August might appear to represent the end of summer, but don’t believe the baloney. The most-touristed continent on Earth (Europe FYI) saves its true charms for September where temperatures fluctuate between a wonderful 25°C to 32°C, streets are quieter but the sea is still the perfect temperature for a swim. For most travellers, the ninth month is a back-to-reality wake-up call, but if you can buck the trend, you’ll find September is the best time to travel. Don’t let the opportunity pass you by, take advantage of the plummeting prices and you’ll reap the rewards of crowd free beaches, queueless restaurants and diminishing traffic jams. Below you’ll find the very best regions to go on holiday in September, alongside our top villa picks that are perfect for couples, groups, and families travelling with infants. Happy travels.

1. Pretty Puglia

Puglia, Italy

How hot are we talking? You’ll be chuffed to know that September is, in fact, the last summer month in Puglia, so it’s deffo prime time to visit this enchanting region. Enjoy warm to even hot afternoons, especially at the beginning of the month, with an average high temperature of 25°C. The nights are also gloriously warm, sticking to around 16°C. Though incredibly decent, opt for packing a pashmina or two – versatile and incredibly light weight, it’s the perfect accompaniment for an evening stroll.  

Why go? Puglia is the Italian region on everyone’s lips, a retreat where savvy travellers bored by the crowds of Tuscany and Florence turn to for a sweet escape, swapping the chaos for something more manicured and dainty. We could rave about this region all day long, but in short, Puglia is a pretty superb villa holiday destination.

The best villa…Trulli La Pietrina

Trulli La Pietrina - Puglia - Oliver's Travels

Trulli La Pietrina – Puglia – Oliver’s Travels

Just a stone’s throw away from from the stunning whitewashed town of Ostuni, Trulli La Pietrina is the go-to villa for those looking to immerse themselves in the Puglian culture. September is a cracking time to getaway and once you get a glimpse of the villas beautifully rustic interior you won’t need any extra persuading. The garden alone is a beautiful area to enjoy outdoor living; with  flourishing of plant-life, an opulent swimming pool and canope for shade. You couldn’t wish for better.

Sleeps: 6

Weekly rate in September: £1394

2. Adventurous Algarve

Beautiful beach with boats in Carvoeiro, Algarve, Portugal

Algarve, Portugal

How hot are we talking? Well, it’s not uncommon for temperatures to exceed 30°C in the Algarve, but on the whole, the average temperature throughout September is around 23°C – which is just enough to achieve a flawless sun-kissed glow.

Why go? Alluring tourists since the 60s, the Algarve is famed for its cliffs, scalloped bays and sandy beaches. But away from the resorts is a different story – the west coast is more serene and less about development, so you’ll get to experience the best of both worlds. September will also be much quieter and tourist free (well, almost!) compared to July and August. So if you’ve ever fancied a slice of Portugal’s offerings, September is a perfect time to visit.

The best villa…Vidamar Ocean Villa

Vidmar Ocean Villa - Algarve - Oliver's Travels

Vidamar Ocean Villa – Algarve – Oliver’s Travels

Both elegant and airy, Vidamar Ocean Villa is the ultimate abode to host your Portuguese escape. Great for couples or families with infants, you’ll adore every nook and cranny this villa has to offer. On the ground floor, you’ll find the essentials: kitchen area and lounge with patio doors leading onto your private pool area. Then upstairs you’ll find two modern bedrooms – both are ensuites and they come with complimentary toiletries.

Sleeps: 4

Weekly rate in September: £2,368

3. Charming Crete

Crete, Greece

Crete, Greece

How hot are we talking? The average daytime temperature drops from August ever so slightly to 24°C, but you can still expect high peaks reaching 27°C and lows dropping to 19°C. Though it’s a pretty gorgeous range to be dealing with; not unbearably hot, but still cool enough to wear your winning shorts and tee combo. 

Why go? Castaway beaches, seafront towns and warm blue lagoons, Crete is the sparkliest of the Greek Islands. We haven’t worked out what makes this island so special, but we’ve put it down to a mix of things, from the culture that encompasses the streets, all the way to the magical scenery. 

The best villa…Sea View Villas

Sea View Villa - Crete - Oliver's Travels

Sea View Villas – Crete – Oliver’s Travels

Although pictures speak a thousand words, we can’t write enough good things about Sea View Villas – it is truly spectacular. The interior has been carefully crafted to the tiniest of details, to capture the right combination of style and comfort. Personally, we think you’ll be a fan of the fully equipped terraces and verandas that offer plenty of room to soak up the sun in peace. And then there’s the huge pool which doesn’t need an explanation – it’s just heavenly. Overlooking the fascinating Cretan Sea, this villa provides all possible comforts for a unique holiday experience.

Sleeps: 8

Weekly rate in September: £3,577

4. Captivating Costa Blanca 

Costa Blanca, Spain

Costa Blanca, Spain

How hot are we talking? Autumn begins late September but the weather remains pretty at  25°C, on a good week you could even be looking at 28°C – not bad for a last minute tryst in the sun. 

