Book Luxury Vacation Rentals for May in Tuscany

We selected the 1248 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Tuscany

Artistic Grapes

Artistic Grapes

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls.

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Head into the Tuscan hills just outside the charming village of Cellai and keep an eye out for an imposing villa with its own bell tower. Almost unbelievably, this stunning property will be your home from home for however long you decide to stay.

Rooftop Views

Rooftop Views

  • 2 guests

  • 1 bedrooms

Walled City, Lucca

Boasting stunning views of the town's historic rooftops and medieval towers, this two-level apartment is the ideal Lucca retreat. It’s light and airy with lots of character features, but we should probably mention that the bathroom is a bit dated.

A Glass Of Chianti

A Glass Of Chianti

  • 2 guests

  • 1 bedrooms

Montespertoli, Florence

This apartment shares its location with a family-run farm in pretty Montespertoli. The family produces wine and olive oil from a picturesque spot amid the gentle Chianti hills, surrounded by vineyards, olive groves and woods – it’s delightfully rustic.


We selected the top 3% holiday homes in Tuscany Vacation Rentals for May

Explore the 1248 most perfect homes in our collection

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Most popular homes in Tuscany

Sing, Prima Donna

Sing, Prima Donna

  • 6 guests

  • 3 bedrooms

Castelfranco Piandiscò, Arezzo

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Tuscan Rose

Tuscan Rose

  • 10 guests

  • 3 bedrooms

Terranuova Bracciolini, Arezzo

The Royal Estate

The Royal Estate

  • 12 guests

  • 6 bedrooms

Lucca, Tuscany

The Maestro Puccini

The Maestro Puccini

  • 8 guests

  • 4 bedrooms

Massarosa, Lucca

Oliva Farmhouse

Oliva Farmhouse

  • 4 guests

  • 2 bedrooms

Montespertoli, Florence

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Check upcoming rates & availability for Tuscany Vacation Rentals for May


Frequently asked questions

Discover our exclusive collection of the finest Vacation Rentals for May that Tuscany, Italy has to offer, and mark the month with an unforgettable trip. At Plum Guide, we carefully select only the very best homes around, so you know that every rental is one to be proud of. Each home in our range comes fully furnished, with a well-equipped kitchen, all linen, and essential toiletries included. Our meticulous testing process ensures that no stone is left unturned, with everything from shower pressure and Wifi speed to a home's design aesthetic being thoroughly tested. Book a luxury Holiday Rental for May in Tuscany today, and see what all the fuss is about. If you need any guidance, call on our experts, ready night and day to help you find your ideal home.

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