Here at Oliver’s Travels, we really like things quirky. It’s our philosophy that when you go on holiday, wherever you’re staying should be just as beautiful and memorable as the country you’re visiting. With us, you can forget the sterile magnolia walls and tiny kettles of your average chain hotel. We’re always on the lookout for luxury villa rentals that’ll really blow your flip-flops off.

Ever fancied a stay in a windmill, a sea fort, an observatory or even a submarine? We’ve got them all, and more besides! We’ve put together our top ten favourite properties that are crazy, quirky and just plain fun… It’s like we always say – why do ordinary?

1. Lovers Deep

Lovers Deep - Luxury Villas - Caribbean- Oliver's Travels

Lovers Deep, Caribbean- Oliver’s Travels

Location: Caribbean

Sleeps: 2

Price from: £87,500 pppn

Quirkiest Feature: Lovers Deep submarine is the most luxurious and exclusive property in our collection, a unique leisure submarine intended for couples who want to have a private night together submerged beneath the ocean waves.

2. Moroccan Lodge

Moroccan Lodge - Morocco - Oliver's Travels

Moroccan Lodge – Morocco – Oliver’s Travels

Location: Morocco

Sleeps: 25

Price from: £86 pppn

Quirkiest Feature: The sumptuous decor is full of Moroccan charm, with draped ceilings and plenty of places to lounge around! The swimming pool is amazing too, and styled around a jungle lagoon.

3. Napoleonic Fortress

Napoleonic Fortress - South East - England - Luxury Villas - Oliver's Travels

Napoleonic Fortress, South East – Oliver’s Travels

Location: The South East Britain

Sleeps: 18

Price from: £306 pppn

Quirkiest Feature: The £3 million refurbished Fort, once designed to protect Portsmouth, is now offering an exclusive and private retreat. There’s no other venue like it – for a lasting impression, this is the place!

 4. C17th Castle

C17th Castle, Somerset - Luxury Villas – Oliver’s Travels

Location: Somerset, The South West, Britain & Ireland

Sleeps: 16

Price from: £58 pppn

Quirkiest Feature: The Castle is a Grade II listed detached hill top property overlooking the wooded North Somerset countryside on one side and across the Bristol Channel to Wales on the other.

5. Anemómylos

Anemómylos - Mykonos - Greece - Luxury Villas - Oliver's Travels

Anemómylos, Mykonos – Oliver’s Travels

Location: Mykonos, Greece

Sleeps: 4

Price from: £131 pppn

Quirkiest Feature: Traditional Mykonian windmill converted into a practical pied a terre and ideally positioned for access to all the town’s must-sees and must-dos! 

6. Chevaliers Gatehouse

Chevaliers Gatehouse - Midlands - England - Oliver's Travels

Chevaliers Gatehouse – Midlands – England – Oliver’s Travels


Location: Midlands, England

Sleeps: 4

Price from: £44 pppn

Quirkiest Feature: This Elizabethan gatehouse was once slept in by Prince Rupert, he is celebrated in the hanging tapestries throughout the property.

7. Roccia Di Corte

Roccia di Corte, Lazio - Oliver's Travels

Roccia di Corte, Lazio – Oliver’s Travels

Sleeps: 8

Price from: £85 pppn

Quirkiest Feature: It’s on the top of a gigantic mountain, surrounded by even morr mountains! Part Tolkien fantasy castle, part supervillain lair, it can only be accessed by a land bridge with breathtaking views.

8. Chateau De Baloigne

Chateau de Baloigne - Rhone-Alpes - Luxury Villas - Olivers Travels

Chateau de Baloigne, Rhone-Alpes – Olivers Travels

Location: Rhone-Alpes, France

Sleeps: 12

Price from: £29 pppn

Quirkiest Feature: The property is set within the ruins of a medieval castle, with some parts of the original dungeon dating back to the 12th century.

9. Villa Trullo

Villa Trullo - Puglia - Italy - Oliver's Travels

Villa Trullo – Puglia – Italy – Oliver’s Travels

Location: Puglia, Italy

Sleeps: 8

Price from: £91 pppn

Quirkiest Feature: The beautiful conical roofs of Villa Trullo are truly unique to the region. This serene property is perfectly suited to people seeking a beautiful hideaway in peaceful surroundings.

10. Castelnau De Fezensac

Castelnau De Fezensac - Midi-Pyrenees – Luxury Villas - Oliver’s Travels

Castelnau De Fezensac, Midi-Pyrenees – Oliver’s Travels

Location: Midi-Pyrenees, France

Sleeps: 80

Price from: £71 pppn

Quirkiest Feature: Have you ever dreamed of having your very own 13th Century village? Here is the chance to rent a Medieval stronghold with 12 fully furnished houses and private gardens, right in the heart of Gascony.

Every great escape starts with finding the perfect property to suit all your needs. With over 2,000 villas to choose from, our Top 10s shortlist the best of the best. If you need help finding the perfect fit for you, give our concierge team a call.

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