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Villas

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Holiday inspiration

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Holiday Types

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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

Accommodation Only

  • Apartment

Prices
from

$604pp Total price $1,208
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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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

Accommodation Only

  • Villa

Prices
from

$617pp Total price $1,233
View details
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 7 October 2023

Accommodation Only

  • Villa

Prices
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$644pp Total price $1,288
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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

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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
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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 30 September 2023

Accommodation Only

  • Villa

Prices
from

$1,086pp Total price $2,172
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Reserve now for 2024 with a fully refundable deposit of $625

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Le Guardie

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming renovated villa
  • Stylish interiors
  • 20min walk to central Florence
  • Flexible stays available

Prices are based on 2 sharing for 7 nights on Saturday 30 September 2023

Accommodation Only

  • Villa

Prices
from

$1,157pp Total price $2,313
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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 7 October 2023

Accommodation Only

  • Villa

Prices
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$1,548pp Total price $3,095
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Reserve now for 2024 with a fully refundable deposit of $625

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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

Accommodation Only

  • Villa

Prices
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$1,585pp Total price $3,169
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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 14 October 2023

Accommodation Only

  • Villa

Prices
from

$2,032pp Total price $4,063
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Reserve now for 2024 with a fully refundable deposit of $625

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Why travel with us

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CONTACT US

A brand you can trust

A brand you can trust

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-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
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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 © 2022 Simpson Travel

Menu

  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

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

    Turkey

    Turkey

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

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
  • 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
    Family villas
  • Hotels

    Hotels

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

    Holiday inspiration

    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
    • Large group holidays
    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking Holidays in Crete
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays

    Collections

    Collections

    • Simpson Exclusive
    • Simpson Secrets
    • Simpson Hotels
    • Simply Simpson
    • Simpson Kids
    • Simpson Bespoke

    Our Blog

    Our Blog

    • Where to go
    • What to do
    • What's new
    • Views and reviews
    • Family travel
    • 2023 holidays
    • Give the gift of travel
  • About us

    About us

    Why Simpson Travel?
    Travel arrangements
    Advance Registration
    Our heritage
    Awards
    Reviews
    Loyalty Club
    Our Destination Specialists
    Giving back
    Our blog
    Our digital brochure
    Our Partners
    Responsible Tourism
  • Contact us

    Contact us

    Sign up to emails
    Gift Vouchers
    Press & PR
    Property owners
    Simpson Travel App
    FAQs
  • Late availability

    Late availability

  • My Account
  • Wishlist
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