Family-friendly holiday rentals in Kailua

Kailua Beach Park - 1 BR Cottage

Kailua Beach was 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 a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/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 showers, sinks and plumbing fixtures April 2022!

*Remodeled Oceanfront in Waikiki - Ilikai Marina

Welcome to our oceanfront home offering stunning ocean views and Hawaiian sunsets, all within walking distance to the beach. Whether you're seeking adventure, family fun, or relaxation, this is the perfect destination while visiting Oahu. On Friday nights, enjoy spectacular fireworks right from your balcony. We look forward to sharing recommendations for local restaurants, beaches, and activities to make your time in Hawaii unforgettable. Book now and start planning your island getaway with us!

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. **Please note bookings after may 15th the sauna will be removed for renovations!

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.

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

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.

Sea Cliff House - Oceanfront - 30 Day Stays

Imagine seeing the crystal-clear waters of Laie Bay from nearly everywhere in the house. Eating breakfast out on the lanai so close to the water you feel like you're standing on the ocean. The gentle waves lulling you into a peaceful sleep while the ocean breezes envelope you. This is the Sea Cliff House. 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.

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym

Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We've got you covered with all the beach amenities you'll need to enjoy the crystal-clear waters and white sandy beaches. Whether you're looking for a romantic escape or a fun-filled family vacation, our property has everything you need to create unforgettable memories.

Turtle Bay Condo. Amazing retreat!

* North Shore * Pristine beaches * Rocky shores * Beautiful mountains * 2 PGA golf courses * Horseback riding * Surfing/kayaking/paddle board * Hiking/biking trails * Activity rentals * Restaurants/bars * Entire condo * Comfortable living space * Outdoor amenities * Gated entry * Assigned parking * On-site security guard * Three swimming pools * 2 tennis courts * 4 Pickle ball courts Suitable for couples, adventurers, business travelers, and families.

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.

Condo w/Turtle Bay, pool & beach access

Experience laid‑back North Shore living just steps from Turtle Bay, with resort‑style amenities, a private patio, and easy beach access. - Sleeps 4 | 1 bedroom + loft | 3 beds | 2 baths - Shared pool year‑round, tennis & pickleball courts - Beach access, beach essentials & kayak - Private patio/balcony w/ BBQ grill - Kitchen, Wi‑Fi, workspace & in‑unit washer/dryer - Family‑friendly w/ Pack ’n play, toys & board games

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.