
Family-friendly vacation rentals in Kailua
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Kailua
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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!

Secluded White Sandy beach just 30 steps away
Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits

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.

Kailua Pineapple Studio. Walk to Beach! PERMITTED
Legal, permitted short-term rental (Permit #1990/NUC-1819, Tax map key:43073024) *not impacted by Honolulu ordinances banning Short-term Rentals Hawaiian style, modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Managed by Kupono Svcs.

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.

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!

Beach Beauty and Comfort in remote Oahu Paradise
This is among the nicest locations in all Hawaii. You are literally over a quiet, beautiful pristine beach. Beautiful valley views East. Sparsely populated beach below. Excellent sand and swimming. Beach amenities on hand. The condo is beautiful, comfortable, and nicely updated. Great local swimming, snorkeling, surfing, hiking, dolphins, turtles. Personally, I do not know a better place in Hawaii to visit if you do not need bars and shopping. Nice facility amenities below.

Studio at Marriott vacation club ko olina
Feel free to message me a request to book and the times you are looking for. The price shown is for the Mountain View Studio w/kitchenette that sleeps 4, 1 King and a Sofa Bed. Price is over half of the cost if you book direct with the hotel. Also includes FREE parking where hotel charges $45/day. The most beautiful resort and Guest room in Ko Olina right on the beach in a picturesque lagoon. 30 minutes from the airport and Honolulu. * Free WiFi, Free self-parking.

"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.

♥ 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, 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!

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.
Popular amenities for Kailua family-friendly rentals
Family-friendly home rentals with a hot tub

High FL-Upscale Ocean View w/ Easy Beach Access~

Waikiki Gem, Stunning Ocean View, Parking Included

Ko Olina Beach Villa | Beach View | Free Parking

2BR High Floor Free Parking

Amazing Central Waikiki Wonder

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

North Shore Oahu | Turtle Bay - Hale Kahakai

Elegant, Spacious Downtown Hideaway w/Parking
Family- and pet-friendly home rentals

Aloha Living Near Ko’olina + WiFi/Sleeps 4

Newly Renovated * Waikiki Beachside Retreat

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

DIAMOND ON DIAMOND HEAD

Explore | Waikiki Walkable Escape~Surf, Hike, Dine

Aloha Surf Condo - Private Deck - Pool - E-Bikes

Spectacular Oceanview Cottage

Waikiki studio with balcony block from the beach
Family-friendly home rentals with a pool

Villa 302, King bed, Penthouse Lvl Ocean View Turt

★Panoramic OCEAN VIEW Studio Suite + FREE Parking

Hawaiian sunrise retreat

North Shore Getaway - Newly renovated!

Chic Private Guest House • Pool • Gym • Hikes

Stunning Ocean views of Honolulu

North Shore Oahu Getaway at Turtle Bay Resort

Waikiki Ocean & Sunset View Condo-free parking
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $375 | $475 | $375 | $375 | $400 | $395 | $353 | $450 | $412 | $375 | $400 | $393 |
| Avg. temp | 72°F | 72°F | 73°F | 74°F | 76°F | 78°F | 79°F | 80°F | 80°F | 78°F | 76°F | 73°F |
Quick stats about vacation rentals that are family-friendly in Kailua

Total vacation rentals
Explore 190 vacation rentals in Kailua

Nightly prices starting at
Kailua vacation rentals start at $100 per night before taxes and fees

Verified guest reviews
Over 3,280 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
190 of Kailua vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kailua rentals

4.9 Average rating
Kailua stays are highly rated by guests—averaging 4.9 out of 5!
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- Waikiki Beach
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- Kualoa Ranch
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- Ala Moana Beach Park
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- Ko Olina Golf Club
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