Cortona holiday rentals offer the perfect way to immerse yourself in the Tuscan life.
When planning a trip to Tuscany, I knew a hotel wouldn’t give me the experience I wanted. I wanted a place that felt like home—where I could wake up to the sound of church bells, sip my morning tea on a terrace overlooking the hills, and wander to the local market for fresh produce.
Choosing where to stay in Cortona isn’t just about finding a bed for the night; it’s about settling into the town’s charm. Whether you’re looking for a cozy apartment in the historic center or a farmhouse in the countryside, there’s a rental that will make you feel like you truly belong.
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Cortona Holiday Rentals: In-Town Accommodations
Stay right in the heart of Cortona’s Old Town. Perched on a hillside with sweeping views of the Val di Chiana, Cortona is a place where life moves at a different pace. The town is known for its Etruscan history, medieval streets, and beautiful piazzas filled with cafés and wine bars.
It’s the kind of place where you can spend mornings exploring small boutiques, afternoons lingering over a long lunch, and evenings watching the sunset from Piazza della Repubblica.
Staying in town means being steps away from it all—the local markets, the family-run trattorias, and the quiet corners that make Cortona your ultimate Italy getaway.
1. Noah’s Son | 1-bedroom | “Monochrome and modern”
Spread across two floors, the interior is a distinctive mix of period features, such as the flagstone floors and wooden ceiling beams, with a modern monochrome kitchen and grey bathroom.
- 1 bed | 1 bath | Sleeps 2 | 75 sq/m
- Open-concept living, dining and kitchen space
- Home office space in the bedroom
- Good for: solo travellers or couples
2. Sunflower Beams | 2-bedroom | “Old-world charm meets new”
Stay in a historic building spread across two floors with traditional features including exposed dark wood beams and terracotta floor tiles with contemporary-style furnishings. Old-world charm meets new.
- 2 bed | 1 bath | Sleeps 3 | 80 sq/m
- Open-concept living and dining space with a separate kitchen with eating space
- Tiny balcony
- Upper-floor views of city rooftops
- Good for: couples
3. Fresco Fantastico | 3-bedroom | “Grand palazzo”
Sitting on the first floor of a noble palazzo this apartment is full of the opulence of yesteryear. The museum-like details of the home include intricate frescoes and high vaulted ceilings, a black marble fireplace, and large open spaces with lovely views of the townscape and the wider valley.
- 3 bed | 3 bath | Sleeps 6 | 140 sq/m
- Large separate spaces of a foyer, living, dining, and kitchen
- Scenic views of the town and the valley beyond
- Good for: families or couples travelling together
4. View from the Evening | 2-bedroom | “Modern, yet magical”
The terrace is purely magic. A 3-minute walk from the city centre, this stone building sits above one of Cortona’s most beautiful green spaces. The interior is styled with contemporary modern furnishing, yet a relaxed and comfortable feel. To heighten your sense of being relaxed, it even offers an indoor sauna.
- 2 bed | 2 bath | Sleeps 4
- Open-concept living, dining, and kitchen with stellar views
- Outdoor al fresco dining, conversational seating and BBQ
- Scenic views of Cortona’s countryside
- Good for: families or couples/friends
5. The Angelico | 6-bedroom | “Rustic simplicity”
Perched on a hill above Cortona, experience the authentic charm of Italian living with its traditional features, earthy tones and elegant styling. This calming space is perfect for large gatherings.
- 6 bed | 7 bath | Sleeps 12 | 270 sq/m
- Large separate spaces for living, dining, and kitchen
- Pool
- Hilltop view of the town and Cortona’s valley
- Good for: large gatherings of families or friends
6. Il Sogno | 2-bedroom | “Rural romance”
Set amongst Cortana’s rolling green hills, and only a 5-minute walk to the city centre, this renovated 19th-century house is full of original features like exposed beams, brick archways and terracotta tiled floors styled with elegant Italian furnishings like wrought iron bed frames.
- 2 bed | 1 bath | Sleeps 4
- Cozy living and dining space with a separate kitchen open to gardens
- Pool, extensive gardens, outdoor seating and dining under a pergola
- Panoramic scenic views of the countryside
- Good for: couples or small families
Cortona Villa Rentals: Countryside
7. A Sweet Symphony | 2-bedroom | “Historically elegant”
A former church that belonged to an old noble property, is now a restored villa. This elegant home features traditional elements from the once church with modern furnishings and art.
