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Italy Holidays 2022

If you’re looking for a slice of la dolce vita in 2022 our ltalian portfolio is the place to start. From romantic cottages in the Tuscan hills to luxury family villas near Puglia’s sensational coastline, Italy is a destination that never disappoints. Book with confidence where 2022 prices are available, or use our Advance Registration scheme to secure your preferred dates with a fully refundable deposit.

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Villa Donatella

Umbria, Italy

Villa | Bedrooms 5 | Sleeps 6-9

  • Calming and welcoming country house
  • Spacious and comfortable
  • Captivating views
  • Excellent location to explore Umbria

Prices are based on 2 sharing for 7 nights on Saturday 24 September 2022

Accommodation Only

  • Villa

Prices
from

$1,374pp Total price $2,747
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Villa Aurora

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stylish and contemporary villa
  • Delightful countryside views
  • Shaded balcony for al fresco dining
  • Bar/restaurant 15-minute walk

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
from

$1,395pp Total price $2,789
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Trulli Gianpaolo

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Val d’Itria location
  • Picturesque garden
  • Private pool

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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$1,398pp Total price $2,795
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Le Guardie

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming renovated villa
  • Stylish interiors
  • 20min walk to central Florence
  • Flexible stays available

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

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$1,463pp Total price $2,925
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Villa Mille Desideri

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 11

  • Beautifully positioned villa
  • Breathtaking views
  • Comfortable and welcoming
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
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$1,610pp Total price $3,219
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Colto dei Pallanti

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Beautifully restored farm house
  • Stunning panoramic views
  • Heated pool
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
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$1,613pp Total price $3,226
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Villa Aia

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stylish contemporary villa
  • Beautiful countryside views
  • Peaceful and secluded
  • Media room

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

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$1,681pp Total price $3,362
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La Perla del Mare

Puglia, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Two-bedroom suite
  • Stunning sea views
  • Direct access to the sea
  • Private garden and terrace

Prices are based on 2 sharing for 7 nights on Saturday 1 October 2022

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  • Suite

Prices
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$1,957pp Total price $3,913
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Villa Favorita

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 8

  • Elegant historic villa
  • Spacious and comfortable
  • Heated swimming pool
  • Exceptional outdoor area

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,976pp Total price $3,952
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Trulli Rosalinda

Puglia, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Beautifully restored trulli
  • Ideal for families and multi-generational groups
  • Expansive lawned grounds
  • Peaceful setting amongst the olive groves

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,976pp Total price $3,952
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Travel advice

For up-to-date advice and information on travel from the UK, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500. For travel from countries outside the UK, please visit your corresponding government website.

The air holidays and flights shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is ATOL 5858. ATOL protection extends primarily to customers who book and pay in the United Kingdom. Find out more about ATOL. Simpson Travel is the trading name of Far & Wide Ltd.

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  • Destinations

    Destinations

    France

    France

    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Sivota
    • Zakynthos

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
  • Villas

    Villas

    • Villas with childcare
    • Luxury villas
    • Off the beaten track villas
    • Car-free villas
    • Large group villas
    • Villas together
    • Romantic villas for two
    • Family Favourite villas
    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
    • Villas near a restaurant

    Back

  • Hotels

    Hotels

    • Simpson Hotels
    • Partner hotels
    • Family hotels
    • Beachfront hotels
    • Adult-only hotels
    • Romantic hotels for two
    • Hotels with childcare
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    Back

  • Holiday inspiration

    Holiday inspiration

    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
    • Large group holidays
    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
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    Collections

    Collections

    • Simpson Exclusive
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    Our Blog

    Our Blog

    • Where to go
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    • What's new
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    • Give the gift of travel
  • About us

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    • Why Simpson Travel?
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You'll also be able to enter into our new quarterly competition, with the chance to win a holiday

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Sign up to receive our latest news and exclusive offers, direct to you inbox

You'll also be able to enter into our new quarterly competition, with the chance to win a holiday

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