We always like to keep things interesting here at Oliver’s Travels. It’s our philosophy that when you go on holiday, your accommodation should be just as memorable as the place you’re visiting. With our holiday homes, you can forget the sterile magnolia walls and tiny kettles of your ordinary chain hotel. Instead, our ever-growing portfolio is full of 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 it all, and then some! To show you what we mean, we’ve put together a list of our top ten quirkiest villas that are especially unique and different. It’s like we always say – why do ordinary?

Cortijo Don Cristobal

Sleeps: 8

Price from: £64pppn (based on occupancy of 8 people)

Just look at that location! Set right in the middle of an expansive vineyard, Cortijo Don Cristobal is an enchanting home in the hills that rise above Andalusia‘s Costa del Sol. The traditional hacienda-style home is built around a central courtyard that has a delightful plunge pool in the middle and swaying palms around its edge.

Inside, the design is classically Spanish, with a grand living room that makes a feature of the exposed wooden beams and terracotta tiled floor. Your party will love making use of the large kitchen and big group meals in the dining area.

The villa’s biodiverse vineyard produces delicious grapes which turn into the Amorous Goat wine. What’s more, guests are more than welcome to sample a few bottles during their stay at the property! This home is also part of our Sustainable Collection, not only due to use of its own on-site produce, but the owners are also committed to using renewable and green energy during your stay.

2. Chateau Des Poetes Keep

Chateau Des Poetes Keep
Sleeps: 10

Price from: £34pppn

The artful Chateau Des Poetes Keep and its fascinating architecture date back over 900 years, to the 13th century. It sits in the enchanting Loire Valley, acting as both B&B, private residence and luxury holiday home. It can be rented independently, or along with its medieval sister wing, Chateau Des Poetes Pavilion.

The interiors of the Keep are tastefully decorated with rich tapestries, chandeliers and antique furniture on all four floors. Even the bedrooms are made up of luxurious bedding to complement the views of the valley. In the dining room, you’ll find a warming fireplace, and all around the house, you’ll run into special little gems like a piano, a library and a games room.

In the 15 hectares of private parklands that go along with the castle, you’ll be able to enjoy a splendid French garden and wander around ancient castle ruins. The grounds are filled with exotic trees from all corners of the world, and there are even a private pond and a pool… Perfect for those long sunny days in the South of France.

3. Chateau De Baloigne

Chateau De Baloigne
Sleeps: 15-18

Price from: £26pppn

For those seeking comfort, character, style and an atmosphere unique amongst our collection, then this medieval castle is the perfect choice for your luxury château holiday. Château De Baloigne, and indeed the whole estate, is protected by the government as a Historic Monument. However, the ancient building has been combined with 21st-century touches such as a fully fitted kitchen, hot and cold running water and modern bathrooms with showers. The interior décor is traditionally French but with a few Spanish touches.

This fabulous self-catering chateau is surrounded by medieval ruins providing a truly atmospheric holiday experience. There are multiple great spots to relax and while away the hours either reading or enjoying a glass of wine on the terraces overlooking the woodland. The views in every direction are just stunning. You are in the heart of nature surrounded by pine trees with the river running below.

Quite simply a magical, unique experience. I can’t impress upon you or emphasize this enough – the photos do not do it justice.

4. Faro Rosso

Faro Rosso
Sleeps: 12

Price from: £229ppn

Faro Rosso, located at the southernmost tip of Sardinia in the coastal region of Chia, is a striking lighthouse building turned exclusive holiday home. It was initially built in the 1850s, and its light still guides ships to safety to this day. You’d be hard-pressed to imagine a more idyllic place from which to take in the beauty of the region than Faro Rosso, where the panoramic ocean views are truly breathtaking.

The top-class accommodations of this lighthouse are set over four levels, containing four suites in the main building and two further apartments in the converted military barracks on the property. The impressive skylights on the first floor make the rooms here especially ideal for those seeking romance, as you can just rest your head on the pillows and find yourself gazing right up at the stars.

Some of Faro Rosso’s most beautiful gems and best-kept secrets include the ocean views from the infinity pool, the impressive collection of Italian wines and champagne kept in the cellar, and the secret path that leads to the main lightroom. And if that’s still not enough to entice you, there is also a gorgeous sun terrace right on the lighthouse roof.

5. The Exclusive Village

The Exclusive Village
Sleeps: 50-80

Price from: £127pppn

In the historic heart of Gascony, built atop a rocky spur, is the one-of-a-kind luxury accommodation known as The Exclusive Village. It is indeed a private village, and it dates all the way back to the 13th century. Complete with fourteen unique and beautiful houses, a private church and spectacular gardens, the village and its quaint winding streets offer some of the region’s best views of the Midi-Pyrénées landscapes.

Each of the village houses has been restored and decorated with its own individual style. Within their honey-coloured limestone walls, the homes are adorned with antiques and fabrics dating back to the village’s original era. These tasteful designs have been featured in publications like Vogue, Elle Décor and Condé Nast Traveller, and are a source of inspiration for artists, designers and travellers alike.

