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Luxury family holidays in Italy

Italy is a destination that welcomes guests of all ages with a warm embrace of wholesome food and wine, sun-kissed landscapes and a host of interesting places to explore. And at the end of the day, there’s always the chance to gather round the dining table to enjoy that precious time together.

For little ones who want room to run around, the sprawling Italian countryside never runs out of space for exploring, horseriding or cycling and our villas, with their extensive, lovingly tended gardens, private pools and stone terraces, only enhance the pleasures of the great outdoors.

Even history lessons take place outside here, with the historic spires, domes and towers of Florence, Siena, Pisa and San Gimignano, the narrow winding streets of medieval hilltop villages or the mirror-like waterways of Venice – and when it comes to dining, parents can relax in the knowledge that children will be warmly welcomed, whatever their age. From upmarket fine dining to pizza and a hundred different flavours of ice cream, there’s food in abundance for everyone, as well as some of the best wines in the world.

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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 4 sharing for 7 nights on Saturday 24 September 2022

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  • Villa

Prices
from

$959pp Total price $3,835
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Reserve now for 2023 with a fully refundable deposit of $650

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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 4 sharing for 7 nights on Saturday 8 October 2022

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  • Suite

Prices
from

$978pp Total price $3,913
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Reserve now for 2023 with a fully refundable deposit of $650

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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 4 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$988pp 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 4 sharing for 7 nights on Saturday 15 October 2022

Accommodation Only

  • Villa

Prices
from

$988pp Total price $3,952
View details
Reserve now for 2023 with a fully refundable deposit of $650

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Masseria Borgo San Benedetto

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Imposing 18th century masseria
  • Spacious elegant interiors
  • Walled garden with pool
  • 5-minute drive to Conversano

Prices are based on 4 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,024pp Total price $4,095
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Montelopio

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elegant villa in hilltop village
  • Stunning panoramic views
  • Elegant and spacious interiors
  • Castiglioncello beach 52km/1hr drive

Prices are based on 4 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
from

$1,056pp Total price $4,225
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Rosa

Tuscany, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Historic 19th century building
  • Extensive private grounds
  • 16-metre swimming pool
  • Tower lounge with beautiful views

Prices are based on 4 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,105pp Total price $4,420
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Villa Vita

Umbria, Italy

Villa | Bedrooms 3 | Sleeps 2-6

  • Stunning contemporary villa
  • State-of-the-art design
  • Heated swimming pool and sauna
  • Exceptional countryside views

Prices are based on 4 sharing for 7 nights on Saturday 24 September 2022

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  • Villa

Prices
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$1,170pp Total price $4,680
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Da Vinci

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 12

  • Exceptional manor house
  • Spacious and comfortable
  • Set in the heart of Chianti
  • Outstanding views

Prices are based on 4 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$1,484pp Total price $5,935
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Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Villa Privata

Tuscany, Italy

Villa | Bedrooms 8 | Sleeps 15

  • Quiet and peaceful country retreat
  • Flexible accommodation for families or group of friends
  • Spectacular views
  • Simpson family extras available

Prices are based on 4 sharing for 7 nights on Saturday 15 October 2022

Accommodation Only

  • Villa

Prices
from

$2,038pp Total price $8,151
View details
Reserve now for 2023 with a fully refundable deposit of $650

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Reviews

Simpson Travel in the media

  • ‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph

  • ‘So how did we find the near-perfection that was Villa Cabanellas in Mallorca? The first step was to approach… Simpson Travel… we needed expertise, not just blinding choice.’ Author: Sunday Times Travel Magazine, The Villas Handbook

  • ‘The Simpson Travel check-in at Heathrow’s Terminal 5 was seamless.’ Author: Family Traveller, Katy Hill

  • ‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden

  • ‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden

Awards

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Holiday ideas

  • Holidays in Corsica
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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.

Copyright © 2022 Simpson Travel

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  • Destinations

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    France

    France

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

    Mallorca

    Mallorca

    • Fornalutx & Sóller
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    Italy

    Italy

    • Tuscany
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    Corsica

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    • Calvi & The Balagne
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    • The Valinco
  • Villas

    Villas

    • Villas with childcare
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    • 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

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    • Couples holidays
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