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Luxury villas, boutique Simpson Hotels and unforgettable holidays

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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 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 7 October 2023

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  • Villa

Prices
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$322pp Total price $1,288
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Reserve now for 2024 with a fully refundable deposit of $625

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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 4 sharing for 7 nights on Saturday 14 October 2023

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  • Apartment

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$359pp Total price $1,434
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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 4 sharing for 7 nights on Saturday 6 May 2023

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  • Villa

Prices
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$421pp Total price $1,682
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Villa Flavia

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 6

  • Spacious contemporary villa
  • Panoramic sea view
  • Large lawned garden
  • Polignano a Mare beach 10-minute drive

Prices are based on 4 sharing for 7 nights on Saturday 6 May 2023

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  • Villa

Prices
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$485pp Total price $1,938
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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 7 October 2023

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  • Villa

Prices
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$490pp Total price $1,959
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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 6 May 2023

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  • Villa

Prices
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$526pp Total price $2,103
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Tenuta Fonte

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Elegantly understated
  • Huge grounds
  • Very private
  • Close to Ostuni

Prices are based on 4 sharing for 7 nights on Saturday 6 May 2023

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  • Villa

Prices
from

$563pp Total price $2,250
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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 6 May 2023

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  • Villa

Prices
from

$641pp Total price $2,563
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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 14 October 2023

Accommodation Only

  • Villa

Prices
from

$672pp Total price $2,688
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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 4 sharing for 7 nights on Saturday 30 September 2023

Accommodation Only

  • Villa

Prices
from

$672pp Total price $2,688
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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

  •  Silver British travel awards 2017
  • Award - Telegraph 2018
  • Award - Baby 2019
  • Award - Conde Naste Traveller 2020
  • Award - Conde Naste Traveller 2021
  • Award - Conde Naste Traveller 2022
  •  Silver British travel awards 2021/22

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Holiday ideas

  • Holidays in Corsica
  • Villas in Corsica
  • Holidays in France
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  • Villas in Greece
  • Holidays in Italy
  • Villas in Italy
  • Holidays in Mallorca
  • Villas in Mallorca
  • Holidays in Turkey
  • Villas in Turkey

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
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

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

    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
    • Family villas

    Back

  • Hotels

    Hotels

    • Simpson Hotels
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    Back

  • Holiday inspiration

    Holiday inspiration

    Holiday Types

    Holiday Types

    • Couples holidays
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    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking Holidays in Crete
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays

    Collections

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    • Simpson Exclusive
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    Our Blog

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