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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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La Madonnina

Tuscany, Italy

Villa | Bedrooms 1-2 | Sleeps 2-4

  • Two delightful 2-bedroom apartments, one studio cottage
  • Stunning views
  • Beautiful gardens
  • Local bar and grocery shop 10-minute stroll

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

Accommodation Only

  • Apartment

Prices
from

$602pp Total price $1,203
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Casa Momi

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming property for two
  • Comfortable and spacious
  • Stunning views across rolling hills
  • Radda in Chianti 5-minute drive

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

Accommodation Only

  • Villa

Prices
from

$666pp Total price $1,331
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Casa Papa

Tuscany, Italy

Villa | Bedrooms 2 | Sleeps 2-4

  • Charming hillside villa
  • Classic Tuscan views
  • Outdoor kitchen with barbecue and pizza oven
  • 2min drive to Castelfiorentino

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

Accommodation Only

  • Villa

Prices
from

$702pp Total price $1,403
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Casetta Carina

Tuscany, Italy

Apartment | Bedrooms 2 | Sleeps 3

  • Contemporary and comfortable apartment
  • Ideally located to explore Chianti
  • Magnificent large private swimming pool
  • Shops/restaurants/supermarket 10-minute drive

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

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  • Villa

Prices
from

$845pp Total price $1,690
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La Canonica di Cortine Cottages

Tuscany, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Five unique two-bedroom cottages
  • Part of a beautifully restored historic hamlet
  • Informal and friendly
  • Delightful views of Chianti countryside

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

Accommodation Only

  • Cottage

Prices
from

$851pp Total price $1,702
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Trullo Raffaella

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Valle d’Itria location
  • Flexible accommodation
  • Private garden

Prices are based on 2 sharing for 7 nights on Saturday 7 May 2022

Accommodation Only

  • Villa

Prices
from

$892pp Total price $1,784
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Casa al Colle

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elevated, spacious retreat
  • Stunning panoramic views
  • Comfortable interiors
  • Simpson family extras available

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

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  • Villa

Prices
from

$1,018pp Total price $2,036
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La Casa dei Mandorli

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming bijou Chianti villa
  • Stunning views
  • A romantic interlude
  • Beautiful sunset terrace

Prices are based on 2 sharing for 7 nights on Saturday 7 May 2022

Accommodation Only

  • Villa

Prices
from

$1,028pp Total price $2,056
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Simpson Secret – Puglia

Puglia, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Stunning nature reserve location
  • Comfortable country villa
  • Unique natural rock pool
  • Walking distance to beach

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

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  • Villa

Prices
from

$1,084pp Total price $2,168
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Villa Passione

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

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

Prices are based on 2 sharing for 7 nights on Saturday 7 May 2022

Accommodation Only

  • Villa

Prices
from

$1,146pp Total price $2,291
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Travel advice from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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.

Copyright © 2021 Simpson Travel

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  • Destinations

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    France

    France

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

    Mallorca

    Mallorca

    • Pollença & Puerto Pollença

    Greece

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    • Corfu
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    Turkey

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    Italy

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    • Tuscany
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    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
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    Back

  • Holiday inspiration

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    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
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    • 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

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    • Simpson Exclusive
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    Our Blog

    Our Blog

    • Where to go
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    • Family travel
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    • Give the gift of travel
  • About us

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    • Why Simpson Travel?
    • Travel arrangements
    • Advance Registration
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      Last updated on 20/01/2022 at 08:35 PM

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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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