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Siena Five Bedroom Homes

We selected the 1110 homes worth renting in this location

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Home spotlights in Siena

Being of Beauty

Being of Beauty

  • 18 guests

  • 9 bedrooms

Lilliano, Castellina in Chianti

Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories.

Classic Moments

Classic Moments

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills.

The Soul Of Wine

The Soul Of Wine

  • 14 guests

  • 7 bedrooms

Gaiole in Chianti, Siena

To say this luxury handcrafted stone villa took our breath away, well, that's an understatement. This place is enchanting with its vistas over a patchwork of Chianti Classico vineyards, olive groves, and oak forests.

Siena on My Mind

Siena on My Mind

  • 12 guests

  • 6 bedrooms

Sovicille, Tuscany

Families will love this stone villa. Featuring a main house, a studio apartment, and a separate cottage, you'll have plenty of space to chill out together or enjoy some quiet time alone.

We selected the top 3% holiday homes in Siena Five Bedroom Homes

Explore the 1110 most perfect homes in our collection

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Most popular homes in Siena

A Glass of Brunello

A Glass of Brunello

  • 10 guests

  • 5 bedrooms

San Miniato, Pisa

The Vine Vineyard

The Vine Vineyard

  • 18 guests

  • 11 bedrooms

Castelnuovo Berardenga, Siena

The Olive House

The Olive House

  • 10 guests

  • 5 bedrooms

Murlo, Siena

Verdant Valley

Verdant Valley

  • 15 guests

  • 8 bedrooms

Poggibonsi, Siena

Citrus Pavillion

Citrus Pavillion

  • 20 guests

  • 9 bedrooms

Gaiole in Chianti, Siena

Land of Beauty

Land of Beauty

  • 12 guests

  • 6 bedrooms

Castelnuovo Berardenga, Siena

The Sweetest Life

The Sweetest Life

  • 32 guests

  • 16 bedrooms

Monteriggioni, Siena

Siena Ceremony

Siena Ceremony

  • 8 guests

  • 5 bedrooms

Castelnuovo Berardenga, Siena

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Frequently asked questions

Spacious 5 bedroom homes in Siena, Tuscany, Italy. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best 5 bedroom homes that Siena, Tuscany, Italy has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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