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 – from Alpine chalets to vineyard haciendas, and private islands to ancient fortresses and even a whole village… ’cause why not? 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?
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 the use of its own on-site produce, but the owners are also committed to using renewable and green energy during your stay.
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.
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 emphasise this enough – the photos do not do it justice.
Sleeps: 10
Price from: £337pppn
An escape to the Alps is always a good idea, and where better than well-heeled Val d’Isère to call home in the mountains? Chalet St Roch is a beautiful mountain lodge with room for 10 guests to live in understated luxury. Inside is a comforting and warming palette of wood and stone accents that you can sit back and enjoy while the private chef prepares dinners.
But the pièce de résistance has to be the glorious indoor swimming pool carved straight into the rock face. Hop between the pool and hammam for heating and cooling rejuvenation, the perfect antidote to sore limbs from snowy daytime activities.
As we said, an escape to the Alps is always a good idea. And we mean always… just check out our fabulous Alpine chalets that are available during summer that make for the perfect place to stay on an adventure holiday once the snow has melted.
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.
Sleeps: 6-12
Prices from: £425pppn
Sleeps: 20-22
Price from: £395pppn
Perched on the picturesque St. Elia Ridge, Castello Salentina offers a charming retreat in the heart of Puglia. Nestled along Via Andrano, known locally as “the Vale of Health” for its rejuvenating air, this stunning estate is just a 15-minute drive from Lecce, often dubbed “The Florence of the South.” Its prime location also provides easy access to Puglia’s breathtaking coastlines along both the Ionian and Adriatic seas.
The estate accommodates up to 22 guests across four distinct areas: the Castle, Cottage, Tower, and Masseria. Upon entering the Castle, guests are welcomed by a seamless blend of historical elegance and modern comfort. Two spacious lounges offer the perfect setting for relaxation, while a Beckstein Grand piano invites impromptu performances. The Castle also features a fully equipped kitchen and an elegant dining room, perfect for culinary gatherings and shared meals with loved ones.
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.
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 to sit 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.
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 landscapes 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.
Quirky converted homes in the UK
Top 10 quirky chateaux in Southern France
The quirkiest chateaux in France
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