At Oliver's Travels, we bring the magic of multigenerational holidays to life. Our carefully curated collection of villas is designed to cater to every member of your family, from little explorers to long-time adventurers. Whether you're planning a family reunion, a big group getaway, or a special celebration, our villas offer the perfect blend of privacy with shared experiences, and luxury with familiar comfort.
Found in some of the world's most idyllic locations, our villas provide ample space for everyone to relax and enjoy. For the little ones, we offer a range of kid-friendly amenities, including playrooms, games, and pools with safety features, ensuring they have a blast while the adults unwind.
Grandparents will appreciate the thoughtful touches that make their stay comfortable and stress-free, such as accessible facilities and serene spaces for quiet moments. Many of our villas are equipped with modern conveniences and thoughtful design, making them perfect for families of all ages.
Create lasting memories with Oliver's Travels, where multigenerational holidays are not just a dream but a reality.
Style and character are everything at Oliver’s Travels, and our collection of handpicked villas for large families have this in spades. Our destination experts curate unique homes in beautiful locations that are perfect for families and groups, and are guaranteed to ‘wow’.
Once you book a holiday, the service doesn't stop there. Our Concierge Service means you'll be in good hands to arrange pre-arrival fridge stocking, tours and activities, car hire, airport transfers and so much more, to make your stay truly extraordinary.
As of 2025, for the first time in history, there are up to 7 generations that can make up a family:
The Silent Generation: Born 1928–1945
Baby Boomers: Born 1946–1964
Generation X: Born 1965–1980
Millennials (Generation Y): Born 1981–1996
Generation Z: Born 1997–2012
Generation Alpha: Born 2013–2024
Generation Beta: Born 2025 onwards
Take a look at these example experience itineraries that are perfect for all the family. Seen something that appeals? When you've booked your dream multigenerational family villa holiday, contact our Concierge Service to make these travel adventures a reality!
Step into a fairytale with a private chateau rental! Explore grand halls, secret passages, pepper-pot turrets and lush gardens. Enjoy medieval feasts, storytelling, and themed activities for all ages. Kids become knights and princesses, while adults unwind in regal luxury. An unforgettable, magical experience awaits!
Connect with gentle giants at a renowned elephant sanctuary, feeding and observing them in their natural habitat. Then, immerse yourself in local culture by exploring sacred temples, admiring intricate architecture, and witnessing serene rituals before cooling off in dreamy turquoise waters. A day of awe-inspiring encounters and deep cultural discovery awaits!
Embark on a thrilling safari at a nearby reserve, spotting majestic wildlife in their natural habitat. Afterwards, unwind at a picturesque vineyard, savouring a gourmet lunch and fine wines. Kids aren’t left out though - they’ll stay entertained with fun activities in beautiful grounds, making it a perfect day for all!
The Italian Lakes offer the perfect mix of adventure, relaxation, and culture for all the family. Explore Lake Como, Maggiore, and Garda on private boat tours, visit castles, and enjoy activities like pasta-making, truffle hunting, and vineyard tours. For adventure, try canyoning, cycling, or cable car rides. Stay in luxury lakeside villas, savour gourmet cuisine, and experience fabulous excursions like gelato-making and scenic train rides.
Set sail on an island-hopping adventure across Greece. Enjoy leisurely boat trips, savour fresh seafood lunches on deck, and dive into crystal-clear waters for colourful snorkelling experiences. Treasure Island is a gem in our portfolio - a private islet with a neoclassical mansion at its heart - the perfect place from which to explore hidden coves and sun-drenched shores on this idyllic escape.
Nothing is more magical for children than exploring a winter wonderland straight out of a fairytale, with snow-capped mountains, dense forests and frozen lakes. Something the whole family will never forget is watching the dazzling Northern Lights dance over the skies above, a memory that will last a lifetime.
Have a desert adventure that will thrill all generations. Enjoy immersing yourself in bursting culture with the Marrakech souks, marvelling at the colourful spices, Aladdin lamps, and beautiful carpets. Then venture out to the desert for camel rides across the dunes, visits to traditional Berber houses and memorable evenings spent under the starry skies.
Your dream holiday, effortlessly tailored. Our dedicated Concierge Service takes care of every detail, from your initial vision to the final touches, ensuring a seamless experience.
Simply share your ideas, and we’ll craft a bespoke getaway that’s uniquely yours.
