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Luxury beachfront rental

Kailua, Oahu, Hawaii

Paradise Point Estates is a 5-bedroom, 5.5 bathroom estate.  Located directly on Kailua Beach (consistently rated one of the best beaches in the world), simply step from the soft grass backyard to the white sand! Paradise Point Estates is a rare jewel that comes fully appointed with plantation-style finishes and furnishings from around the world. Step from a secure entry and motor court into beachfront luxury that whispers old Hawaii yet offers all of the latest amenities and technologies of a modern masterpiece.

The center courtyard of the estate features a secluded, heated lagoon-style pool and pool-pavilion including tropical waterfalls and a lavish island spa/hot tub.  The ocean lanai and garden lanai showcase ornate landscaping and stunning views.  Expansive living quarters command attention amid the artisan touch of etched windows, stained glass, natural stone tiling, and African mahogany carvings.

The kitchen has everything needed to either prepare meals on your own or to have your own (or one of our) private chef(s) create lavish meals.  Famous local chefs (Chefs Mavro and Roy Yamaguchi) and international chefs (including Chef Morimoto) have prepared meals in our kitchen for our guests.

  • Beachfront
  • 5 Bedrooms with King Beds & En Suites
  • 5.5 Baths
  • Single-Level
  • All Wheelchair Accessible
  • Heated Lagoon-Style Pool
  • Hot Tub Spa with Waterfall
  • Fitness Center with Top-of-the-Line LifeFitness Equipment
  • Gourmet Kitchen
  • Media Room
  • Celebrity-Level Security
  • Concierge
Beachfront Hawaiian Vacation Rental
Beachfront property rental Kailua
Paradise Point Estates Gated Entry
Obama Signing 9-11 First Responders Bill into Law at Paradise Point Estates


A home fit for a President

President Obama stayed in this luxury beachfront rental for the holidays and the media named it the Obama Winter White House.

Darting in and out, a young boy plays in the waves on Hawaii’s Kailua Beach. He may know that Hawaiians fished its local waters for centuries. He may even know that the shoreline was once a gathering place for Hawaiian royalty. What he does not know is that he will someday return to this exact spot as President of the United States.

Born in Honolulu in 1961, Barack Obama is Hawaii’s most famous local. After living in Indonesia for a number of years, Obama eventually returned to Oahu to live with his maternal grandparents, and later with his mother. As a ten-year-old 5th grader, the future President attended Honolulu’s Punahou School, only 20 minutes from Kailua Town. Young Barack and his grandfather would make the short trip to Kailua Beach to swim in the cool shadow of Mount Olomana. So it is no wonder that in December and January 2008-2011, the President and his family selected Paradise Point at Kailua Bay in Oahu as their holiday vacation home and the site of the Obama Winter White House.


Pictured | President Obama signing a 9/11 First Responders Bill into law in the courtyard lanai of the estate.


Add-on services

Our Concierge can help you add-on any services including, but not limited to, the following.














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    Requested Arrival & Departure Dates

    One hundred percent (100%) of the gross proceeds generated from this rental shall be distributed directly to nonprofit corporations or associations without offset or deduction by Owner.  Owner shall not receive any compensation, including any monetary payments, services, or labor, in connection with this rental.  Notwithstanding the foregoing, neither Owner nor the renter shall claim a charitable deduction in connection with the rental proceeds distributed to nonprofit corporations or associations.



    Kailua, Oahu, Hawaii



    Paradise Point Estates, LLC
    Joe Weinberg, Manager
    410-916-1429 M

    Paradise Point Estates Location Map