Family-friendly holiday rentals in Kailua

*Serendipity on the Moana! - Legal & Beachfront!*

Gorgeous, Fully Furnished, Beachfront one-bedroom condo with over 740 square feet in Maile on Oahu. Maili Cove is a hidden gem and has easy access to golf courses, amusement parks, restaurants, shopping centers, financial and medical facilities and other services located on the west side of the island. Just 15 minutes down the road is the Disney Resort & Ko Olina. *This is a LEGAL vacation rental, so no stress! 90/TVU-0073 Owner a licensed real estate agent. Hawaii tax ID TA-147-153-1008-01

Hale He'e' Nalu (Surf House) in Turtle Bay!

Enjoy beautiful North Shore paradise at Hale He'e' Nalu (Surf House), our lovely Hawaii beach cottage with views and security. Island style living! Full kitchen, swimming pools, BBQ areas, beach gear/toys, pristine beaches, epic surfing, breathtaking hiking, PGA golf, beach horseback riding, tennis/pickle, famous restaurants! Ideally in the most desirable location at private Turtle Bay condos in Kuilima Estates West secure gated community. Fast private internet WiFi. FREE parking. No resort fee!

Honu Kai Condo Best Location at Turtle Bay

Honu Kai Condo is approximately a 7 min walk to world famous ocean views, beautiful beaches and Turtle Bay Resort. Offering two world class golf course (A. Palmer & G. Fazio), surfing, snorkeling, ocean activities, tennis courts, pools, running, mt. biking, horse back riding, casual to fine dining and fun nightlife. It's also a 10-15 min drive to the world famous beaches of the North Shore- Sunset Beach, Pipeline, Waimea Bay, Haleiwa and many more. This condo is great for couples and families.

Ko Olina Beach Villas Largest 3br/3ba w/2 Masters

Next Available: May 17 & Aug 1. Direct homeowner rental, no affiliation with Vacasa. Welcome to the largest villa at the Beach Villas at Ko Olina, a luxurious beachy retreat with a Four Seasons and Ritz-Carlton vibe. Our 3-bedroom, 3-bathroom home features two master suites and a children's bedroom, all with their own bathrooms. With beds for eight, it is an ideal home base for multigenerational families, friends traveling together, or guests seeking extra space and luxury.

Amazing Condo with Spectacular View & free parking

POOL CLOSED FROM APRIL 7TH UNTIL 2026. This amazing unit at Waikiki Banyan features a Spectacular Ocean and Diamond Head view. Just 5-minute walk (100 yards) from Waikiki Beach. Ideal for romantic vacations and family trips. Fully equipped kitchen. Beach equipment and beach towels were provided. Easy self-check-in and free parking on the premises. Sleeps 4: 2 Full-size beds, 1 Full-size sofa bed. Baby crib and booster chair provided. Cafes and restaurants within 5 min walk.

Charming home by the pool near the beac

Comfortable 1 bedroom with a loft, is nestled between pristine beaches and beautiful mountains. Located between the Fazio Golf Course at the Turtle Bay Resort! Short walk to the beach, and family-friendly activities. Pool only steps away Gated entry to the Kuilima Estates West and on site security guards. Comes with one assigned parking stall. You’ll love our place because of the coziness and the location. Great for couples, adventurers, business travelers, and families.

Dreamy Beachfront Cottage with Breathtaking Views

Looking for a beautiful, peaceful, beachfront place to stay? This is the place! Enjoy life on a tropical, sandy beach. This cottage has lovely ocean views, a large, covered patio facing the ocean, a newly remodeled galley-style kitchen, and it's furnished with everything you'll need for a great vacation. See giant, green-sea turtles sleep on this beach before heading back out to sea at dawn. Rates reduced due to construction noise nearby on weekdays.

Ocean View Owners Unit in Wyndham 4 Star Resort

Gracious and intimate best describes this distinctive property. From the moment you set foot on the rich Italian marble lobby, you are embraced with abounding elegance. The attention to detail in this perfectly located Pacific paradise leaves little to be desired. For your comfort and enjoyment, the condo has a California King Bed and a 65" wall-mounted Smart TV. Managed by BrooksBeachVacations

Modern Mango Beach Home North Shore - 30 day stays

Enjoy your Hawaii vacation in a modern "Dwell" style home. Our 2-bed 1-bath guest unit sleeps up to 6. Full kitchen, all high-end appliances. The sandy beach with crystal-clear waters is just three houses away. This home can only be rented for periods of 30 days or longer. No breakdown in pricing or calendar settings in Airbnb shall suggest that this home can be rented for a shorter period.