Vacation rentals in Kailua
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Kailua
Guests agree: these stays 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!
"Endless Summer" Beachfront Condo w/ Full Kitchen!
Welcome to the beach! Your little piece of paradise! This 1 large bedroom has a new king bed, and there is a bed in the living room as well. Right on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped remodeled kitchen, washer/dryer & private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!
SEArider TWO at Turtle Bay (1 bedroom / 1 bath)
Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)
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.
Nai’a Suite at La Bella’s-Walk to Beach-Licensed
La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.
Floor-to-Ceiling Oceanfront Home (Car Available)
* Aloha! Welcome to the happiest place in the world. * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. This beachfront home is within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Every time I come to Hawaii, I am so happy. I hope our place can bring you some happiness too. :-)
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.
Kailua Rental for Med/Long Term ($1,500/month)
Escape to beautiful Kailua and enjoy our cozy guest suite! Located in a quiet cul-de-sac, this unit provides modern amenities, a new full-sized bed and direct access to your own private lanai. Mountain views, nearby attractions, shopping, dining, and world-class beaches ensure an ideal destination for your next retreat! We welcome minimum stays of 30 days or more. Please contact for inquiry details. * 30 night minimum
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.
Kailua Beach Cottage - 1990/NUC-1797
WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.
Let's make a dream
The Makaha Dream is a gated beachfront condo (Hawaiian Princess) on the fabulous Turtle beach, directly next to Mount Lahilahi. Listen to the melodic sound of waves hitting the shore, watch seals and turtles from your own balcony. Relax and enjoy the west side, away from the hustle and bustle of the city. Experience Hawaiian sunsets lighting up the evening skies, it doesn’t get any better than this!
Ocean View Beach Condo with private lanai
The only on-the-beach oceanfront condominium building in Waikiki! This spacious studio features a private lanai with stunning ocean and mountains view. Ocean breeze and breathtaking sunsets are guaranteed! King size bed, split AC, fully equipped kitchen, beach gear, and unbeatable walking distance to top Waikiki attractions, shops, and restaurants. Your perfect beachfront getaway awaits! STR#294
Popular amenities for Kailua vacation rentals
Stay near Kailua's top sights
Kailua beach vacation rentals
*Remodeled Oceanfront in Waikiki - Ilikai Marina
Waikiki Shore - Beachfront
Beach Beauty and Comfort in remote Oahu Paradise
Beachfront! Upgraded modern w Oceanview (WS1116)
Ocean View w/ 2 private balconies; Steps to Beach
*Serendipity on the Moana! - Legal & Beachfront!*
Ocean/Fireworks View Waikiki Walk to beach 1BR
9K Hawaiian Princess - Alii Hale Aina
Kailua home rentals
Haleiwa Waterfront House
Large family home 5 min from beach- with pool
Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai
North shore Studio with sauna! - Walk to beach!
Golf Course Front Condo in Kahuku
Large Kailua Beach Home - Steps To The Beach!
Family Ocean Oasis, Hot Tub, 5 min drive to beach
Slice of Paradise-3BR- Sleeps10-Max 8 Adults
Beach home rentals in Kailua
Orchid Paradise- AC, Close to beach
Sweetheart Sale! Turtle Bay’s Kuilima West #104
Kaia Villa at Turtle Bay/North Shore Oahu
Waikiki Close To Ala Moana, Pool and Parking!
North Shore Beach House! Best Location
Honolulu Oasis for your Hawaiian retreat
"HALE HONU" North Shore Beach House
Serenity Beachfront Cottage- NUC No 90/TVU-0326
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ914 | ﺩ.ﺇ918 | ﺩ.ﺇ826 | ﺩ.ﺇ826 | ﺩ.ﺇ870 | ﺩ.ﺇ870 | ﺩ.ﺇ870 | ﺩ.ﺇ845 | ﺩ.ﺇ786 | ﺩ.ﺇ841 | ﺩ.ﺇ823 | ﺩ.ﺇ848 |
| Avg. temp | 22°C | 22°C | 23°C | 24°C | 24°C | 26°C | 26°C | 27°C | 26°C | 26°C | 24°C | 23°C |
Frequently Asked Questions
What are the best places to stay in Kailua?
Stays in central Kailua let you explore vibrant shops and restaurants, while accommodations near Lanikai offer relaxed beach access. Both areas are frequently suggested for those looking for a local experience.
