3 Affordable and Dog-Friendly Luxury Tuscan Villas to Rent

What could be more fabulous then renting a whole villa in the Tuscan hillside, whether for a few days or a few weeks? Especially if it’s large enough to hold a whole family or a whole crew of friends, ready for summer days spent by the pool and evenings feasting on good Italian wine and delicious food by a fireplace!

While there are plenty of super-expensive options available for rent, I’ve instead dug three affordable options. All come with a swimming pool and are highly recommenced, with plenty of 5-star reviews, but are available for €220 per night or less, while sleeping up to 8 guests. And they’re perfect whether or not you’re travelling with a dog in tow, as they’re all dog-friendly.

Travelling with a dog? Check out my tips for travelling in Italy with a dog

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Villa in the Tuscan countryside

Orione Apartment Near San Gimignano (Avg. €212/night for 6)

Osservatorio Villa is a large, gorgeous villa surrounded by manicured lawns about a 15 minute drive west of San Gimignano. Sleeping up to 11 people, it also handily offers the option to just rent half the villa, the Orione Apartment, sleeping up to 6 people.

There’s easy access to the property along a paved and lit road, however, most guests choose to spend their time relaxing on the property. The outdoor covered loggia is the ideal spot to spend the days and evenings, overlooking the large pool and gardens.

Hosts Neva and Giovanni live in the adjacent house, but leave guests alone to give you complete privacy, except to make sure you are settled and be available for anything that comes up.

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One of the charming villages of the Orcia Valley

Colourful Villa Sabrina Near San Gimignano (Avg. €167/night for 7)

This charming villa near San Gimignano has been delightfully decorated in true Tuscan style. From the yellow tinged walls of the exterior to the blue washed kitchen cupboards, you’ll immediately feel ready to enjoy a Tuscan holiday.

Naturally there is a private swimming pool to offer you respite from the summer heat, complete with sun loungers and additional lounge chairs under a sun umbrella. All is surrounded by a beautifully manicured garden, perfect for when dining or just enjoying a glass of wine outdoors. Inside are three bedrooms, including a spacious master suite with four-poster bed, big enough for seven occupants.

San Gimignano is just 5km away, perfect for visiting in the evening when day trippers are gone, plus Siena and Florence are both within 50km drive. Plus your host Sabrina lives just next door, offering her fine hospitality and treats to guests.

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Olive groves in Tuscany

Podere Benedettino with Infinity Pool Near Florence (Avg. €199/night for 8)

The stand-out feature of this villa is the amazing infinity pool perched on the hillside to the east of Florence. It’s the perfect place to relax day or night while staying in this restored farmhouse, although there’s also a large, fully-covered entertaining area for lounging or dining, and a wonderful fire-pit area for chilly evenings.

Inside the interiors have been charmingly decorated, a mixture of soft hues and rustic touches. There’s three bedrooms and two bathrooms, big enough for eight guests. There’s a minimum stay of three nights, with all the linen including pool towels and bathrobes changed weekly for longer stays.

During the days, head into Florence to explore its many art galleries and historical sites. Or use the provided trekking map to go hiking in the nearby hills, or go mountain bike riding from the property’s entrance.

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Florence by night

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Affordable Luxury Tuscan Villas

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