Book Luxury Monthly Rentals in Castiglion Fiorentino

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Home spotlights

The Whispering Hills

The Whispering Hills

  • 6 guests

  • 2 bedrooms

Arezzo, Tuscany

Giving way to sweeping views of the Arezzo hills, this villa's outdoor space is undoubtedly the main draw. With a swimming pool and ample seating for everything from alfresco dining to sunbathing, it's made for sun worshippers.

Pistachio Pesto

Pistachio Pesto

  • 8 guests

  • 2 bedrooms

Arezzo, Tuscany

This home is a true haven nestled right in the heart of Arezzo. With its luscious garden and rustic interior, it's the perfect place to kick back and relax away from the hustle and bustle.

Timeless Harmony

Timeless Harmony

  • 14 guests

  • 5 bedrooms

Arezzo, Tuscany

Made up of a main building and two annexes, nestled on a promontory and enjoying stunning views of the city and surrounding countryside, this home is a gorgeous blend of the traditional and the super modern. Sit by the fireplace in the main building or admire the art adorning the walls, or out by the private pool and catch some sun on the poolside loungers under the trees.

Arezzo Stone

Arezzo Stone

  • 15 guests

  • 7 bedrooms

Arezzo, Tuscany

This stone villa is perfectly harmonious with its surroundings – situated high in the Arezzo hills, this renovated house sits amongst organic orchards and centuries-old beech, strawberry and juniper trees. You’ll experience unrivalled privacy in this impressive estate, which focuses on connecting you with your natural surroundings.


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

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Most popular homes

The Vineyard House

The Vineyard House

  • 16 guests

  • 13 bedrooms

Arezzo, Tuscany

Vita Toscana

Vita Toscana

  • 12 guests

  • 6 bedrooms

Arezzo, Tuscany

The Healer of Tubbiano

The Healer of Tubbiano

  • 8 guests

  • 4 bedrooms

Arezzo, Tuscany

Dreams of Yesterday

Dreams of Yesterday

  • 10 guests

  • 5 bedrooms

Santa Firmina, Arezzo

Pastel Caramel

Pastel Caramel

  • 11 guests

  • 5 bedrooms

Arezzo, Tuscany

A Benigni Classic

A Benigni Classic

  • 2 guests

  • 1 bedrooms

Quartiere di Porta Crucifera, 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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