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We selected the 912 homes worth renting in this location

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Home spotlights in Castiglione della Pescaia

L'Isola

L'Isola

  • 3 guests

  • 2 bedrooms

Capoliveri, Livorno

On Elba Island, just outside Lacona off the west coast of Italy, this first-floor flat is a hilltop hideaway offering sweeping views of the Tyrrhenian Sea’s turquoise waters. Bright and modern, the open-plan living space is cool and relaxing, with high-beamed ceilings, arty light fixtures, colourful prints and an open-hearth fireplace.

Hillside Vines

Hillside Vines

  • 18 guests

  • 9 bedrooms

Volterra, Pisa

In the undulating Tuscan countryside, this villa sits atop a hill, right on the ancient oil and wine route through olive groves and vineyards. It’s a fifteen-minute drive from Volterra, a medieval walled town with plenty of farm-to-table restaurants and old churches to explore.

Tuscan Pine

Tuscan Pine

  • 14 guests

  • 9 bedrooms

Roccamare, Castiglione della Pescaia

With a private pool, sunny garden, and access to Roccamare's long sandy beach, this villa has outdoor living written all over it. Even with its traditional appearance inside, it feels like a true getaway, especially since it's surrounded by a pine forest.

Maremma Muse

Maremma Muse

  • 10 guests

  • 5 bedrooms

Punta Ala, Castiglione della Pescaia

This beautiful home is nestled amidst a lush pine forest, just a stone's throw from the Punta Ala Equestrian Centre, the Punta Ala Golf Club, and the beaches, so there’s plenty to keep you occupied during your stay. Comfortable for an extended family or large group of friends, this villa invites relaxation.


We selected the top 3% holiday homes in Castiglione della Pescaia Family Friendly Rentals

Explore the 912 most perfect homes in our collection

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Most popular homes in Castiglione della Pescaia

Little Borghis

Little Borghis

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

The Chianti Essence

The Chianti Essence

  • 8 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Sangiovesece Scenery

Sangiovesece Scenery

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Carmella

Carmella

  • 8 guests

  • 4 bedrooms

Scarlino, Tuscany

Two Seas

Two Seas

  • 12 guests

  • 6 bedrooms

Punta Ala, Castiglione della Pescaia

È la Vita

È la Vita

  • 8 guests

  • 4 bedrooms

Ansedonia, Orbetello

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Castiglione della Pescaia, Grosseto, Tuscany, Italy. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Castiglione della Pescaia Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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