What are the best things to do in Kailua with kids?
Kailua Beach Park has gentle waves for swimming, and the Kalapawai Market is known for casual snacks and treats. Kayaking on the bay and exploring nearby nature trails are also frequently suggested for families.
What are some of the best things to do in Kailua?
Explore kayaking or paddleboarding in the calm bay, hike up to the Lanikai Pillboxes, and unwind at Kailua Beach Park. Kailua’s farmers' markets, local eateries, and bike paths are also frequently suggested.
How is the weather in Kailua?
Kailua has warm temperatures throughout the year, ranging from about 65–85°F (18–30°C). Rain is more frequent in winter and early spring, while summers are sunnier with less rainfall.
When is the best time to visit Kailua?
May through September has warmer temperatures around 70–85°F (21–30°C) and less rainfall, making it a popular time for beach outings. Late spring and early fall are often enjoyed for smaller crowds and local festivals.
What are the best places to visit in Kailua?
Frequently suggested spots in Kailua include the white sands of Kailua Beach Park, the scenic Lanikai Beach, and the Pillbox Hike for panoramic coastal views. The neighborhood also has inviting local markets and art galleries.
What are some hiking trails in Kailua?
The Lanikai Pillbox Hike is frequently suggested for its scenic coastal views and moderate climb. Locals also explore forested paths in nearby natural reserves, where you can experience native plants and ocean breezes.
What are some family activities we can do in Kailua?
Families can explore calm swimming beaches, rent bikes for easy paths, or visit local playgrounds in Kailua. Kayaking, visiting markets, or observing wildlife at Kawainui Marsh are also popular choices among visitors with children.
What are some of the best day trip ideas from Kailua?
Day trips around Kailua can include exploring lush botanical gardens, visiting the North Shore’s surf spots, or hiking in forested preserves. The area also has popular historic sites and cultural centers within easy reach.
Are there any pet friendly accommodations available in Kailua?
Many accommodations in Kailua are pet friendly, especially around central neighborhoods and residential areas. Parks and outdoor cafes make it convenient for guests traveling with pets.
What are some local tips for visiting Kailua?
Weekdays generally feel quieter at popular beaches, and early mornings are good for catching sunrise views from Lanikai. Remember to respect local customs, pack out what you bring, and use reef-safe sunscreen to protect marine life.
What is Kailua known for?
Kailua is known for its wide, sandy beaches, calm turquoise waters, and relaxed community vibe. The area has scenic hiking, local food spots, and opportunities to experience traditional Hawaiian culture.
What are the best hidden gems to explore in Kailua?
Kailua has quiet local beaches, shaded marsh trails for birdwatching, and small independent shops where you can explore local crafts. Consider wandering untouristed sections of Kailua Beach or the nearby Kawainui Marsh trail for a more laid-back experience.
What are the best foods to try in Kailua?
Kailua has fresh poke bowls, local plate lunches, and tropical fruit smoothies that are often recommended. Shave ice and pastries from neighborhood bakeries add to the area’s favorite flavors.
What should I bring for a trip to Kailua?
Pack light, breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for comfort in Kailua's warm weather. If you plan to hike or explore nature, closed-toe shoes and a reusable water bottle are often recommended.
What is the nightlife in Kailua like?
Kailua has a relaxed nightlife scene with welcoming bars, laid-back dining spots, and venues that occasionally feature live music. Most nightlife is concentrated in town, and evenings often center around enjoying local flavors in a casual atmosphere.
What are the most popular events or festivals in Kailua?
Kailua frequently hosts street fairs, annual parade celebrations around holidays, and open-air art markets. Late spring and holiday weekends are often filled with local music, food, and craft events.
Are there family friendly vacation rentals in Kailua?
Kailua has many family-friendly rentals, often located near beaches or local parks. These options typically include amenities like kitchens, outdoor space, and easy access to nearby attractions.
All about Kailua
With stretches of powdery white sand beaches, two reef-protected lagoons, and temperatures kept on the comfortable side of cool by ever-present trade winds, it’s no surprise Kailua is no longer the secret destination guarded by seasoned island vacationers that it once was. Located on the windward side of Oahu on a peninsula overlooking the crescent-shaped Kailua Bay and the Koolau Mountain range, Kailua is beloved for its small beach town vibe — a mellow yin to Honolulu’s metropolitan yang, with only a 25-minute drive separating the destinations.
