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  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Pollensa & Puerto Pollensa

    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
  • Hotels

    Hotels

    Simpson Hotels
    Partner hotels
    Family hotels
    Beachfront hotels
    Adult-only hotels
    Romantic hotels for two
    Hotels with childcare
    Car-free hotels
  • Holiday inspiration

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    Holiday Types

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

    Family holidays

    Family holidays

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

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    • Simpson Exclusive
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    • Simpson Kids
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    More inspiration

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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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Casa Papa

Tuscany , Italy

Villa | Bedrooms 2 | Sleeps 2-4

  • Our most popular Tuscan property
  • Charming hillside villa
  • Classic Tuscan views
  • Outdoor kitchen with barbecue and pizza oven

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£520pp
Total price £1,040
View details
Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
Simply Simpson

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Casa Momi

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

  • 12m private swimming pool
  • Stunning views across rolling hills
  • Walking distance to restaurant
  • Radda in Chianti 5-minute drive

Prices are per person, based on 2 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only
Villa
Prices
from
£530pp
Total price £1,060
View details
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Casa Rosanna

Puglia , Italy

Villa | Bedroom 1 | Sleeps 2

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

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£595pp
Total price £1,190
View details
Go to property page

Casa al Colle

Tuscany , Italy

Villa | Bedrooms 5 | Sleeps 10

  • Spectacular hillside location
  • Fantastic cook available
  • Ideal for a group/two families
  • Pizza oven

Prices are per person, based on 2 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only
Villa
Prices
from
£815pp
Total price £1,630
View details
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Villa Ddò

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 6

  • Striking contemporary villa
  • Tranquil rural setting overlooking vineyards
  • Walking distance to facilities of neighbouring Relais
  • Easy access to Cisternino and Valle d'Itria

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£855pp
Total price £1,710
View details
Go to property page

Tenuta Fonte

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

  • Ideal configuration for 2 families
  • 3 hours of housekeeping included 6 days pw
  • Huge grounds
  • Very private

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,145pp
Total price £2,290
View details
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Trullo Ashi

Puglia , Italy

Villa | Bedrooms 5 | Sleeps 9

  • Beautiful high-spec villa
  • Spacious gardens with charming views
  • Large heated swimming pool
  • Outdoor kitchen with pizza oven

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,145pp
Total price £2,290
View details
Go to property page

Villa Mille Desideri

Tuscany , Italy

Villa | Bedrooms 6 | Sleeps 11

  • Peaceful and secluded
  • Ideal for 2 families
  • 14m private swimming pool
  • Table tennis, table football, boules, football goals

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,180pp
Total price £2,360
View details
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Colto dei Pallanti

Tuscany , Italy

Villa | Bedrooms 3 | Sleeps 6

  • In the heart of Chianti
  • Stunning panoramic views
  • Heated, gated 12m private pool
  • Spa area with sauna and Jacuzzi

Prices are per person, based on 2 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only
Villa
Prices
from
£1,273pp
Total price £2,545
View details
Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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Masseria Specchia

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stunning Simpson Exclusive
  • Understated luxury
  • Huge grounds
  • Set in beautiful Salento

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,395pp
Total price £2,790
View details
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Why travel with us..?

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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

  • 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

  • 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.

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