Why go? The White Coast is one of Europe’s most visited areas and it’s no surprise as to why. For starters, the infamous beaches are honestly out of the world but then there’s also a variety of activities on offer. You can even head inland to explore the villages and towns, the bustling nightlife, or to pick up the local fishing skill. So much to do, so little time!

The best villa…Villa El Cid

Villa El Cid - Costa Blanca - Oliver's Travels

Villa El Cid – Costa Blanca – Oliver’s Travels

Eco-friendly yet ultra luxe, Villa El Cid boasts not one but five swimming pools, a tennis court, restaurant and pool bar. It’ll feel as though you’ve set foot in your very own resort – ah-mazing. If you’re bringing little ones along with you, you can relax knowing that there is a child-friendly pool (gated) for them to enjoy. Villa El Cid also benefits from discreet 24/7 security, so you won’t have to worry about a thing.

Sleeps: 4-12

Weekly rate in September: £2,394

5. Scenic Sicily

Beautiful old harbor with wooden fishing boat in Cefalu, Sicily, Italy.

Sicily, Italy

How hot are we talking? Not only is the weather resoundingly gorgeous in September, you’ll also get the benefits of an empty-ish island. Pack your bags because clear blue skies and temperatures of up to 26°C await. 

Why go? Whether you’re a history buff, food and wine connoisseur or you just love to lay in the sun – Sicily will most oblige. All your senses will be satisfied; this open-air museum is packed with incredible archaeological sites and dramatic nature – I mean volcanoes exploding into the night sky. It’d be a shame to miss out.

The best villa…Villa Lorena

Villa Lorena - Sicily - Oliver's Travels

Villa Lorena – Sicily – Oliver’s Travels

Crisp interiors, lush gardens and panoramic sea views, Villa Lorena ticks all the right boxes. A fabulous holiday villa for groups of mates looking to grab the Sicilian culture by the horns from the comfort of a pretty villa. Some of the highlights include a beautiful rustic kitchen, BBQ area and cooling swimming pool. And if you look hard enough you’ll find the cellar with bountiful bottles of local wine –  arguably the villas worst kept secret!

Sleeps: 6

Weekly rate in September: £1,820

6. Carefree Cyprus


How hot are we talking? Cyprus enjoys over 300 days of sunshine – I know, a bleak, dreary contrast to the UK. The average maximum temperature in September is 29°C and 24°C in the mountains. The days really are a scorcher but thankfully the temperature dips slightly in the evenings with an average temperature of 19°C.

Why go? If you’re into mythology then you’ll adore the birthplace of the Goddess of Love, Aphrodite. The island of love is steeped in history, contrasts in colourful landscapes, unbeatable weather and of course, you’ll never be more than a short drive from the sea or surrounding mountains. 

The best villa…Villa Anissa

Villa Anissa - Cyprus - Oliver's Travels

Villa Anissa – Cyprus – Oliver’s Travels

Simplicity is easier said than done, but Villa Anissa captures it effortlessly. A mix of nude and wooden tones; the shimmering blue waters of the Med and the marble flooring are all part of its appeal. This villa is perfect for those seeking lazy days in the sun, or anyone looking to expand their culinary prowess. Cypriot food is mouthwateringly good, so make the most of your very own private kitchen to whip up a local feast for your clan.

Sleeps: 4

Weekly rate in September: £2,905

7. Colourful Cote d’Azur

Cote d'Azur

Cote d’Azur, France

How hot are we talking? September marks the beginning of autumn in the Cote d’Azur, but there’s still enough sunshine to go around. The average temperatures fall to around 22°C and the evenings are still lovely sitting around 18°C. Don’t get fooled by these temperatures though and remember to pack heaps of suncream to avoid nasty burns. The lobster look is never OK.

Why go? Cliff-top roads, irresistible beaches and impossibly blue seas, the Cote d’Azur captures the South of France to a T – sexy, dripping in glitz and glamour. But you don’t need to be a high-profile celeb to make the most of the region, the never ending diversity is perfect for all kinds of travellers. 

The best villa…Villa La Garde

Villa La Garde - Cote d'Azur - Oliver's Travels

Villa La Garde – Cote d’Azur – Oliver’s Travels

Just a short drive from sunny St Tropez, Villa La Garde encompasses the heart and soul of the Cote d’Azur. Impeccable views of rolling hills, a stylish but cosy interior and an exquisite location to match, it’s got all the key components for any September getaway. You’ll feel miles away from the rest of the world, when in fact the local village is just a 10-minute walk away. It’s as easy as that!

Sleeps: 8

Weekly rate in September: £3,831

8. Luxurious Languedoc

Languedoc, France

Languedoc, France

How hot are we talking? Languedoc can be too hot (we mean sweating buckets hot), but September weather is exactly what you’re after. On average the temperature is around 25°C and in case you’re wondering, the water is 100% hot enough for a swim.

