Vacation rentals in Kailua
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Quick stats about vacation rentals in Kailua
Total vacation rentals
Explore 310 vacation rentals in Kailua
Nightly prices starting at
Kailua vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees
Verified guest reviews
Over 10,170 verified reviews to help you choose
Family-friendly vacation rentals
180 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 50 rentals that welcome pets
Vacation rentals with a pool
80 properties feature pools
Rentals with dedicated workspaces
150 properties have a dedicated workspace
Wi-Fi availability
300 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!
Top-rated vacation rentals in Kailua
Guests agree: these stays are highly rated for location, cleanliness, and more.
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!
Beautiful 4-BR Home| Near Beach| Mountain View
A tastefully designed 4 bed/2.5 bath home in a gated community (built in 2022), nestled in the beautiful Makaha Valley. Private back yard with breathtaking Wai’anae Mountain view and peek-a-boo oceanview. Enjoy quality time with your family and friends at this stylish, cozy home. Experience true taste of paradise on western side of Oahu, away from hustle and bustle of city. The endless beaches along the coastline, amazing sealife, and magnificent mountains will make your vacation memorable!
Beachfront Home (Car & Parking Available)
* Aloha! Welcome to our happy place - our beachfront home! * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. The location is right on Waikiki Beach. You are 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 happy. I hope our place can bring you happiness too. :-)
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.
Cottage Nene - Luxury Home by Beaches & Mountains
Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.
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! There’s 2 Ilikai pool iavailable for our guests. Also accepting long term stays at special rates.
Sea Cliff House 2 - Oceanfront Home - 30-day stays
Guests said: "Probably the BEST place I have ever stayed. Not a single downside." "This house is too beautiful for words." "Love love love the place!! Thank you!!" You'll love this oceanfront North Shore Oahu home, too. See the crystal-clear waters of Laie Bay from nearly everywhere in the house. Dine on the lanai with the ocean so close you feel like you can touch it. The Sea Cliff House is on beautiful Laie Point, a unique peninsula on the quiet side of Oahu.
"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.
Condo near Turtle Bay w/pool, beach & BBQ
Experience laid‑back island living on Oahu’s North Shore, just steps from Turtle Bay and the beach. Relax on the patio with sunrise coffee or unwind after surf sessions. - Sleeps 4 | 1 bd + loft | 3 beds | 2 baths - Year‑round pool, tennis & pickleball courts - Beach access, beach essentials & kayak - Private patio/balcony w/ BBQ grill - Kitchen, Wi‑Fi, workspace & in‑unit washer/dryer - Family‑friendly: Pack ’n play, toys & board games
Tropical Kailua Retreat | Walk to Beach + Gym
Walk to one of Hawaii’s most beautiful beaches, explore Kailua by kayak or bike, and relax in your own tropical retreat. The Honu (Turtle) Suite at La Bella’s Bed & Breakfast offers privacy, comfort, and island charm just minutes from the beach. Enjoy a queen bed with luxury linens, air conditioning, a full kitchen, private bathroom, private entrance, and outdoor seating area surrounded by tropical gardens on Oʻahu’s beautiful Windward Coast.
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 vacation rentals
Stay near Kailua's top sights
Kailua beachfront vacation rentals
*Remodeled Oceanfront in Waikiki - Ilikai Marina
Oceanfront Skyline Views From Bed!/Free Parking
Ko Olina Oceanfront | Disney | Next Avail 08/26
Beach Beauty and Comfort in remote Oahu Paradise
Secluded White Sandy beach just 30 steps away
*Serendipity on the Moana! - Legal & Beachfront!*
Studio Suite @ Ko Olina Marriott Vacation Club : D
Niihau Lux
Kailua home rentals
Waikiki Gem, Stunning Ocean View, Parking Included
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!
Hibiscus Hale on Gated Estate + Walk to the Beach
Makaha Hale - Serene 3 BR Home
60 second walk to Lanikai Beach. 2 Bedrooms w/ AC
Slice of Paradise-3BR- Sleeps10-Same$ for 10 as 2
Beachfront home rentals in Kailua
Orchid Paradise- AC, Close to beach
Aloha August Sale! Turtle Bay’s Kuilima West #104
Newly Renovated Villa Walk to Beach + Pool
Waikiki Close To Ala Moana, Pool and Parking!
Honolulu Oasis for your Hawaiian retreat
"HALE HONU" North Shore Beach House
Tropical Tranquility | Amazing Ocean Views, AC
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.ﺇ 812 | ﺩ.ﺇ 826 | ﺩ.ﺇ 830 | ﺩ.ﺇ 826 | ﺩ.ﺇ 870 | ﺩ.ﺇ 870 | ﺩ.ﺇ 870 | ﺩ.ﺇ 845 | ﺩ.ﺇ 786 | ﺩ.ﺇ 746 | ﺩ.ﺇ 808 | ﺩ.ﺇ 793 |
| 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.
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