Book Luxury Monthly Rentals in Castiglion Fiorentino

We selected the 2920 homes worth renting in this location

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Home spotlights in Castiglion Fiorentino

Upon a Golden Dream

Upon a Golden Dream

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

Whether you're splashing about in the private pool, admiring the Tuscan scenery from the patio or dining on Italian delicacies in the setting sun, this charming villa is the perfect place to call home. Inside, every room oozes traditional character – stone walls here, wooden-clad ceilings there – creating a cosy, comfortable sanctuary.

Garden Oasis Retreat

Garden Oasis Retreat

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

This charming holiday apartment lies in the heart of Cortona, ideal for a romantic getaway. The terrace boasts lovely views of the surrounding landscape, though the outdoor space is overlooked by nearby buildings, so it doesn't feel the most private.

Fresco Fantastico

Fresco Fantastico

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

Sitting on the first floor of a noble palazzo in the typically Tuscan town of Cortona, this apartment will put a smile on the face of anyone fond of the opulence of yesteryear. Wander about the home and you'll spot everything from intricate frescoes and high vaulted ceilings to a black marble fireplace and handsome wooden furnishings.

Casa Castagna

Casa Castagna

  • 6 guests

  • 3 bedrooms

Castiglion Fiorentino, Arezzo

Nothing says ‘la dolce vita’ quite like this authentic Italian villa, which you’ll find tucked away on the outskirts of Castiglion Fiorentino. Nestled deep in the heart of the Tuscan countryside, this rustic home dates back to the 17th century, so it’s no wonder that stepping inside feels like travelling back in time.


We selected the top 3% holiday homes in Castiglion Fiorentino Monthly Rentals

Explore the 2920 most perfect homes in our collection

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Most popular homes in Castiglion Fiorentino

Gramophones & Gazebos

Gramophones & Gazebos

  • 15 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Gardenia Farmhouse

Gardenia Farmhouse

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

Rosewood Manor

Rosewood Manor

  • 18 guests

  • 9 bedrooms

Castiglion Fiorentino, Arezzo

Tuscan Stone & Olive Trees

Tuscan Stone & Olive Trees

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

Ten Green Bottles

Ten Green Bottles

  • 17 guests

  • 6 bedrooms

Foiano della Chiana, Tuscany

Italian Iced Tea

Italian Iced Tea

  • 8 guests

  • 4 bedrooms

Pieve al Toppo, Civitella in Val di Chiana

Sunflower Beams

Sunflower Beams

  • 3 guests

  • 2 bedrooms

Cortona, Arezzo

Tuscan Shadows

Tuscan Shadows

  • 10 guests

  • 5 bedrooms

Castiglion Fiorentino, Arezzo

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Castiglion Fiorentino, Arezzo, Tuscany, Italy, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Castiglion Fiorentino Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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