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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'. (22 results found)

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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

Prices from £706pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Hotel | 1-2 bedrooms | Sleeps 2-4

  • Delightfully small Simpson Hotel
  • Stunning views
  • Two 2-bedroom suites, one cottage

Masseria Le Torri

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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Puglia, Italy

Prices from £761pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Hotel | 1 bedroom | Sleeps 2

  • An elegant Adult Only Simpson Hotel
  • Beautifully restored
  • 9 stylish suites

Tuscany, Italy

Prices from £761pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

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

Tuscany, Italy

Prices from £776pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Apartment | 2 bedrooms | Sleeps 3

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

Tuscany, Italy

Prices from £1,006pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 3 bedrooms | Sleeps 6

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

Tuscany, Italy

Prices from £1,036pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

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

Tuscany, Italy

Prices from £1,411pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 3 bedrooms | Sleeps 6

  • Beautifully restored farm house
  • Stunning panoramic views
  • Heated pool

Puglia, Italy

Prices from £1,436pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 3 bedrooms | Sleeps 6

  • Spacious contemporary villa
  • Panoramic sea view
  • Large lawned garden

Puglia, Italy

Prices from £1,486pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 3 bedrooms | Sleeps 6

  • Beautifully restored trulli
  • Ideal for families or couples
  • Expansive lawned grounds

Puglia, Italy

Prices from £1,636pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 3 bedrooms | Sleeps 6

  • Elegant historic villa
  • Spacious and comfortable
  • Outstanding outdoor area