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  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Pollensa & Puerto Pollensa
    • Palma

    Greece

    Greece

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    • Crete
    • Ithaca
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    • Lefkada
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    • Paxos
    • Zakynthos
    • Sivota & Epirus
    • The Peloponnese

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    • Bozburun Peninsula
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    • Kalkan
    • Kaş

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Luxury villa holidays in Tuscany | Simpson Travel

Luxury villa holidays in Tuscany

Tuscany is the inspiration behind countless films, paintings and novels and its timeless landscapes continue to enchant our guests. Whether you choose a home-from-home in the heart of Chianti, a rural retreat near Arezzo or a sleepy farmhouse overlooking the gently rolling hills of the Valle D'Orcia, our luxury Tuscany escapes allow you to experience the real joy of la dolce vita.

Couples and families return to this irresistible region year after year – the good food, excellent wines and centuries of art and culture converging to create a backdrop for the sweetest of experiences, where life is beautiful and our award-winning villas never fail to delight.

Which luxury escape 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 escape 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 properties not only for their superb locations but also for the quality of care and attention our guests receive when they stay there. All our 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 Tuscan villa holiday, undisturbed and with a myriad of pleasurable pursuits to fill your days.

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Villa Da Vinci

Tuscany , Italy

Villa | Bedrooms 6 | Sleeps 13

  • 16m private pool
  • Breath-taking panoramic views
  • Stunning guest cottage
  • Set in the heart of Chianti

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

Accommodation Only
Villa
Prices
from
$5,663pp
Total price $11,325
View details
Reserve now for 2026 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $650, fully refundable when prices are published

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Simpson Signature

Discover our top-rated, most luxurious villas, with exceptional service to match.
Simpson Signature

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Villa Petraia

Tuscany , Italy

Villa | Bedrooms 5 | Sleeps 10

  • Simpson Signature villa
  • Classic Tuscan views
  • Elegant décor
  • Heated swimming pool

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

Accommodation Only
Villa
Prices
from
$7,657pp
Total price $15,314
View details
Reserve now for 2026 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $650, fully refundable when prices are published

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Villa Bellosguardo

Tuscany , Italy

Villa | Bedrooms 3 | Sleeps 8

  • Superb views over Florence
  • Exceptionally rare holiday rental
  • Air-conditioned
  • Roof-top lounge, hot tub & summer kitchen

Prices are per person, based on 2 sharing for 7 nights
on Saturday 5 July 2025

Accommodation Only
Villa
Prices
from
$10,082pp
Total price $20,163
View details
Reserve now for 2026 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $650, fully refundable when prices are published

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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-perfect villa 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

  • ‘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

  • Our stay was also infused with his thoughtful brand of hospitality, matched with that of the experienced tour operator (Simpson Travel). Author: Claire Irvin, The Times

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
  • Award - Conde Naste Traveller 2024

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Holiday ideas

  • Holidays in Corsica
  • Villas in Corsica
  • Holidays in France
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  • Holidays in Italy
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  • 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 © 2025 Simpson Travel

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