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. Villa Cobalt, Sivota


Villa Cobalt – Sivota – Oliver’s Travels

Location: Sivota, Greece

Sleeps: 7

Price from: £111pppn

Quirkiest feature: The outside is a slice of heaven but the real quirkiness comes from the giant chess board that adds the fun factor! 

2. Faro Rosso, Sardinia 


Faro Rosso – Sardinia – Oliver’s Travels

Location: Sardinia, Italy

Sleeps: 12

Price from: £212pppn

Quirkiest feature: It’s a bloomin’ lighthouse – yes, yes you totally read that correctly! Honestly, this property is unlike no other, so if you have the cash to splash then Faro Rosso is the one for you. It’s already a given that Sardina’s scenery is already a knock-out, but the red vistas from the lighthouse tower really take things up a notch. You have to see it to believe it!

3. The Captain’s Fort, Hampshire


The Captain’s Fort – Hampshire – Oliver’s Travels 

Location: Hampshire, Britain & Ireland 

Sleeps: 44

Price from: £282pppn

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, Somerset


C17th Castle – Somerset – Oliver’s Travels

Location: Somerset, Britain & Ireland

Sleeps: 16

Price from: £57pppn

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. Bambu Luxury Tent, Andalucia


Bambu Luxury Tent -Andalucia – Oliver’s Travels

Location: Andalucia, Spain

Sleeps: 2

Price from: £211pppn

Quirkiest feature: Of course, it’s the tent! The decor is simply decadent but beyond that, it’s the little touches, such as the pillow-menu, beautiful bath tub and champagne reception that make this a hell of a contender. 

6. Chevaliers Gatehouse, Midlands

Chevaliers Gatehouse - Midlands - England - Oliver's Travels

Chevaliers Gatehouse – Midlands – Oliver’s Travels

Location: Midlands, Britain & Ireland

Sleeps: 4

Price from: £44pppn

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, Umbria

Roccia di Corte - Umbria- Oliver's Travels

Roccia Di Corte – Umbria – Oliver’s Travels

Location: Umbria, Italy 

Sleeps: 8

Price from: £109pppn

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

8. Chateau De Baloigne, Rhone-Alpes

Chateau de Baloigne, Rhone-Alpes - Olivers Travels

Chateau De Baloigne – Rhone-Alpes – Olivers Travels

Location: Rhone-Alpes, France

Sleeps: 12

Price from: £33pppn

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, Puglia

Villa Trullo - Puglia - Italy - Oliver's Travels

Villa Trullo – Puglia – Oliver’s Travels

Location: Puglia, Italy

Sleeps: 8

Price from: £109pppn

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, Midi-Pyrenees

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

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

Location: Midi-Pyrenees, France

Sleeps: 80

Price from: £75pppn

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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