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Rural retreats in Italy

For the ultimate ‘get away from it all’ countryside holiday, Italy’s abundance of unspoilt landscapes and picturesque villages offer the discerning traveller a taste of times gone – and an irresistible choice of rural retreats. Allow Simpson Travel to be your guide to the rolling hills and valleys of Tuscany and Umbria.

Of course, Italy’s fertile interior has more than scenery to savour: you’ll find freshly-grown local produce in the country markets across Tuscany, as well as numerous seasonal festivals celebrating everything from Chianti’s fine wines to steaks and chestnuts. It’s a taste of authentic Italy that you can take back to your cosy rural retreat for a meal bursting with traditional flavours

Umbria, sometimes known as ‘the green heart of Italy‘, offers similar delights. Not only is the countryside a feast for the eyes, it rewards you more literally with traditional delicacies such as truffles and cured meats, as well as its own collection of world-famous wines.

And after a day of exploration, your Simpson Travel luxury villa will be waiting for you: the perfect countryside retreat. Hand-picked for the quality of its finish and furnishings, and its tranquillity, your rural hideaway gives you the space to relax and re-charge, close enough to shops and restaurants to make life easy, secluded enough to give you the gift of perfect peace and privacy.

Then you’ll be ready to emerge again, all set for another adventure in the beautiful Italian countryside.

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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

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  • Villa

Prices
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$980pp Total price $1,959
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Reserve now for 2024 with a fully refundable deposit of $625

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Villa Donatella

Umbria, Italy

Villa | Bedrooms 5 | Sleeps 6-9

  • Calming and welcoming country house
  • Spacious and comfortable
  • Captivating views
  • Excellent location to explore Umbria

Prices are based on 2 sharing for 7 nights on Saturday 20 May 2023

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Prices
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$1,344pp Total price $2,688
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Reserve now for 2024 with a fully refundable deposit of $625

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Tenuta Fonte

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Elegantly understated
  • Huge grounds
  • Very private
  • Close to Ostuni

Prices are based on 2 sharing for 7 nights on Saturday 6 May 2023

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  • Villa

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$1,344pp Total price $2,688
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Reserve now for 2024 with a fully refundable deposit of $625

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Trulli Gianpaolo

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Val d’Itria location
  • Picturesque garden
  • Private pool

Prices are based on 2 sharing for 7 nights on Saturday 6 May 2023

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  • Villa

Prices
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$1,407pp Total price $2,813
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Reserve now for 2024 with a fully refundable deposit of $625

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Villa Mille Desideri

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 11

  • Beautifully positioned villa
  • Breathtaking views
  • Comfortable and welcoming
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 6 May 2023

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  • Villa

Prices
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$1,469pp Total price $2,938
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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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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

  • Understated luxury
  • Huge grounds
  • Beaches 5min drive
  • Lecce 5km

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

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$1,507pp Total price $3,013
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Colto dei Pallanti

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Beautifully restored farm house
  • Stunning panoramic views
  • Heated pool
  • Spa area with sauna and Jacuzzi

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

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  • Villa

Prices
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$1,585pp Total price $3,169
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Reserve now for 2024 with a fully refundable deposit of $625

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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 7 October 2023

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  • Villa

Prices
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$1,657pp Total price $3,313
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Reserve now for 2024 with a fully refundable deposit of $625

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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 14 October 2023

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  • Villa

Prices
from

$2,157pp Total price $4,313
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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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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.
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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 14 October 2023

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  • Villa

Prices
from

$3,625pp Total price $7,250
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Reserve now for 2024 with a fully refundable deposit of $625

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See what others say about us

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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
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  • 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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    • Fornalutx & Sóller
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    • Calvi & The Balagne
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  • Villas

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    • Villas with childcare
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    • Off the beaten track villas
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    • 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
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    Back

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