Simpson Travel Villa Holidays

Considering a villa holiday in 2026? For couples, groups, friends and families, villa holidays are an ideal way to make the most of your holiday destination, giving you maximum flexibility and privacy, plus the chance to enjoy a more authentic local experience. Our villa holidays give you exclusive use of your own space, with the reassurance of knowing that our friendly local concierges are just a phone call away.


Where will your next villa holiday take you?

Villas in Greece
From the history and majestic scenery of Crete to the idyllic boats-and-beaches charm of the Ionian islands and Skopelos, not forgetting Sivota and the Peloponnese on the mainland, our collection offers you almost 200 villas in Greece.

Villas in Turkey
For luxury villas at a competitive price, it has to be Turkey. Choose Kalkan for superb quality accommodation, fantastic restaurants and a beach club vibe, or pick a villa on the Bozburun peninsula, Islamlar or Akyaka for a more authentic Turkish holiday atmosphere.

Villas in Corsica
The Med's best kept secret, Corsica is an inspired choice for your next villa holiday. Think pristine sandy beaches, high mountains and perfectly clear sea; all you have to do is pick your favourite luxury villa in Porto Vecchio, Bonifacio, the Valinco Gulf, L'Île Rousse or Calvi.

Villas in France
Our France portfolio spans the country's best holiday villa hot spots. Idyllic Île de Ré is quietly chic and family friendly, while Hossegor and Biarritz bring a livelier, surfy feel. Provence and the Dordogne are enduring classics that will always enchant.

Villas in Mallorca
From traditional fincas to five-star luxury villas near Pollensa, Mallorca is a wonderful destination for families, groups and couples; in short, anyone who loves beautiful beaches, traditional towns, a lively little capital and fabulous food.

Villas in Italy
The home of (arguably) the world's greatest art and cuisine, with a stunning coastline and incredible cities, it's hard to imagine a better base for a villa holiday, from the cultural power houses of Tuscany and Umbria to the sunny beaches of Puglia and Sicily.

Villas in Portugal
Villa holidays on the Algarve are simplicity itself, with short transfers, a great climate and a wide choice of properties for families and groups. Let us help you choose a villa near the best golf courses and beaches on this deservedly popular southern Portugal coast.

 


What kind of villa holiday are you looking for?

Something for couples
If you thought a villa holiday was only for big groups, think again! We have over 130 cottages, studios and villas with pools ideal for two, so whether you’re looking for honeymoon luxury, romantic seclusion, a base with lots to do, or all three of these and more, we have one to to suit you.

Beachfront bliss
The vast majority of our villas have private pools, but if you prefer to feel sand between your toes and salt on your skin, we have a range of properties where the sea is just moments from your front door.

A little bit of luxe
Luxury means different things to all of us, but if you’re looking for a villa holiday where the comfort and facilities levels are the very best available, you’ll find it in our Signature collection. From houses with tennis courts and home cinemas to villas with direct beach access as well as private pools, these properties are exceptional, with service levels carefully tailored to match.

With friends & large groups
Organising a group villa holiday can be challenging, but booking a villa with a pool is a very cost effective way to enjoy a holiday with several generations or a group of friends. Look out for villas with guest annexes for those that need extra privacy, and consider houses within walking distance of local facilities so everyone gets to holiday at their own pace.

Car-free villas
If you spend a lot of time driving at home, or just like to enjoy a glass or two of wine with your meal out, a car-free villa holiday is the one for you. Choose from over 80 properties across our collection.

Villa holidays with flights
Are you looking for a villa and flight package? Over 65% of our properties are priced with the best available flights as a package and some are priced as villa-only, allowing you greater flexibility for your holiday.


Still not sure? Browse our villa holiday categories below for even more inspiration and a huge selection of villas with pools.

Quotes
  • We found Villa Mantilari excellent and exceeded our expectations in terms of quality and facilities. We celebrated a 70th birthday with 16 adults. Everything went smoothly and the Simpson’s Rep and owner were quite excellent. Highly recommended for a group or large family get together.

    Mr John McLauchlan, Mantilari Estate, Crete

  • What an amazing place Villa La Piste and Capbreton is. Somewhere where you can forget your every day and live for the moment - surf, cycling instead of the car and great food - what’s not to like? The host is the owner and the villa is exceptional - and what a position! We didn’t use our car once in the week we were there. We would have happily stayed longer.

    Ms Susan Webster

  • "We have just enjoyed one of the greatest holidays of our life. Trullo Ashi was absolute bliss - an incredible property, beautiful views, so clean, the pool was a dream, and the location was amazing - so many glorious places to visit nearby. Excellent service from Simpson too - we can't wait to return next year!!!"

    Mr T Worsley, Trullo Ashi, Puglia