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Dream Big: Exclusive-Use Resorts for Families & Friends in Sri Lanka and the Maldives

By Carly Watling on 24th September, 2025

Your secret weapon for group escapes…

If you’ve ever been tasked with planning a holiday for a big group of family or friends, you’ll know it can feel a little overwhelming.

Choosing the right place, making sure it works for everyone, and dealing with all the logistics is no small feat. That’s where we come in –  a Fleewinter travel specialist is your best friend. We help hard working group organisers like you find the perfect property that ticks everyone’s boxes.

To inspire your next big getaway, here are some of the most exclusive private-island and private-resort buy-outs in the ever popular Maldives and Sri Lanka. Think of this as your menu of magical hideaways but I will help you pick the one that suits your group best.

I can’t promise you discounts or cheap bargains in these countries — what I can promise is a selection of premium choices, designed for special occasions. If you’re looking for something exceptional for your special group holiday, then read on…

The Maldives: Your Own Private Paradise

Imagine stepping off a yacht into soft white sand, your children already racing ahead to find the best hammock, while friends gather on the deck with cocktails. The Maldives was made for this kind of escape, and these private islands take it to another level with outstanding service and idyllic endless beaches.

Ithaafushi – The Private Island (Waldorf Astoria)

• Sleeps: Up to 24 guests across 9 villas
• Highlights: Arrive by private yacht or seaplane, enjoy world-class dining, a stunning spa, and endless water activities. This is barefoot luxury at its most polished, ideal for groups who want it all in one place.

Naladhu Private Island

• Sleeps: Up to 50 guests in 20 villas
• Highlights: Each villa has its own infinity pool and butler service. The no-menu dining concept means meals are tailored exactly to your tastes. A superb option for larger groups that value privacy, flexibility, and personalised service.

Cheval Blanc Randheli Private Island

• Sleeps: 8 guests in 4 villas
• Highlights: The most intimate of the options, with ultra-refined design and dedicated ‘Ambassadeur’ service. Perfect for smaller gatherings seeking sophistication and unmatched service.

Udadoo Maldives Private Island

• Sleeps: Up to 34 guests across 15 villas
• Highlights: A solar-powered island blending sustainability with style. Ideal for eco-conscious groups who don’t want to compromise on comfort or luxury.

Four Seasons Private Island at Voavah

• Sleeps: Up to 22 guests in 7 villas
• Highlights: Arrive by private seaplane and enjoy exclusive use of Four Seasons’ world-class facilities at neighbouring Landaa Giraavaru. Exceptional service with plenty of options for relaxation and adventure.

Here Baa Atoll: Somewhere & Nowhere

• Sleeps: Up to 43 guests across 9 villas over two private islands
• Highlights: Two brand-new exclusive islands with a modern, minimalist design. A great choice for groups who want something completely fresh, contemporary, and ultra-private.

Coco Privé Private Island

• Sleeps: 12 guests
• Highlights: Full flexibility, dedicated staff, spa, gym, and pool — perfect for ultra-private small groups.

Looking for something smaller…?

Browse some of my favourite islands ideal for families and groups but booked on a non- exclusive basis

Trincomalee Beach offers a range of attractions and activities for visitors to enjoy

Sri Lanka: Culture, Coast & Complete Privacy

If your group prefers a touch of culture alongside golden beaches, Sri Lanka offers private retreats where days can be spent wandering markets, exploring temples, or just lazing by the pool with the sound of the ocean in the background. Or even do a multi stop tour here, everyone picking their own highlights, coming together at the end on the coast.

Haritha Villas, Hikkaduwa

• Sleeps: Up to 25 guests in 9 villas
• Highlights: A boutique estate combining luxury with authentic Ayurveda wellness. Close to golden beaches and Galle’s cultural heritage, this is ideal for groups wanting a mix of relaxation and local experiences.

ANI Villas, Tangalle 

• Sleeps: Up to 30 guests across 15 suites
• Highlights: Designed with large groups in mind, this resort delivers seamless five-star service. Perfect for multi-generational families or friends looking to reconnect by the ocean, with plenty of space and activities to keep everyone happy.

The Six, near Weligama

• Sleeps:  Multiple 4-bed villas, can book full estate for privacy
• Highlights: Ultra-luxury villas along Dammala Beach, each with private pool, chef, butler, and sauna — ideal for a secluded, personalised group retreat.

Let Me Take Care of the Details

Every group is different –  from multi-generational families with toddlers and grandparents to groups of friends celebrating a milestone birthday. My job is to take the stress off your shoulders: matching you with the right property, checking availability, sorting logistics, and making sure the trip runs smoothly from start to finish. We can even take care of flights too.

So, if you’re the magic- maker in your family, let me help you. Together we’ll plan a private island or resort escape that everyone in your group will remember for years to come.

Email Carly 

Written by Carly Watling

Top Travel Tip

“Both Sri Lanka and the Maldives are amazing standalone – but a combination of the two is an addictive pairing. 10 days exploring the highlights of Sri Lanka hits culture, wildlife, breathtaking scenery and incredible food at a good pace, and then you can wind down with a few nights of luxury on the most perfect beaches in the world” – Carly, Asia Specialist