There’s also an increasing possibility of rubbing well-tanned shoulders with vacationing celebrities drawn to the same soft sand beaches and tranquil aquamarine waters delivering on the promise of paradise. In Kailua you can revel in a variety of water sports. Hikers have a range of challenging trails to choose from, some leading to breathtaking mountaintop views, others to such secluded mountain-fed pools as Maunawili Falls, along with a network of leisurely footpaths awaiting within the 830 acres of Kawainui Marsh.
What are the top things to do in Kailua?
Lanikai Beach
Lanikai Beach is often described as one of the world’s greatest beaches, and it’s easy to see why, with its breathtaking stretches of sand and ocean overlooking two nearby islets, the Na Mokulua. The waters here are typically calm, with a protected coastline buffered from windpowered waves thanks to a sizable reef offshore, making it one of the more swimmable spots on Oahu. These placid coastal waters are hard to beat — especially for kayaking and paddleboarding — tempting the more adventurous to paddle around those two offshore islands colloquially referred to as the Mokes.
Kawainui Marsh
Binoculars and a camera are a must while visiting Kawainui Marsh, the state’s largest protected wetlands, a sanctuary where many of Oʻahu’s endemic, endangered, and migratory birds, fish, and other aquatic life can be observed in their natural habitat. Travel by foot or by bike along a paved three-mile round path in a watershed that fed ancient Hawaiians with its abundance.
BookEnds
If you identify as a bibliophile and/or a lover of Hawaiian history, you might lose yourself once entering the door of this small neighborhood bookstore. BookEnds is filled with an extensive collection of Hawaiiana reflecting the islands’ history through photography, arts and crafts, architecture, and music.
Quick stats about vacation rentals in Kailua
Total vacation rentals
Explore 340 vacation rentals in Kailua
Nightly prices starting at
Kailua vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees
Verified guest reviews
Over 11,150 verified reviews to help you choose
Family-friendly vacation rentals
190 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 40 rentals that welcome pets
Vacation rentals with a pool
90 properties feature pools
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wi-Fi availability
330 of Kailua vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Beachfront, and Gym across Kailua rentals
4.9 Average rating
Kailua stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Honolulu Vacation rentals
- Oahu Vacation rentals
- Kauai Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikīkī Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kona Vacation rentals
- Kihei Vacation rentals
- Kaanapali Vacation rentals
- North Kona Vacation rentals
- Princeville Vacation rentals
- Hilo Vacation rentals
- House rentals Kailua
- Pet-friendly rentals Kailua
- Guesthouse rentals Kailua
- Rentals with a washer and dryer Kailua
- Private suite rentals Kailua
- Rentals with a kayak Kailua
- Beachfront rentals Kailua
- Villa rentals Kailua
- Beach condo rentals Kailua
- Rentals with a hot tub Kailua
- Rentals with pools Kailua
- Rentals with an EV charger Kailua
- Apartment rentals Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Rentals with outdoor seating Kailua
- Rentals with beach access Kailua
- Family-friendly rentals Kailua
- Rentals with a patio Kailua
- Condo rentals Kailua
- Waikiki Beach
- Kailua Beach
- Kualoa Ranch
- Waimea Bay Beach
- Lanikai Beach
- Ala Moana Beach Park
- Kepuhi Beach
- Banzai Pipeline
- Honolulu Zoo
- Kapiolani Park Beach
- Mākua Beach
- Hanauma Bay Nature Preserve
- Bishop Museum
- Waimea Valley
- Wet 'n' Wild Hawaii
- Kailua Beach Park
- University of Hawaiʻi at Mānoa
- Lanikai Pillbox Hike
- Waimea Bay Beach
- Pyramid Rock Beach
- Kalama Beach Park
- Dole Plantation
- Iolani Palace
- Ko Olina Golf Club
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Tours Honolulu County
- Nature and outdoors Honolulu County
- Entertainment Honolulu County
- Sightseeing Honolulu County
- Art and culture Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Tours Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Art and culture Hawaii
- Food and drink Hawaii
- Entertainment Hawaii
- Things to do United States
- Tours United States
- Food and drink United States
- Entertainment United States
- Sightseeing United States
- Wellness United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States