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  • Villas and apartments (27)
  • Hotels (4)
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27 search results found

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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
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 16 October 2021

Accommodation Only

  • Apartment

Prices
from

$541pp Total price $1,081
View details
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Casa Brilli

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable refurbished villa
  • Set in an extensive manicured garden
  • Ideal for two families travelling together
  • Delightful outdoor pergola

Prices are based on 2 sharing for 7 nights on Saturday 16 October 2021

Accommodation Only

  • Villa

Prices
from

$579pp Total price $1,157
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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 16 October 2021

Accommodation Only

  • Villa

Prices
from

$580pp Total price $1,160
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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 1 May 2021

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  • Villa

Prices
from

$668pp Total price $1,335
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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 16 October 2021

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  • Villa

Prices
from

$773pp Total price $1,545
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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

Prices are based on 2 sharing for 7 nights on Saturday 5 June 2021

Accommodation Only

  • Cottage

Prices
from

$823pp Total price $1,646
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Trullo Raffaella

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Val d’Itria location
  • Flexible accommodation
  • Private garden

Prices are based on 2 sharing for 7 nights on Saturday 9 October 2021

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  • Villa

Prices
from

$930pp Total price $1,860
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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 1 May 2021

Accommodation Only

  • Villa

Prices
from

$930pp Total price $1,860
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Simpson Secrets

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
Simpson Secrets

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Simpson Secret – Puglia

Puglia, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Stunning nature reserve location
  • Comfortable country villa
  • Unique natural rock pool
  • Walking distance to beach

Prices are based on 2 sharing for 7 nights on Saturday 9 October 2021

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  • Villa

Prices
from

$962pp Total price $1,923
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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 9 October 2021

Accommodation Only

  • Villa

Prices
from

$985pp Total price $1,969
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Simpson Travel in the press

  • ‘[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

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For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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

    Destinations

    France

    France

    • Côte d'Azur
    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Sivota
    • Zakynthos

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Central Corsica
    • Porto Vecchio & Bonifacio
    • The Valinco
    • West Coast
  • 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

  • Hotels

    Hotels

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

    Back

  • Holiday types

    Holiday types

    • 2021 Holidays
    • Couples holidays
    • Easter holidays
    • Half-term holidays
    • Holidays with childcare
    • Multi-gen holidays
    • Large group holidays
    • Solo Travel
    • Beach holidays
    • Twin centre holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Experiences and Activities

    Back

  • Collections

    Collections

    • Simpson Exclusive
    • Simpson Secrets
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    • Simply Simpson
    • Simpson Kids

    Back

  • About us

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