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  • Destinations

    Destinations

    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

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    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
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    Villas

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    Teen-friendly villas
    Beachfront villas
    Villas with heated pools
    Villas near the beach
    Villas near a restaurant
    Family villas
  • Hotels

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    • Couples holidays
    • Beach holidays
    • Large group holidays
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    • 10 night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking holidays in Crete
    • Special Interest Holidays

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

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Luxury villa holidays in Italy

Italy may be a place we’ve seen before, in photographs, paintings, at the cinema: those ancient villages and rolling hills are timeless and unforgettable – but to experience it, first hand, from the comfort of your own luxury villa is to really appreciate what la dolce vita is really all about.

Couples and families return to this irresistible destination year after year – the good food, excellent wines and centuries of art and culture converging to create a backdrop for the sweetest of experiences and the most inspiring of luxury villa holidays.

Which luxury villa will suit you best?

From Tuscany to Umbria and Lazio, from a 10th-century fortress to sprawling estates or romantic hideaways for two, there’s a villa that is your perfect fit – a luxury villa with a private pool that gives you privacy plus a location that puts you within easy reach of some of Italy’s best attractions. Whether you want to be near the masterpieces of Florence and surrounded by the vineyards of Chianti or near Liguria’s Italian Riviera, our villas offer our guests a chance to experience the true magic of Italy.  

Be our guest

We chose our luxury villas not only for their superb locations but also for the quality of care and attention our guests receive when they stay there. Villa owners and experienced property managers welcome you with open arms, often bringing vegetables from the garden and home-cooked goodies to treat you. And if you want to know the best restaurant, the loveliest walks or the most welcoming child-friendly attractions, they’re the ones to talk to. Or they’ll just leave you to enjoy your luxury villa holiday, undisturbed and with a myriad of pleasurable pursuits to fill your days.

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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 12 October 2024

Accommodation Only

  • Apartment

Prices
from

£488pp Total price £976
View details
Go to property page

Casa Momi

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Comfortable and spacious
  • Stunning views across rolling hills
  • Walking distance to restaurant
  • Radda in Chianti 5-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 12 October 2024

Accommodation Only

  • Villa

Prices
from

£498pp Total price £996
View details
Go to property page

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 5 October 2024

Accommodation Only

  • Villa

Prices
from

£520pp Total price £1,040
View details
Go to property page

Casa Rosanna

Puglia, Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic hideaway
  • Beautiful sea views
  • Private and stylish
  • Charming Valle d'Itria location

Prices are based on 2 sharing for 7 nights on Saturday 4 May 2024

Accommodation Only

  • Villa

Prices
from

£580pp Total price £1,160
View details
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La Lamia

Puglia, Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic hideaway
  • Wonderful countryside views
  • Peaceful setting in Valle d'Itria
  • Cisternino 5min drive

Prices are based on 2 sharing for 7 nights on Saturday 5 October 2024

Accommodation Only

  • Villa

Prices
from

£605pp Total price £1,210
View details
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Casetta Carina

Tuscany, Italy

Apartment | Bedrooms 2 | Sleeps 3

  • Contemporary and comfortable apartment
  • Heart of Chianti location
  • Magnificent large private swimming pool
  • Shops/restaurants/supermarket 10-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 12 October 2024

Accommodation Only

  • Villa

Prices
from

£655pp Total price £1,310
View details
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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 4 May 2024

Accommodation Only

  • Villa

Prices
from

£678pp Total price £1,355
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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 4 May 2024

Accommodation Only

  • Villa

Prices
from

£760pp Total price £1,520
View details
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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 2 sharing for 7 nights on Saturday 4 May 2024

Accommodation Only

  • Villa

Prices
from

£780pp Total price £1,560
View details
Simpson Secrets

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
Simpson Secrets

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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 12 October 2024

Accommodation Only

  • Villa

Prices
from

£811pp Total price £1,621
View details
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Why travel with us..?

Talk to one of our experts

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A brand you can trust

A brand you can trust

See what others say about us

See what others say about us
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
  • Runner up Telegraph travel awards 2023

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Holiday ideas

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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.

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