This striking Mediterranean estate comprises two luxurious villas, each with eight en-suite bedrooms, with room for up to 32 guests. Ideal for events like weddings or reunions, the estate features expansive entertainment areas, four pools (two of which are shallow, perfect for little paddlers), a private bay with anchorage, and an on-site chapel, all within walking distance of beautiful beaches.
Moonstone Villa, nestled in the heart of the Cotswolds, offers a stunning retreat for up to 18 guests. With elegant Georgian design, sprawling grounds, and luxurious amenities, it's perfect for both relaxation and celebration. Whether hosting an intimate gathering or a special event, this exquisite property blends charm, style, and space for all the family to make memories in.
This charming villa set among the rolling hills of inland Andalusia makes for a delightful, private getaway for up to 10 guests. Featuring expansive outdoor spaces, including a private pool and lush gardens, its tranquil ambience make it an ideal setting for relaxation and special get-togethers. Just imagine sunset dinners on the terrace with your nearest and dearest.
Windermere Gothic Mansion, on the shores of Lake Windermere, is a grand Victorian mansion for up to 36 discerning guests. Its expansive grounds and versatile spaces make it ideal for large groups seeking a luxurious retreat. The mansion's blend of historic charm and modern amenities ensures a memorable stay for all. Just imagine the Murder Mystery parties that could take place here…!
Nestled in the Luberon region of Provence-Alpes, this magnificent villa complex offers an exceptional retreat for large groups of up to 24 guests across its three beautifully restored stone homes. The estate features expansive grounds with two swimming pools, a tennis court, and a boules pitch amidst lavender fields, providing ample space for relaxation and recreation.
Villa Carli is a magnificent Tuscan retreat oozing old-world sophistication with contemporary touches. This stunning villa boasts 16 beautifully appointed bedrooms, vast grounds, and exquisite outdoor areas. With a private pool, elegant dining spaces, and panoramic views of the countryside, it offers the perfect backdrop for unforgettable events and celebrations of up to 32 guests.
This stunning 15th-century château in the Dordogne offers a magical retreat for families and groups. The château features historic interiors with period details, including original tapestries and paintings ans is surrounded by 30 hectares of parkland, where guests can enjoy a swimming pool, orangery, and formal lawns. Its proximity to charming villages and the city of Bergerac enhances the experience.
Barons Tower, a Grade A-listed Peel Tower in the Scottish Borders, offers something rather different for a group getaway. This fabulous fortress has been meticulously restored to blend historic charm with modern luxury. The beautiful grounds feature a walled garden, croquet lawn, and panoramic views of the Ettrick Forest, providing an atmospheric backdrop for family gatherings and celebrations.
Step into the pages of history at Castello Maddalena, a captivating 11th-century castle set among the lush green landscape of Umbria. Perfect for multigenerational families, this grand estate invites you to live like royalty with ten luxurious bedrooms, a private heated pool, and lush gardens. Its rich heritage, stunning views, and ample space make it an unparalleled setting for family gatherings.
Located within the luxurious VILA VITA Parc Resort in the Algarve, this villa is the ideal getaway for multigenerational families, offering five en-suite bedrooms, an infinity pool, and stunning ocean views. Imagine gathering for sunset dinners on the terrace with the glow of lamps and that magnificent outdoor fireplace. What's more, the resort’s amenities—beaches, fine dining, a spa, and kids facilities—make it a perfect getaway to suit all the family.
Villa Plaka Danae, a newly built luxury villa in Plaka, Crete, offers breathtaking views of the Elounda Gulf and Spinalonga Island. Designed for up to 10 guests, it features five elegantly appointed bedrooms, each with en-suite bathrooms. The villa boasts sophisticated interiors, a state-of-the-art gym, a hammam, and a stunning infinity pool. Its prime location provides easy access to the charming village of Plaka, known for its traditional tavernas and warm hospitality.
Villa Bolero, nestled within the exclusive Casa de Campo resort in the Dominican Republic, offers a vibrant Caribbean retreat for family groups. This six-bedroom villa comprises a private pool, and hot tub, lush green lawns, and spacious gazebo with a mini-kitchen and bar providing an ideal setting for family gatherings. Guests can take advantage of the resort's amenities such as a spa, fitness centre, marina, private beach, and world-class golf course right on your doorstep.
