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 favourite properties that are especially quirky and different. It’s like we always say – why do ordinary?

1. Fortezza Di Spinola

Fortezza Di Spinola – Umbria – Oliver’s Travels

Sleeps: 10

Price from: £46pppn

The magnificent Fortezza Di Spinola used to be a fortress and a watchtower in medieval times. Today, it has been gorgeously restored as a luxury holiday home in the Umbrian countryside. It stands above the valley much as it did when it was built a thousand years ago, surrounded by olive groves and sunflower fields. It is entirely rural, yet no more than an hour’s drive from Perugia and three hours from Rome.

The luxury restoration hasn’t sacrificed the ancient character of the fortress, which is made up of two main buildings connected by a spacious terrace. You’ll be enjoying your stay amongst exposed stone walls, original terracotta tiling and furnishing that dates to the Baroque period. This traditional environment doesn’t come at the cost of modern luxuries, however. The courtyard boasts a lovely private pool, all five en-suite bedrooms come with orthopaedic mattresses, and the floors are comfortably heated.

Fortezza Di Spinola is not just a holiday home, however, but a spectacular venue for weddings and special events as well. There is even a honeymoon suite at the top of the tower which has a private terrace with unrivalled views of the region. It’s difficult to imagine anywhere quite as special to celebrate love.

2. Chateau Des Poetes Keep

Chateau Des Poetes Keep – Loire Valley – Oliver’s Travels

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 Pays de Loire, 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 with 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 a 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. Cooksbridge Chapel

Cooksbridge Chapel – Somerset – Oliver’s Travels

Sleeps: 8

Price from: £15pppn

The aptly named Cooksbridge Chapel, in the Somerset Levels village of Mark, is indeed an old Baptist chapel. Originally built in 1866, what stands today is a sleek and modern restoration which has kept the essence of its origins alive. The stone structure’s high vaulted ceilings are still intact, as are the stained-glass windows which completely transform the chapel’s interiors when the sun moves on its daily journey across the sky.

The bold character of the chapel is complemented by high-standard antiques and upcycled furnishings. These are just the beginning of a long series of nods to the property’s previous life, keeping it connected to its roots while offering all the modern luxuries of a twenty-first-century holiday home.

In the chapel gardens, you’ll find fruit trees and a large glass veranda, as well as a dining area in the vine-covered gazebo. These are an absolute dream come true after a long day of exploring the Somerset Levels; home of brilliant wildlife, great farmers market and (perhaps most importantly) cheddar cheese.

4. Faro Rosso

Faro Rosso – Sardinia – Oliver’s Travels

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 – Midi-Pyrénées – Oliver’s Travels

Sleeps: 50-80

Price from: £127pppn

In the very heart of historical 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 have 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. Napoleonic Fortress

Napoleonic Fortress – Hampshire – Oliver’s Travels

Sleeps: 18

Price from: POA

If you’re curious to venture about a mile or so off the coast of Portsmouth, you might be lucky enough to come across Napoleonic Fortress. Originally designed and built in the 1860s to protect the harbour from French invasion, the sturdy fortress still makes up something of a private island in the Solent. These days, however, it’s only used for private events and holidays to sea. Its views are one-of-a-kind, its privacy is complete, and its magic is very much real.

There are many original features of the fortress that have been carefully retained throughout its refurbishment. These include windows, vaulted ceilings and even gun emplacements, all of which ensure that luxury and history go hand in hand. Newer additions include a Champagne bar, a library, a gym, two rooftop sundecks, an open-air hot tub and a lighthouse – all within views of the iconic Spinnaker Tower across the water.

The fortress is accessed by boat and is just a quick two-hour trip from London. As such, Napoleonic Fortress makes the perfect venue for any special celebration. Be it birthday party or wedding reception; it will be a night to remember as you clink your glasses engulfed by a beautiful sunset at sea.

7. Trulli Di Olive

Trulli Di Olive – Puglia – Oliver’s Travels

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 – Peloponnese – Oliver’s Travels

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 across 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 let build 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 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. Roccia Di Corte

Roccia Di Corte – Umbria – Oliver’s Travels

Sleeps: 8

Price from: £104pppn

On a high perch above the Lazio landscapes, the ancient hamlet of Roccia Di Corte blends in beautifully with its surroundings and offers unbeatable 360-degree-views. What was once an Episcopal seminary in the fifth and sixth centuries, has now been restored to a relaxing holiday haven where its rural past is still very much alive.

The charm of centuries past is well captured in the preserved antique frescoes, and in the rooms, which have been tastefully furnished with antiques to keep in harmony with the local ambience. Guests also have access to a large garden and orchard which sits adjacent to the historic property, and the local village is accessed across a charming pedestrian bridge.

Roccia Di Corte has seen many a wedding through the years, as it is a beautiful and endlessly romantic destination in a lovely part of Italy. For the lovebirds, the in-house spa and Roman-style bathing thermae even offer special treatments for two. You might almost forget about the rest of the world. 

10. C17th Castle

C17th Castle – Somerset – Oliver’s Travels

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.


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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