- 2 bed | 2 bath | Sleeps 4
- Located in La Dogana countryside, within walking distance to the village of Pergo and a 10-minute drive to Cortona
- Long open-concept space for living, dining and kitchen with access to the garden
- Scenic countryside views with a pool
- Good for: couples or small families
8. The Juniper Bloom | 2-bedroom | “Rustic modern”
Perched on the hills overlooking the Val di Chiana, this beautiful home seamlessly blends rustic charm with elegant Tuscan style to create a truly unforgettable stay.
- 2 bed | 2 bath | Sleeps 4
- Located in Cortona countryside – a 5-minute drive to Cortona (or 20-minute walk)
- Small open-concept space for living, dining and kitchenette
- Scenic countryside views with a pool
- Good for: couples
9. Vineyard Vistas | 3-bedroom | “Farmhouse Charm”
A farmhouse in the countryside filled with rustic traditional charm and traditional features like its terracotta floors and wooden beam ceilings, but the real show stopper is the outdoor garden, pool and panoramic views.
- 3 bed | 3 bath | Sleeps 6 | 250 sq/m
- Views of Chiana Valley – a 10-minute drive to Cortona
- Cozy spaces for living, dining, and kitchen
- View of gardens and mountains
- Pool, pool house (that can operate as an outdoor kitchen)
- Good for: families
10. The Softest Crimson | 4-bedroom | “Tuscan charmer”
This 19th-century rural farmhouse oozes Tuscan character with its original terracotta-vaulted ceilings, the exposed cork beams and the huge fireplace. Yet, it has modern conveniences like rainfall showers, a trampoline for kids and a ping-pong table in the garden.
- 4 bed | 4 bath | Sleeps 8 | 400 sq/m
- Located in Le Corchie – a 10-minute drive to Cortona
- Large living, dining, and kitchen spaces, plus working space
- View of gardens and pastoral countryside
- Pool, outdoor table tennis, dining al fresco
- Good for: families or friends to stay
11. Ode to Nature | 4-bedroom | “Olive grove vistas”
A former farmhouse turned peaceful retreat with rustic tones and textures, and simple styling of interiors creates a wonderful harmony between tradition and contemporary comforts.
- 4 bed | 4 bath | Sleeps 8 | 190 sq/m
- Located in Cortona countryside – a 5-minute drive to Cortona
- Cozy spaces for living, dining and kitchen
- View of olive groves and pastoral countryside
- Pool and al fresco dining
- Good for: families
12. Timeless in Tuscany | 4-bedroom | “Sinfully soothing”
This gorgeous villa is super stylish with its blend of traditional features and contemporary design – featuring exposed timber beams and a soothing white, grey and blue colour scheme. A fully modern kitchen and free-standing bathtub make this a relaxing stay.
- 4 bed | 4 bath | Sleeps 8 | 189 sq/m
- Located in Cortona countryside – a 5-minute drive to Cortona
- Stylish spaces for living, dining and kitchen
- View of mountains
- Pool and al fresco dining, outdoor lounging spaces
- Good for: families or friends
13. Nature & Beauty | 5-bedroom | “Tuscan tranquility”
An 18th-century dreamy Tuscan retreat within a peaceful garden setting with scenic views of the Chiana Valley. Guests will enjoy the elegant styling of each of its 5 bedrooms with private ensuites and a lift.
- 5 bed | 7 bath | Sleeps 10 | 265 sq/m
- Located in Cortona countryside – a 10-minute drive to Cortona
- Ultra pretty spaces for living, dining and kitchen
- View of gardens and Chiana countryside
- Pool and al fresco dining, outdoor lounging spaces
- Good for: families or friends
Final Thoughts
I hope you found this curated list of the most dreamy places to stay in Cortona Italy helpful. Now, you have the difficult choice of choosing just one.
Once your accommodations in Cortona are secured it’s time for planning your Tuscany itinerary. I will leave you with a few resources to get you started, beyond Cortona, you’ll want to have a car so you can visit other noteworthy Tuscan towns, like:
- Medieval town of Siena
- The ideal Renaissance town of Pienza
- Hidden gem of Arezzo
- The wine lovers’ town of Montepulciano
If you were not successful in finding accommodations in Cortona, check out these places to stay in Montepulciano.
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