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Luxury couples holidays in Italy

The landscapes, art and architecture of Italy are timelessly captivating and for couples on holiday there are few places as romantic as a medieval Tuscan village or Renaissance city for a lingering candlelit dinner. And our accommodation, be it luxury villa or boutique hotel, was chosen as the perfect complement.

As specialists in villa holidays for two, we spent months on the road cherry-picking the very best locations for your Italian holiday. Tuscany offers stunning scenery – including the wine-growing area of Chianti – plus a choice of villas for couples within driving distance of many fascinating hilltop towns and villages.

Alternatively, couples can find a villa for two amidst the hills and valleys of Umbria, Lazio to the south or Liguria in the north west, where you’ll also be within easy reach of the Italian Riviera. But wherever you go, Simpson Travel caters for couples who want to indulge a taste for the finer things in life.

Discover Italy’s famous cities

While much of Tuscany has art galleries and museums to admire, Florence is the birthplace of the Renaissance and staying in one of our Tuscany villas means you’ll be close enough to visit. A living, breathing art gallery both inside and out, the countless churches and grand squares rub shoulders with designer stores and upmarket restaurants to accommodate devotion in all its forms.

And then there’s Venice – one of the world’s most iconic backdrops for a couples’ holiday. Few places are quite so atmospheric and although all our villas for two promise a wonderful time away, this famous city is guaranteed to send hearts a-fluttering.

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Showing search results for 'Italy'. (21 results found)

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Tuscany, Italy

Accom only prices from £1,300 Help

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Villa | 3 bedrooms | Sleeps 6

  • Stylish and comfortable barn conversion
  • Extensive garden with small lake
  • Cooking classes available

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Tuscany, Italy

Accom only prices from £650 Help

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Apartment | 2 bedrooms | Sleeps 4

  • Beautiful converted apartment
  • 17th-century building
  • Private terrace with delightful views

La Madonnina

United by warm welcomes, excellent service and attention to detail, our handpicked Simpson Hotels include our unique Adult Only Collection and, for families, comfortable, versatile accommodation in locations well suited to guests of all ages.
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Tuscany, Italy

Accom only prices from £660 Help

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Hotel | 1-2 bedrooms | Sleeps 2-4

  • Delightfully small Simpson hotel
  • Stunning views
  • Beautiful gardens

Tuscany, Italy

Accom only prices from £750 Help

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Villa | 1 bedroom | Sleeps 2

  • Charming property for two
  • Comfortable and spacious
  • Stunning views across rolling hills

Tuscany, Italy

Accom only prices from £800 Help

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Apartment | 2 bedrooms | Sleeps 3

  • Contemporary and comfortable apartment
  • Ideally located to explore Chianti
  • Magnificent swimming pool

Tuscany, Italy

Accom only prices from £1,110 Help

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Villa | 1 bedroom | Sleeps 2

  • Charming bijou Chianti villa
  • 'Room with a view'
  • A romantic interlude

Liguria, Italy

Accom only prices from £1,700 Help

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Villa | 2 bedrooms | Sleeps 4

  • Charming hillside villa
  • On Ligurian coast
  • Delightful sea view

Umbria, Italy

Accom only prices from £2,200 Help

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Villa | 5 bedrooms | Sleeps 9

  • Wonderful country villa
  • Elegant and comfortable
  • Lovely summer kitchen with outstanding view

Venice, Italy

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Apartment | 3 bedrooms | Sleeps 6

  • Magnificent Venetian building
  • Balcony with canal view
  • Elegant and spacious

Tuscany, Italy

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Hotel | 1 bedroom | Sleeps 2

  • Part of a beautifully restored historic hamlet
  • Informal and friendly
  • Delightful views of Chianti countryside