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Luxury villas, boutique Simpson Hotels and unforgettable holidays

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Villa holidays for couples

Whatever holiday you’re dreaming of, our villas for two offer the perfect base for a memorable trip. Whether you’re seeking a luxury villa with a private pool, an intimate hideaway just moments from the shore or a cosy bolthole with tavernas and shops on your doorstep, our portfolio has the perfect solution. With a superb selection of smaller villas, promising privacy and independence both on and off the beaten track, you’re sure to find the holiday you’ve been yearning for.

The magical pine forests of the Bozburun Peninsula and the chic rooftop bars of Kalkan are a paradise for those seeking romance and the exceptional quality of our Turkish portfolio continues to offer excellent value.

The legendary beauty of the Greek islands is unrivalled. Mystical landscapes, vibrant towns and a stunning coastline of hidden coves, ancient fishing villages and irresistible waterside tavernas are the key to its enduring appeal.

You don’t need to fly to the other side of the world to enjoy an idyllic holiday for two, with Corsica offering pretty hillside cottages and sandy beaches to rival anywhere in the Caribbean.

From enchanting trulli houses to charming countryside retreats, our Italian villas promise stunning scenery and the opportunity to experience something a little different with a taste of la dolce vita.

Mallorca is renowned for its flawless beaches and historic towns. Meander the cobbled streets and stop off to enjoy a little tapas or wander home for a candlelit supper under the stars. Even some of our more petite properties here feature spacious terraces and serene gardens, so you can dine al fresco like the locals.

Foodies and thrill-seekers will love the diversity of our French portfolio. Whether you’re seeking an authentic rural hideaway or the glitz and glamour of a lively seaside town, we have villas in France to satisfy all tastes.

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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 14 October 2023

Accommodation Only

  • Villa

Prices
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$644pp Total price $1,288
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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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Villa Athina

Lefkada, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Close to Agios Nikitas
  • Wonderful sea and mountain views
  • 20 min walk to village
  • Cosy and comfortable

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

Accommodation Only

  • Villa

Prices
from

$654pp Total price $1,307
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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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Villa Valia

Lefkada, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Close to Agios Nikitas
  • Cosy and comfortable
  • Wonderful sea and mountain views
  • 20 min walk to village

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

Accommodation Only

  • Villa

Prices
from

$654pp Total price $1,307
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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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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 14 October 2023

Accommodation Only

  • Villa

Prices
from

$657pp Total price $1,313
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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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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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Stella Cottage

Kefalonia, Greece

Villa | Bedroom 1 | Sleeps 2

  • Seafront cottage
  • 20m to water's edge
  • Beautiful sea views
  • Fiskardo 12min walk

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

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  • Cottage

Prices
from

$660pp Total price $1,319
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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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Villa Aetos

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Tavernas and mini-market 5min drive

Prices are based on 2 sharing for 7 nights on Tuesday 2 May 2023

Accommodation Only

  • Villa

Prices
from

$682pp Total price $1,363
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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Sivota Senses – Villa Amalia

Sivota & Epirus, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Innovative contemporary villa
  • Light and spacious
  • Sandy beach 5min walk
  • Sivota harbour 10min walk

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

Accommodation Only

  • Villa

Prices
from

$685pp Total price $1,369
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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Sivota Senses – Villa Loukas

Sivota & Epirus, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Innovative contemporary villa
  • Light and spacious
  • Sandy beach 5min walk
  • Sivota harbour 10min walk

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

Accommodation Only

  • Villa

Prices
from

$685pp Total price $1,369
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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Villa Almyra

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Short drive to tavernas

Prices are based on 2 sharing for 7 nights on Tuesday 2 May 2023

Accommodation Only

  • Villa

Prices
from

$688pp Total price $1,375
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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Villa Kambos

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Short drive to tavernas

Prices are based on 2 sharing for 7 nights on Tuesday 2 May 2023

Accommodation Only

  • Villa

Prices
from

$689pp Total price $1,378
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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Why travel with us..?

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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
  • Villas in France
  • 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

    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

    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 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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    • 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

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    • Why Simpson Travel?
    • Travel arrangements
    • Advance Registration
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    • Loyalty Club
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