Family-friendly holiday rentals in Kailua

Kailua Beach Park - 2 BR Cottage

Kailua Beach is once again been rated as the best beach in the USA for 2019, by Dr. Beach. "The cottage is directly across the street from Kailua Beach Park and less than two minutes walk to step into the ocean at the beach. This a legal vacation rental, license1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new shower, sink and plumbing fixtures April 2022!

Honu Suite at La Bella’s-Walk to Beach-Licensed

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.

Ocean View w/ 2 private balconies; Steps to Beach

BEST LOCATION & OCEAN VIEWS! Steps to Waikiki Beach & all the action! No car needed Newly renovated condo 1/2 block to the beach on 9th floor of Waikiki Grand Hotel. Across from the Zoo in Kapiʻolani Park. Enjoy 2 private balconieswith Ocean/Diamond Head views. 1 Queen bed & 1 Queen Pull Out. Dividers provided to convert into 1 bedroom if needed. See photos of Full Kitchenette & beach gear included LEGAL VACATION RENTAL All taxes/fees included—your family or solo dream vacation starts here!

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo nestled in the dreamy North Shore of O‘ahu. Our home is located in the gated community of Kuilima Estates West, within the renowned Turtle Bay Resort. You'll be just a 5–10 minute walk from breathtaking shorelines, world-class surf spots, romantic dining experiences, and endless adventures by land and sea. Kuilima Estates is also the only area on the North Shore where vacation rentals are legally permitted—offering you a unique and worry-free island escape.

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

NEWLY RENOVATED (2021) Turtle Bay Haven!

NEWLY RENOVATED condo (2021) at Turtle Bay on Oahu's world famous North Shore. Enjoy more than 5 miles of secluded beaches, 2 private swimming pools, 2 private tennis & pickle ball courts, 2 PGA golf courses, horseback riding & fine dining all less than a 5 minute walk from your front door! The condo was completely remodeled in 2021 (Kitchen, Bathrooms, Flooring, decor as well as AC throughout). This 1Bed, 2Bath unit is one of the few Legal and licensed vacation rentals on the North Shore!

3BR, Near Beach, Game RM, Private Spa, Pool, Gym

Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

"Coconut Cottage by the Sea" Steps to the beach!

Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym, security & FREE parking!

♥ North Shore Paradise at Turtle Bay ♥

For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.

North shore Studio with sauna! - Walk to beach!

Legal Nightly Vacation Rental (No 30-day contracts) A cozy, island-style unit with a loft bed, perfect for an authentic Hawaiian getaway. The unit includes High speed WiFi, 65 inch Smart TV, Split unit AC, sauna, an outdoor shower, an outdoor gym, a sun deck, and private access. Located within walking distance to famous Waimea Bay and other beautiful spots, this space offers convenience, comfort, and island charm. Check my profile for other rentals!

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.