13 Dreamy Places to Stay in Cortona Italy

This is what dreams are made of when you look at these dreamy places to stay in Cortona Italy. Cortona is an idyllic hilltop town made famous in Frances Mayes’s book Under the Tuscan Sun and the movie that followed.

There’s something for everyone among these 13 villas for rent in Cortona Italy. They all conjure up their own dream version of Tuscany. Most of these villas in Cortona offer sublime views, al fresco dining and pools.

I spent almost a week in Tuscany, very close to Cortona. So I can absolutely recommend that Cortona makes the ideal place to stay in Tuscany. Not only is the town beautiful, but it also makes a great home base to explore other nearby places.

I hope you enjoy this curated list of the best hotels and vacation rentals in Cortona – sorry, no Cortona Airbnb or B&B here – these are far superior choices.

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Places to Stay in Cortona Italy

1. Noah’s Son | 1-bedroom | “Monochrome and modern”

Stay Cortona Noah 1

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.

Cortona Italy Accommodation Details:

  • 1 bed | 1 bath – Sleeps 2 | 75 sq/m
  • In town apartment
  • 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”

white sofa, fireplace with dark beamed ceiling in a vacation rentals in cortona italy

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.

Cortona Accommodation Details:

  • 2 bed | 1 bath – Sleeps 3 | 80 sq/m
  • In town apartment
  • 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. Il Sogno | 2-bedroom | “Rural romance”

brick stone villas for rental in cortona italy with steps shutters on window and trees

Set amongst Cortana’s rolling green hills, 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.

Accommodation in Cortona Details:

  • 2 bed | 1 bath – Sleeps 4
  • Villa for rent within walking distance of Cortona (5 minutes)
  • 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

4. Fresco Fantastico | 3-bedroom | “Grand palazzo”

mint green painted fresco walls with sofa, chair, lamp and windows in a villa cortona

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.

Cortona Tuscany Accommodation Details:

  • 3 bed | 3 bath – Sleeps 6 | 140 sq/m
  • In town apartment
  • Large separate spaces – foyer, living, dining, kitchen
  • Scenic views of the town and the valley beyond
  • Good for: families

5. Vista Valle | 3-bedroom | “Farmhouse vistas”

al fresco dining at villa in cortona tuscany

A stone farmhouse set in the rolling hills features exposed beam ceilings, a tiled kitchen and a relaxed comfortable interior. The bedrooms are simple, yet traditional with an ivy fresco in one, a four-poster bed in the second room, and a canopied pair of beds in the third.

Cortona Vacation Rentals details:

  • 3 bed | 2 bath – Sleeps 6 | 100 sq/m
  • In town villa
  • Open-concept living, dining, tiny kitchenette
  • Outdoor al fresco dining, pool
  • Scenic views of Cortona’s countryside
  • Good for: families or couples/friends

6. The Angelico | 6-bedroom | “Rustic simplicity”

stone floor, beamed ceiling, table and chairs for dining in one the the vacation rentals in cortona italy

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.

Cortona Holiday Rentals Details:

  • 6 bed | 7 bath – Sleeps 12 | 270 sq/m
  • In town villa
  • 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

Villas for Rent in Cortona Italy (with a short drive)

7. A Sweet Symphony | 2-bedroom | “Historically elegant”

white building with beige stone trim with trees as one of the places to stay in cortona italy

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.

Villa Cortona details:

  • 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
  • Parking available
  • Good for: couples or small families

8. The Juniper Bloom | 2-bedroom | “Rustic modern”

brown leather sofa, beamed ceiling, exposed brick in accommodations in cortona

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.

Villa Cortona details:

  • 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
  • Parking available
  • Good for: couples

9. Regina | 3-bedroom | “Old-world treasures”

dining table with view to tuscan countryside from holiday rentals in cortona

A house in the countryside dating back to 1700, filled with antique furniture and traditional features like its terracotta ceilings and wooden beams, the gilded gold frames and an open hearth.

Villa Cortona details:

  • 3 bed | 3 bath – Sleeps 6 | 190 sq/m
  • Located in Campaccio – a 5-minute drive to Cortona
  • Cozy spaces for living, dining, and kitchen
  • View of gardens and mountains
  • Parking available
  • Good for: families

10. The Softest Crimson | 4-bedroom | “Tuscan charmer”

pool, loung chairs, garden with stone villa for rent in cortona italy accommodations

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.

Villa Cortona Accommodation Details:

  • 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”

dining table staircase with terra cotta brick floor in vacation rentals in cortona

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.

Villa Cortona Accommodation Details:

  • 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. Another Life | 4-bedroom | “Sinfully soothing”

gray sofa, stone fireplace with beamed ceiling and artwork in cortona italy accommodations

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.

Villa Cortona details:

  • 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”

white sofa and chairs with fireplace in Cortona holiday rentals

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.

Villa Cortona details:

  • 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

Plum Guide’s Vacation Rentals Cortona Italy

Perhaps you’ve not heard of Plum Guide, the vacation rental property that undergoes a rigorous vetting process for every holiday home appearing on their website. They represent only 3% of all vacation rental properties- across low, medium and high price points.

Plum Guide is known as the Michelin star of holiday homes.

Using 150 criteria that go into what makes for a perfect stay. This drastically contrasts with the well-known and popular Airbnb- which has hidden costs and in some cases a poor reputation.

I’ve personally stayed at Plum Guide properties several times. They are my go-to favourite and can’t recommend them enough! Each stay has exceeded my expectations. I’ve also recommended them to clients as part of my custom trip planning services and often hear comments of “It was one of our favourite aspects of our trip“. If you value high-quality property rentals, look no further than Plum Guide.

Hotels near Cortona

Now if you are more interested in staying in a hotel in Cortona Italy these properties are bound to be of interest. This curated list of 7 in-town or hotels near Cortona will be perfect for any vacation to Tuscany.

Best Hotels in Cortona Italy

  1. Hotel San Luca – a 4-star property located on Cortona’s Piazza Garibaldi, a scenic square and viewpoint, offers classic-style rooms with balconies and terraces to admire the view.
  2. Monastero di Cortona Hotel & Spa – a 5-star property located in an ancient monastery with a pool and gardens, and breakfast is included in this hotel in Cortona.
  3. Hotel Villa Marsili – an 18th-century hotel in Cortona near the historic centre. This 4-star property includes breakfast and has pretty gardens for guests to enjoy.

Best Hotels near Cortona

  1. Villa di Piazzano – an elegant historic resort with landscaped gardens, a pool and al fresco dining for guests. This 5-star property is part of the Small Luxury Hotels of the World group and has an onsite restaurant and fitness centre. Only a 5-minute drive to town.
  2. Villa Aurea – an 18th-century villa with a wellness centre, spa, pool and on-site restaurant called La Corte which includes breakfast. Only a 5-minute drive to Cortona.
  3. Relais La Corte dei Papi – one of the most luxurious accommodations in Cortona from the restaurant to the gardens and pool to the attractive rooms. Located in a tranquil setting with uninterrupted views and only a 10-minute drive to Cortona.
  4. Relais & Chateau II Falconiere – a 17th-century manor that features a Michelin-starred restaurant, wellness centre, and pool. This 5-star property has views of the hotel’s vineyards and is only a short 5-minute drive to Cortona.

As a Holidaymaker

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. What will it be…that perfect hotel or a vacation rental in Cortona?

Once your accommodations in Cortona are secured it’s time for planning your itinerary. I will leave you with a few resources to get you started.

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