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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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Villa Montelopio

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elegant villa in hilltop village
  • Stunning panoramic views
  • Elegant and spacious interiors
  • Castiglioncello beach 52km/1hr drive

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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$2,113pp Total price $4,225
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Rosa

Tuscany, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Historic 19th century building
  • Extensive private grounds
  • 16-metre swimming pool
  • Tower lounge with beautiful views

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$2,210pp Total price $4,420
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Villa Vita

Umbria, Italy

Villa | Bedrooms 3 | Sleeps 2-6

  • Stunning contemporary villa
  • State-of-the-art design
  • Heated swimming pool and sauna
  • Exceptional countryside views

Prices are based on 2 sharing for 7 nights on Saturday 24 September 2022

Accommodation Only

  • Villa

Prices
from

$2,340pp Total price $4,680
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Da Vinci

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 12

  • Exceptional manor house
  • Spacious and comfortable
  • Set in the heart of Chianti
  • Outstanding views

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$2,968pp Total price $5,935
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Privata

Tuscany, Italy

Villa | Bedrooms 8 | Sleeps 15

  • Quiet and peaceful country retreat
  • Flexible accommodation for families or group of friends
  • Spectacular views
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$4,076pp Total price $8,151
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Reserve now for 2023 with a fully refundable deposit of $650

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Simpson Exclusive

When only the best will do...


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Villa Petraia

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Simpson Exclusive
  • Classic Tuscan views
  • Elegant décor
  • Swimming pool

Prices are based on 2 sharing for 7 nights on Saturday 1 October 2022

Accommodation Only

  • Villa

Prices
from

$5,142pp Total price $10,283
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Reserve now for 2023 with a fully refundable deposit of $650

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Simpson Exclusive

When only the best will do...


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La Tenuta

Puglia, Italy

Villa | Bedrooms 9 | Sleeps 18

  • Simpson Exclusive
  • Stylish villa set in 5 hectares
  • Superb 13-metre pool
  • Versatile layout

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

Accommodation Only

  • Villa

Prices
from

$6,312pp Total price $12,623
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Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Villa Castrum

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Magnificent 5-bedroom villa
  • Part of a beautifully restored historic hamlet
  • In the heart of Chianti
  • Spacious and comfortable
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Villa Romantica

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 12

  • Beautiful stone farmhouse
  • Spacious and comfortable
  • Daily maid service
  • Yoga and Pilates studio
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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La Canonica di Cortine Cottages

Tuscany, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Five unique two-bedroom cottages
  • Part of a beautifully restored historic hamlet
  • Informal and friendly
  • Delightful views of Chianti countryside
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, 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

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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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  • Destinations

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