stay as a base to explore nearby towns and attractions, allowing you to maximize your experience of the broader region.
Transportation Options
- Rental Cars: Renting a car offers the flexibility to explore the picturesque countryside and nearby towns at your own pace, making it an ideal choice for families staying in this charming region.
- Public Buses: The local bus services connect you conveniently to nearby cities and attractions, providing an affordable transportation option for exploring the area without the hassle of driving.
- taxis and Rideshare Services: Taxis and ride-hailing options are widely available here, offering quick and comfortable transfers for family outings and day trips within the region.
- Walking and Biking: For those who prefer a more active approach, walking and biking paths allow you to enjoy the scenic beauty of this destination firsthand while easily accessing nearby amenities.
Local Customs Options
- La Passeggiata: Taking a leisurely evening stroll, known locally as "la passeggiata," is a cherished tradition here, allowing you to enjoy the charming streets and social atmosphere.
- Local Food and Wine Etiquette: When dining in this region, it’s customary to greet your hosts politely and appreciate the traditional Tuscan cuisine and regional wines with respect.
- Festivals and Religious Celebrations: Participating in seasonal festivals and religious processions offers insight into the area's rich cultural heritage and community spirit.
- Market Days: Visiting local markets on designated days provides an authentic experience of regional produce, crafts, and traditions valued by residents and visitors alike.
Cortona Family Rental Frequently Asked Questions
1. What are the top Family 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 Family Rentals in Cortona:
- Hotel Villa Marsili
- Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
- La Terrazza sulla Valle, with private terrace overlooking the valley!
- Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
- Villa Santa Margherita
- Casale San Martino - Country House Rental in Valdichiana, Tuscany.
- Elegant country barn in Cortona 2bed2bath with shared pool & gorgeous gardens
- Farmhouse in Cortona with pool
- Apartment Me and You Cortona (with romantic outdoor shower on private courtyard)
- Historic 14th Century Church Villa with Private Pool in vineyard near Cortona
2. How many Family Rentals are available in Cortona?
Currently, the total number of properties listed by RBO in 2026 is over 1230 in the Cortona area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Family Rentals in Cortona.
























