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We selected the 3668 homes worth renting in this location

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Home spotlights in Poggibonsi

Chianti Sunset

Chianti Sunset

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Nestled in the Chianti countryside between Siena and Florence, this home has serenity running through its core. Sat atop a hill, surrounded by olive groves and vineyards (the site is actually an active organic winery), it’s impossible not to relax here.

Vine & Blossom

Vine & Blossom

  • 8 guests

  • 4 bedrooms

Barberino Tavarnelle, Florence

Vineyards stretch as far as the eye can see at this Chianti villa. Settings rarely get more picturesque than this – we can already picture lazy afternoons by the private pool and alfresco drinks on the covered terrace, all while admiring the views.

One of the Greats

One of the Greats

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests. As you walk about the house for the first time, you might find it difficult to single out a favourite room.

Beyond the Bridge

Beyond the Bridge

  • 7 guests

  • 3 bedrooms

Colle di Val d'Elsa, Siena

This charming apartment is in the old town of Colle di Val d'Elsa, a typically medieval region of Tuscany famous for crystal glass production. It’s a ten-minute stroll into the centre where you’ll find restaurants, cafés and archaeological museums beyond the ancient town walls.


We selected the top 3% holiday homes in Poggibonsi Family Friendly Rentals

Explore the 3668 most perfect homes in our collection

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Most popular homes in Poggibonsi

A Truffled Retreat

A Truffled Retreat

  • 19 guests

  • 10 bedrooms

Castellina in Chianti, Siena

Cypress Reflections

Cypress Reflections

  • 14 guests

  • 7 bedrooms

Barberino Tavarnelle, Florence

First Of The Summer Wine

First Of The Summer Wine

  • 6 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Sun of Splendour

Sun of Splendour

  • 15 guests

  • 7 bedrooms

Fonterutoli, Castellina in Chianti

Cypress Drive

Cypress Drive

  • 3 guests

  • 1 bedrooms

Colle di Val d'Elsa, Siena

Medieval Lullabies

Medieval Lullabies

  • 8 guests

  • 3 bedrooms

Torri, Poggibonsi

Pulpa de Tomate

Pulpa de Tomate

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Italian Serenity

Italian Serenity

  • 24 guests

  • 12 bedrooms

Poggibonsi, Siena

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Poggibonsi, Siena, 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 Poggibonsi 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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