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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 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 14 October 2023

Accommodation Only

  • Villa

Prices
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$594pp Total price $1,188
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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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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 14 October 2023

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  • Apartment

Prices
from

$604pp Total price $1,208
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Reserve now for 2024 with a fully refundable deposit of $625

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Casa Momi

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming property for two
  • Comfortable and spacious
  • Stunning views across rolling hills
  • Radda in Chianti 5-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 14 October 2023

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  • Villa

Prices
from

$617pp Total price $1,233
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Reserve now for 2024 with a fully refundable deposit of $625

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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 2 sharing for 7 nights on Saturday 14 October 2023

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  • Villa

Prices
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$644pp Total price $1,288
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Reserve now for 2024 with a fully refundable deposit of $625

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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 based on 2 sharing for 7 nights on Saturday 14 October 2023

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  • Villa

Prices
from

$657pp Total price $1,313
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Reserve now for 2024 with a fully refundable deposit of $625

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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 14 October 2023

Accommodation Only

  • Villa

Prices
from

$813pp Total price $1,625
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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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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 6 May 2023

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  • Villa

Prices
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$841pp Total price $1,682
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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 2 sharing for 7 nights on Saturday 7 October 2023

Accommodation Only

  • Villa

Prices
from

$980pp Total price $1,959
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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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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 14 October 2023

Accommodation Only

  • Villa

Prices
from

$990pp Total price $1,979
View details
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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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.
Simpson Kids

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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 2 sharing for 7 nights on Saturday 6 May 2023

Accommodation Only

  • Villa

Prices
from

$1,052pp Total price $2,103
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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
  • Villas in France
  • Holidays in Greece
  • 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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    • Provence
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    • Calvi & The Balagne
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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

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