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Luxury villas, boutique Simpson Hotels and unforgettable holidays

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Luxury couples holidays in Italy

The landscapes, art and architecture of Italy are timelessly captivating and for couples on holiday there are few places as romantic as a medieval Tuscan village or Renaissance city for a lingering candlelit dinner. And our accommodation, be it luxury villa or boutique hotel, was chosen as the perfect complement.

As specialists in villa holidays for two, we spent months on the road cherry-picking the very best locations for your Italian holiday. Tuscany offers stunning scenery – including the wine-growing area of Chianti – plus a choice of villas for couples within driving distance of many fascinating hilltop towns and villages.

Alternatively, couples can find a villa for two amidst the hills and valleys of Umbria, Lazio to the south or Liguria in the north west, where you’ll also be within easy reach of the Italian Riviera. But wherever you go, Simpson Travel caters for couples who want to indulge a taste for the finer things in life.

Discover Italy’s famous cities

While much of Tuscany has art galleries and museums to admire, Florence is the birthplace of the Renaissance and staying in one of our Tuscany villas means you’ll be close enough to visit. A living, breathing art gallery both inside and out, the countless churches and grand squares rub shoulders with designer stores and upmarket restaurants to accommodate devotion in all its forms.

And then there’s Venice – one of the world’s most iconic backdrops for a couples’ holiday. Few places are quite so atmospheric and although all our villas for two promise a wonderful time away, this famous city is guaranteed to send hearts a-fluttering.

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La Lamia

Puglia, Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic hideaway
  • Wonderful countryside views
  • Peaceful setting in Valle d'Itria
  • Cisternino 5min drive

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

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  • Villa

Prices
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$513pp Total price $1,025
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Reserve now for 2024 with a fully refundable deposit of $625

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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

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  • Villa

Prices
from

$617pp Total price $1,233
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Reserve now for 2024 with a fully refundable deposit of $625

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Casa Rosanna

Puglia, Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic hideaway
  • Beautiful sea views
  • Private and stylish
  • Charming Valle d'Itria location

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

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  • Villa

Prices
from

$625pp Total price $1,250
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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

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  • Villa

Prices
from

$644pp Total price $1,288
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Reserve now for 2024 with a fully refundable deposit of $625

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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 14 October 2023

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  • Villa

Prices
from

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

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Masseria Francescani

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2-3

  • Elegant Masseria in Southern Puglia
  • Beautifully renovated and elegantly appointed
  • Delightful garden and pool terrace
  • Exclusive restaurant

Prices are based on 2 sharing for 7 nights on Saturday 13 May 2023

Accommodation Only

  • Suite & breakfast

Prices
from

$854pp Total price $1,707
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Reserve now for 2024 with a fully refundable deposit of $625

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Masseria Mongiò dell Elefante

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 1-4

  • Stylishly restored Masseria in southern Puglia
  • Elegant restaurant and bar
  • Complimentary welcome dinner
  • Beautiful gardens and grounds

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

Accommodation Only

  • Suite & breakfast

Prices
from

$942pp Total price $1,883
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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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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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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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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 6 May 2023

Accommodation Only

  • Villa

Prices
from

$1,094pp Total price $2,188
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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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Masseria Le Torri

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2

  • Elegant Partner Hotel
  • 9 stylish suites
  • One complimentary dinner for stays of 3 nights or more
  • Polignano and beach 15-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 24 June 2023

Accommodation Only

  • Suite & breakfast

Prices
from

$1,119pp Total price $2,237
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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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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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  • 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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  • ATOL Number 5858
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  • 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
    • Kaş

    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

    Back

  • Hotels

    Hotels

    • Simpson Hotels
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    • Beachfront hotels
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    Back

  • 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
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    • Simply Simpson
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    Our Blog

    Our Blog

    • Where to go
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    • What's new
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    • Family travel
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    • Give the gift of travel
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