Barack Obama’s Vacation Estate in Kailua Bay, HI (For Rent at $4,500/Night)

This is a look at the back of the house with a lagoon-style pool surrounded by thick shrubs, tall trees and decorative mosaic stone walkways that are all complemented by the glow of the pool and the outdoor lights. Image courtesy of

President Barack Obama and his family spent their Christmas vacations in Paradise Point Estate in Hawaii from 2008 to 2011. This estate can be rented for $4,500/night.

The plantation estate in Kailua Bay is measured at 6,000 square feet with five bedrooms, six bathrooms, an open-air-style design, a gourmet kitchen, stained-glass windows, and lots of mahogany. The house also boasts of a lagoon-style pool, several waterfalls and lanais, native Hawaiian plants and coconut trees, an outside wet bar, and a seven-foot lava wall.

The plantation estate of Paradise Point that the Obamas rented every Christmas from 2008 to 2011 can be rented for $4,500/night. For more details, contact the manager of Paradise Point, Glenn Weinberg.

All photos are used with permission from

December 2016 was the last Hawaii Christmas vacation for President Obama before he transitions to life as a private citizen. Since 2008, the President and his family’s location of choice have been the once sleepy area of Kailua Bay on the windward side of the island. From 2008 to 2011, the home they rented was Plantation Estate at Paradise Point, located on a jut of land at the far end of the long crescent of Kailua beach.

The land where Plantation Estate at Paradise Point stands was once favored by Hawaiian royalty for its views and natural beauty, later purchased by missionary Samuel Castle. The property stayed in the Castle family for generations and as late as the 1960s still was guarded by the family’s Great Danes that would very effectively keep gawkers off the property. Today, it is one of the most luxurious beach resort locations in the world. Over the 2016 holiday season, the Kailua area was once again host to the Obama family and their entourage of Secret Service agents.

These Kailua Bay open-air-style estate homes on dead-end roads with few other homes include the 6,000-square-foot Plantation Estate home with a lagoon-style pool, several waterfalls, and lanais, native Hawaiian plants and coconut trees, and an outside wet bar – all behind a seven-foot lava wall. Inside the master home are five bedrooms and six baths, a gourmet kitchen, a 60-inch flat-screen TV, stained-glass windows, and lots of mahogany. Paradise Point is a perfect location for the most elegant, tropical homes on Oahu with views to Kailua Beach and the Mokulua Islands.

The President has been spending a lot of time on various golf courses around the island with his golfing buddies while the family has enjoyed the local beaches at Kaneohe Marine Base, Kailua, and Bellows Air Force Base. Residents and tourists have crowded around restaurants and other venues to cheer in appreciation for his eight years leading the country and his affection for the islands.

The Hawaii Plantation Estate at Paradise Point home that President Obama rented for his Christmas vacations from 2008 through 2011 is available for rent beginning at $4,500 a night.


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This is a look at the back of the house from the vantage of the poolside area. You can see here the glass walls of the house that glow warmly from the interior lights. Image courtesy of

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