As it can accommodate as many as 80 guests and is home to a stunning private church, The Exclusive Village is a natural venue for weddings and special events. There is even a vaulted 180m² reception room and enough space among the fruit trees in the garden to dance the night away. That’s what we call a party.

6. Ardentallan Cottage

Ardentallan Cottage

Sleeps: 4

Prices from: £50pppn

The epitome of tranquillity, Ardentallan Cottage is the ultimate break from the world. The sea views are breathtaking come rain or shine; the landscape here really is ever-changing! Although it feels completely remote, there is a nearby restaurant and shops within a short drive. 

If you are looking for a retreat from the world, for nature’s muse and for a first-hand experience of the wilderness of Scotland, then Ardentallan Cottage is the right place for you. The house itself is comfortable and cosy, with deep walls and window nooks, making it feel safe and sheltered. Recently renovated, the house is immaculately decorated, with clean white walls and all the modern conveniences you could need. 

Completely undisturbed, there is a complete sense of tranquillity, that makes relaxing second nature. Whether you are looking for creative inspiration, for an active holiday, or simply for some quiet time as a family, Ardentallan Cottage is the perfect place; a unique holiday home that you will never want to leave.    

7. Trulli Di Olive

Trulli Di Olive
Sleeps: 8

Price from: £49pppn

Tucked away in a tranquil olive grove, Trulli Di Olive is a one-of-a-kind holiday home where past and future blend seamlessly. The original Pugliese Trulli has been renovated with the highest attention to detail and interconnected with modern structures using stylish designer-iron industrial fixtures and fittings. The luxurious, modern interiors accent the rustic stone walls and traditional furnishings perfectly.

The centrepiece of the Trulli is its state-of-the-art common room – a glass cube which has been created as the perfect spot to relax, gather and gaze out at your surroundings. Just like the rest of the property, the cube room is connected to other parts of the house by a network of above-ground tunnels.

Right on the Trulli grounds, you’ll find a private 20-metre-long saltwater pool among the olive trees. There is also a unique outdoor cooking area with a quarry-stone barbecue and wood-burning stove oven for when everyone wants to gather around a home-cooked meal. For other days when you’re feeling a bit more adventurous, beautiful beaches and towns like Ostuni and Alberobello are just a short drive away.

8. Treasure Island

Treasure Island
Sleeps: 14-20

Price from: £188pppn

Magical, spectacular Treasure Island is a private island in the Cyclades that exceeds all expectations of what holiday homes should look like. The property spans 900 acres of Mediterranean landscape surrounded by glistening turquoise seas. It is authentically Greek and fabulously lush, sure to make all your dreams of a paradise isle come true.

Treasure Island has been in its owner’s family for over a hundred years. When they bought it, they also built a neoclassical mansion right on the beach, transforming the island into a luxury getaway. The building’s terraces face every direction, making it easy to find the ideal sunny spot to take in the ocean landscapes and relax. Inside, you’ll find bright rooms with tall ceilings and windows that let in lots of light. Each bedroom has a marble en-suite bathroom, and the master suite comes with a private terrace and wood-burning fireplace.

There is organic produce grown right on the island, meaning fresh fruit and vegetables are available every day. There is, of course, a private chef available but if you prefer to cook your own meals you should definitely try your hand at the barbecue area and dine alfresco under the stars.

9. Tour St Therese

Tour St Therese
Sleeps: 6

Price from: £18pppn

The perfect escape, Tour St Therese is ready to welcome you into its romantic fold. Say goodbye to high-tech gadgets: instead, lucky guests will find books, games, and a roaring fire for sitting beside as you enjoy them. Located next to a historic church, this storied holiday home offers an assured peaceful stay, with the only sounds coming from cuckoos and frogs and perhaps an owl come nightfall.

By day, enjoy a relaxing walk through the surrounding woodland or fields, coming home to prepare yourself a feast in the semi-circular kitchen. However, should you wish to venture into the nearby village, the owner is also on hand to arrange evening meals for you.

10. C17th Castle

C17th Castle
Sleeps: 16

Price from: £65pppn

With the woods of North Somerset on one side, and Wales across the Bristol Channel on the other, C17th Castle is a Grade II listed hilltop property with 360-degrees of some of the most beautiful landscape in Britain. As its name suggests, this castle originates from the 17th century and remains ever the fairy-tale destination.

Special celebrations like weddings, as well as holidays and even corporate events, are a perfect fit for this uniquely octagonal keep and eight surrounding turrets. The main keep consists of four levels and is positioned in the centre of a lush lawn and cobblestone courtyard. There are spaces perfect for large parties to dine and dance, as well as eight self-contained bedrooms.

The castle’s indoor pool can be reached by either of its two patios. One sunken patio with a rustic wooden hot tub, and a second private patio area which is perfect for barbecue evenings. All these spaces are made for socialising and enjoying each other’s company, no matter the occasion.

These are some of our favourite quirkiest villas, but you can find more in our Quirky and Characterful Collection. Every great escape starts with finding the perfect property to suit all your needs. With over 3,000 villas to choose from, our Top 10 Shortlists are 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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