Vacation of a Lifetime
Privacy, Adventure, Romance

Privacy Away From The World

Unbelievable Adventure Every Day

Romance Like You’ve Never Experienced

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1,000+ Villas

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30 Private Islands

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50 Countries

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In Partnership with WIMCO VILLAS

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Over 1,000 villas worldwide

From the Caribbean to the Mediterranean, and across the islands of the Pacific and Indian oceans, we have over 1,000 luxury villas. Cliffside villas with endless views and beachside villas to walk right into the sea. The villas range from two to over eight bedrooms, or go bigger with a compound or entire island!

Magnificent views

Part of the Waypoint process at Regatta is putting you on the right island for the activities that interest you. Anything from hiking to shopping to the perfect sunset, we consider all your interests, then place you on the island and with the villa to meet them.

An island to yourself!

Exploring the islands with a large party? How about your own island with a compound of villas? We have 30 islands around the world, including some very famous locations. Each island is equipped with all the amenities and provisions you'll need for a great adventure. Wanna make it a real surf and turf? Why not book a boat for a couple days as well!

Indoor-Outdoor Living

One of the wonderful attributes of island villas is how they open up! Walls become windows, and windows disappear. Feel the sea air flowing through all your rooms. Relax in the infinity pool on a cliffside villa or wander into the sea from a beachside villa. At night, close up the villa and let air conditioning lead you to a comfortable night’s sleep.

A brilliant end to the perfect day

Nothing is more awe-inspiring as a tropical sunset. There's no better place to witness it than from your villa's infinity pool. Watch the sky light up in all the colors of the spectrum. Maybe even see the elusive green flash. What you can guarantee is that it'll be the most romantic experience of your life. 

Versatile Living

Villas offer everything you'll need for the week. Wake up to the crisp clean air and gently rising sun. Spread out on the deck for fruit and pastries. Grill your own lunch or head into town to a local dining getaway. Hop in your car and head to one of many beaches on the island, then return to your pool for a relaxing cool-down. The main areas have enough room for grand meals (or really competitive board games).  

Breakfast is served.

Let us enhance your experience by delivering breakfast each morning! Local fresh fruit and pastries straight from the neighborhood patisserie are a great way to start the day. Make your own coffee or we can bring some local espresso. We're on hand to provide every detail for a perfect stay. 

Attention to quality

There are thousands of villas worldwide, but we've picked the ones that meet our high standards for luxury. Across the globe, we have an array of villas to meet your party size and lifestyle. Moreover, we are focused on the things you want to do, and ensure that the villas can meet those needs. 

Endless views from every room

Open the glass walls on a perfect day, close them on a bad day. Either way, you have amazing views of the sea. Our villas are designed to meet the conditions of all seasons. Encounter a rare storm, then sit back and watch from the safety and comfort of your villa, then open up the walls when the storm passes for a taste of that crisp post-storm sea air.