San Gimignano Guest Houses

We selected the 3436 homes worth renting in this location

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Home spotlights in San Gimignano

Heart of Tuscany

Heart of Tuscany

  • 2 guests

  • 1 bedrooms

San Gimignano, Siena

Flooded with light, courtesy of the arched windows, this home is perfect for a couple’s getaway. Traditional in style, the main thing missing here is an oven – but isn’t that the perfect excuse to dine out on fine Italian cuisine instead?

Tempo Giusto

Tempo Giusto

  • 6 guests

  • 3 bedrooms

San Gimignano, Siena

Slow the pace at this rural hayloft converted villa, nestled in the beauty of the Chianti hills. Whether it’s the picturesque views, alluring turquoise pool, lush cypress-lined garden, or the gently shaded canopy area, this home encourages outdoor living – you’ll have no choice but to surrender yourself to the serenity of the Tuscan countryside.

A Tuscan Adventure

A Tuscan Adventure

  • 4 guests

  • 2 bedrooms

Gambassi Terme, Florence

You’ll find this villa nestled on a resort alongside two other homes, surrounded by landscaped gardens that are perfect for making the most of the Tuscan sun. Granted, its traditional interiors may not be everyone’s cup of tea, but the location makes it easy to explore some of the area's most iconic towns.

Envelope For A Love Letter

Envelope For A Love Letter

  • 6 guests

  • 3 bedrooms

Gambassi Terme, Florence

The small Tuscan village of Gambassi was once a famous spa destination, where the highest of Florentine nobility came for their rest and recuperation. You may not share a last name with 13th-century popes, but we think you’ll find blissful peace here all the same.


We selected the top 3% holiday homes in San Gimignano Guest Houses

Explore the 3436 most perfect homes in our collection

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Most popular homes in San Gimignano

Into the Olive Grove

Into the Olive Grove

  • 10 guests

  • 5 bedrooms

San Filippo a Ponzano, Barberino Tavarnelle

The Noble Hour

The Noble Hour

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Beyond the Bridge

Beyond the Bridge

  • 7 guests

  • 3 bedrooms

Colle di Val d'Elsa, Siena

A Tuscan Soul

A Tuscan Soul

  • 4 guests

  • 3 bedrooms

San Gimignano, Siena

Chestnut & Stone

Chestnut & Stone

  • 16 guests

  • 5 bedrooms

Gambassi Terme, Florence

Lavender & Sunshine

Lavender & Sunshine

  • 10 guests

  • 5 bedrooms

Fiano, Certaldo

Campi di Lavanda

Campi di Lavanda

  • 12 guests

  • 6 bedrooms

Barberino Tavarnelle, Florence

Groves & Vines

Groves & Vines

  • 8 guests

  • 4 bedrooms

Gambassi Terme, Florence

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Frequently asked questions

Looking for guesthouse style accommodation in San Gimignano, Siena, Tuscany, Italy? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that San Gimignano, 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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