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  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Pollensa & Puerto Pollensa

    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
  • 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 Greece
    • Special Interest Holidays

    Family holidays

    Family holidays

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

    Collections

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

    More inspiration

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    • Our Blog
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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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Casa Papa

Tuscany , Italy

Villa | Bedrooms 2 | Sleeps 2-4

  • Our most popular Tuscan property
  • Charming hillside villa
  • Classic Tuscan views
  • Outdoor kitchen with barbecue and pizza oven

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£520pp
Total price £1,040
View details
Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
Simply Simpson

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Casa Momi

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

  • 12m private swimming pool
  • Stunning views across rolling hills
  • Walking distance to restaurant
  • Radda in Chianti 5-minute drive

Prices are per person, based on 2 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only
Villa
Prices
from
£530pp
Total price £1,060
View details
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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 per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£595pp
Total price £1,190
View details
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Villa Ddò

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 6

  • Striking contemporary villa
  • Tranquil rural setting overlooking vineyards
  • Walking distance to facilities of neighbouring Relais
  • Easy access to Cisternino and Valle d'Itria

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£855pp
Total price £1,710
View details
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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
  • Cook service available

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£488pp
Total price £976
View details
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Casetta Carina

Tuscany , Italy

Apartment | Bedrooms 2 | Sleeps 3

  • Ideal for couples
  • Heart of Chianti location
  • Magnificent 18m private swimming pool
  • Terrace with sublime views

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Apartment
Prices
from
£656pp
Total price £1,312
View details
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 per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£811pp
Total price £1,621
View details
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Le Guardie

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming renovated cottage, perfect for couples
  • Designer interiors
  • Hot tub
  • Fully air-conditioned

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£850pp
Total price £1,700
View details
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La Casa dei Mandorli

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic bijou Chianti villa
  • Stunning views
  • 10m private infinity pool
  • Beautiful sunset terrace
Reserve now for 2025 with a fully refundable deposit of £500

Use our Advanced Registration service to secure your 2025 holiday with a deposit of £500, 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
Reserve now for 2025 with a fully refundable deposit of £500

Use our Advanced Registration service to secure your 2025 holiday with a deposit of £500, fully refundable when prices are published

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A brand you can trust

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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-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

  • 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

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Holiday ideas

  • Holidays in Corsica
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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.

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