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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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Casa Brilli

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable refurbished villa
  • Set in an extensive manicured garden
  • Ideal for two families travelling together
  • Delightful outdoor pergola

Prices are based on 4 sharing for 7 nights on Saturday 16 October 2021

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  • Villa

Prices
from

$289pp Total price $1,157
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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 4 sharing for 7 nights on Saturday 1 May 2021

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from

$334pp Total price $1,335
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Trullo Raffaella

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

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

Prices are based on 4 sharing for 7 nights on Saturday 9 October 2021

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  • Villa

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$465pp Total price $1,860
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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 4 sharing for 7 nights on Saturday 9 October 2021

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from

$492pp Total price $1,969
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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 4 sharing for 7 nights on Saturday 16 October 2021

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  • Villa

Prices
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$501pp Total price $2,003
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Simpson Kids

Whether you're travelling with babes in arms, toddlers or school-age children, our Simpson Kids programme will help you find the perfect holiday to suit your family. From hotels with expert childcare to villas with complimentary infant packs and garden games for the kids, we have everything you need for a stress-free family holiday.
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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 4 sharing for 7 nights on Saturday 1 May 2021

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  • Villa

Prices
from

$511pp Total price $2,042
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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 4 sharing for 7 nights on Saturday 9 October 2021

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  • Villa

Prices
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$537pp Total price $2,146
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Villa Rudy

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Spacious family villa
  • Generous entertaining space
  • Outdoor kitchen
  • Private heated swimming pool

Prices are based on 4 sharing for 7 nights on Saturday 1 May 2021

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  • Villa

Prices
from

$783pp Total price $3,133
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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 4 sharing for 7 nights on Saturday 16 October 2021

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  • Villa

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$864pp Total price $3,455
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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 4 sharing for 7 nights on Saturday 5 June 2021

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  • Cottage

Prices
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$412pp Total price $1,646
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Simpson Travel in the press

  • ‘[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

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Holiday ideas

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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.

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  • Destinations

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    France

    France

    • Côte d'Azur
    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
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    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
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    Turkey

    Turkey

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    • Bozburun Peninsula
    • Islamlar & Uzumlu
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    Italy

    Italy

    • Tuscany
    • Umbria
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    Corsica

    Corsica

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  • 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
    • Car-free hotels

    Back

  • Holiday types

    Holiday types

    • 2021 Holidays
    • Couples holidays
    • Easter holidays
    • Half-term holidays
    • Holidays with childcare
    • Multi-gen holidays
    • Large group holidays
    • Solo Travel
    • Beach holidays
    • Twin centre holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Experiences and Activities

    Back

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