Why go? Languedoc is a delight to visit, more so because it’s completely off the cuff from the rest of the country. The French rural life is a pleasure we believe everyone should experience, even if just once. But if you’re not a fan of the countryside, don’t fret, Languedoc still has a mix of landscapes, a stunning coastline and lively social living. 

The best villa…L’Oustal Des Fleurs

L'Oustal Des Fleurs - Languedoc - Oliver's Travels

L’Oustal Des Fleurs – Languedoc – Oliver’s Travels

Flowers, flowers and even more flowers – I mean the name gives it away right? L’Oustal des Fleurs is an elegant 19th-century country house that exudes an unexplainable je ne sais quoi. It might have a little something to do with the outside haven of hammocks, loungers, dining tables, colourful flowers and stone barbeque that come together to create a cute area for all to enjoy.

Sleeps: 8

Weekly rate in September: £2,394

9. Incredible Ibiza

 Balearic Islands. Ibiza

Ibiza, The Balearic Islands

How hot are we talking? You’re looking at temperatures of 26°C, which is considerably cooler than August and July. By the end of the month, temperatures dip to 21°C,  so plan your trip wisely.

Why go? The clubbing capital of the world through and through, but holidaying in September shines a spotlight on Ibiza’s many other charms. The unfrequented coves, medieval history and pine-carpeted hills make this White Isle a force to be reckoned with.

The best villa…Villa Penelope


Villa Penelope – Ibiza – Oliver’s Travels

A great choice for a group of friends looking for some privacy to enjoy a holiday together. Though Villa Penelope is idyllically nestled in natural landscaped gardens, you’ll never be far away from the local amenities. During the day you won’t be able to resist the stunning swimming pool – so good you won’t get out till you’re all wrinkly. And then in the evenings, you can hit the town for sangria and tapas – the ultimate match made in heaven. 

Sleeps: 8

Weekly rate in September: £6,921

10. Sunny Sardinia 

Sardinia, Italy

Sardinia, Italy

How hot are we talking? With over 8 hours of sunshine per day, holidaymakers can enjoy an average temperature of around 22°C. Not too shabby for September! 

Why go? Visiting Sardinia will feel as though you have the whole island to yourself. And more importantly, the island isn’t one dimensional, rather it’s incredibly different, you’ll believe us when you see it with your own eyes. You’ll find the traditionalists in Barbagia, the high-life in Costa Smeralda and ancient history in Nora. The list goes on and on…

The best villa…Villa Capuccini

Villa Capuccini, Sardinia, Olivers Travels

Villa Capuccini – Sardinia – Olivers Travels

You’ll find this gem on the beautiful Costa Smeralda, within walking distance of shops, bars and moreish delicacies. This stunning villa has been given the love and attention it deserves and guests will unquestionably fall in love with this home, just as much as we have. The outside terrace is a treasure trove, great for drinking wine by the bottles and letting the head chef in your group tackle the mighty BBQ. 

Sleeps: 6

Weekly rate in September: £6,106

11. Coastal Cornwall

Cornwall, UK

Cornwall, UK

How hot are we talking? September is a great time to visit Cornwall, especially with the summer crowds going home. On average expect highs of 17°C and lows of 12°C, so pack a little of everything.

Why go? Naturally, we couldn’t talk about holiday regions without throwing in a staycation and Cornwall is the best region for a September holiday. Long stretches of sandy beach and jaw-dropping scenery, Cornwall feels miles away from the hustle and bustle of daily life, yet it’s easily accessible by car and train. 

The best villa… Sandcrest Cottage

Sandcrest Cottage - Cornwall - Oliver's Travels

Sandcrest Cottage – Cornwall – Oliver’s Travels

Enjoy peaceful seclusion taking in views of the charming coast from the private porch at  this spectacular cottage. Sandcrest Cottage is a perfect example of why UK breaks are equally good as jetting off to the Med; the cottage itself has been beautifully modernised with a unique, high-end design and finish. And the outside is equally as adorable – just picture yourself eating some scones and sipping your tea for breakfast – take me there now!!

Sleeps: 6

Weekly rate in September: £3,043

If you’re looking for more show-stopping holiday homes, check out our extensive portfolio of luxury villas that will have you grinning from ear to ear all year round. And if you need any extras or even some advice you can also call our concierge team.

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One Response

  1. Janette Nicholson

    I love your website and am planning a September Birthday vacation with just myself and a friend. The important things to me is weather, proximity to dining, must speak English, not far from an airport, and near by areas to tour. I don’t have a lot of time to research and it all depends on costs. I will be paying air and accommodations even though it my birthday. I can go anytime but keep in mind my birthday is 17 th ? Think not hot, and not cold. lol me to walk but need English speaking tours! I love THIS email regarding September vacations !


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