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Luxury holiday apartments in Italy

When it came to choosing our luxury holiday apartments, we faced an exciting challenge. In a country that has so much to offer: breathtaking scenery, centuries of history, some of the finest art in the world and world-famous food and wine, how do you find the accommodation to live up to it?

The luxury holiday apartments we chose reflect traditional Italian style whilst giving you a comfortable, well-located place to stay, which means access to the many pleasures that this beautiful country has to offer from the vineyards of Chianti to the waterways and winding streets of Venice.

Making the most of your Italian holiday

The local culinary traditions and wineries are world renowned, and for those who like to get out and about, an apartment holiday in Italy also offers cycling and walking trails, galleries and museums, glorious parks and natural hot springs for the indulgence of pure relaxation. And of course the awe-inspiring cathedrals of Siena, San Gimignano and Florence, the artisan workshops and the timeless towns and villages are the stuff that memories are made of.

Be our guest

We chose our luxury apartments not only for their enviable locations but also for their owners and managers who welcome our guests with open arms. And if you want to know where’s best for wine, the ideal lunch stops on a day out or where to find the best souvenirs, they’re the ones to talk to. Or they’ll just leave you to enjoy your luxury apartment holiday in peace, with a hundred pleasurable ways to fill your days.

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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 16 October 2021

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  • Villa

Prices
from

$773pp Total price $1,545
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Il Sogno

Puglia, Italy

Apartment | Bedroom 1 | Sleeps 2

  • Unique apartment in historic centre of Ostuni
  • Traditional building, stylishly appointed
  • Heated plunge-pool with hydromassage
  • Quiet and convenient location

Prices are based on 2 sharing for 7 nights on Saturday 15 May 2021

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  • Apartment

Prices
from

$1,252pp Total price $2,504
View details

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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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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

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • 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
    • Central Corsica
    • Porto Vecchio & Bonifacio
    • The Valinco
    • West Coast
  • 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

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  • 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

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    Collections

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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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