Love & Romance
12 guests
6 bedrooms
Gambassi Terme, Florence
We can't think of many things more idyllic than sitting by the pool with a glass of Tuscan wine, overlooking the rolling vineyards. But you're in luck, as that's what awaits you at this stunning slice of paradise.
Tuscan Breeze
2 guests
1 bedrooms
San Gimignano, Siena
Nestled in the Tuscan countryside, surrounded by vineyards and olive trees, this apartment promises a true escape from it all. Ideal as a couple’s bolthole, while there’s no oven here and the traditional interiors may not be everyone’s cup of tea, the outdoor space is sure to be a hit with all.
A Flickering Candle
10 guests
5 bedrooms
Volterra, Pisa
Set amid beautiful green countryside just outside the pretty medieval town of Volterra, this striking stone home – which was originally constructed to serve as a watchtower – is brimming with quintessential Tuscan charm and a host of handy amenities, making it the perfect base from which to set out and explore the highlights of the local area. Spend days unwinding within the tranquil environs of the home and its sprawling gardens filled with mature trees and boasting a lovely fenced swimming pool area.
Ancient Hills
6 guests
3 bedrooms
San Gimignano, Siena
Just a short drive from historic San Gimignano and its iconic towers, this apartment is a delightful base for six. It’s on a complex in a stunning position close to vineyards and olive groves, and the views of the surrounding hills are breathtaking.
Explore the 2026 most perfect homes in our collection
You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in San Gimignano, Siena, Tuscany, Italy. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury San Gimignano Home to Rent with a Swimming Pool today, and set up a holiday to remember.
