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Luxury villa holidays in Skopelos

Thanks to the magic of Hollywood (and Mamma Mia!), Skopelos has become many people’s idea of the classic Greek Island and the perfect backdrop for a family holiday or romantic escape. Happily, the reality doesn’t disappoint and Skopelos remains charmingly unspoilt, albeit with a generous sprinkling of luxury villas and private pools in its green and peaceful landscape.

Accommodation, Skopelos-style

Despite its starring film role, we are happy to report that Skopelos is still remarkably quiet and undeveloped. The island capital has been designated a Traditional Settlement of Outstanding Beauty, and holiday villas on Skopelos tend to be tasteful conversions rather than brash new builds. There’s no compromise on comfort however, as all our villas have a private pool, WiFi and air-conditioned bedrooms as a minimum. The island is wonderfully romantic, so we’ve taken care to include plenty of villas for two, as well as family-sized accommodation.

Make the most of your villa holiday

If you’re thrilled by the idea of exploring deserted coves by boat, following a winding goat track through shady pine forest to a spectacular view point or doing some pool-side bird spotting in your private villa garden, then a Skopelos holiday is for you. Simpson Travel’s villas are located in the south of Skopelos, and most are within 5-10 minutes’ drive of Skopelos town and Glysteri or Stafilos beaches, where you’ll find sunbeds to rent and tavernas in high season.

Find out more about holidays in Skopelos

For advice on where to stay, our specialist travel consultants have visited every one of our luxury villas and you can also find out more about the island in our guide to Skopelos.

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Showing search results for 'Greece, Skopelos'. (8 results found)

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Skopelos, Greece

Prices from £1,220pp 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 and peaceful cottage
  • Delightful hideaway
  • Sea and country views

Simpson Secret – Skopelos

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
Simpson Secrets

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Skopelos, Greece

Prices from £1,245pp Help

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

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Villa | 2 bedrooms | Sleeps 4

  • Stunning views
  • Complete privacy
  • Wonderfully romantic

Skopelos, Greece

Prices from £1,307pp 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

  • Beautifully positioned cottage
  • Stunning views
  • Peaceful hideaway

Skopelos, Greece

Prices from £1,307pp Help

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

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Villa | 2 bedrooms | Sleeps 4

  • Stunningly positioned house
  • Beautiful sea and mountain views
  • Comfortable and welcoming

Skopelos, Greece

Prices from £1,320pp 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

  • Beautiful enclosed gardens
  • Large private pool
  • Family friendly

Skopelos, Greece

Prices from £1,329pp Help

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

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Villa | 2 bedrooms | Sleeps 4

  • Delightfully positioned house
  • Beautiful mature gardens
  • Sea views over the Aegean

Skopelos, Greece

Prices from £1,334pp Help

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

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Villa | 2 bedrooms | Sleeps 4

  • Delightfully private villa
  • Beautiful landscaped gardens
  • Spacious and comfortable

Skopelos, Greece

Prices from £1,358pp 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

  • Romantic hideaway
  • Beautiful sea and mountain views
  • Charming and comfortable