
Vacation rentals in Kailua
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Top-rated vacation rentals in Kailua
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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

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.

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks
Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

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.

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.

♥ 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.

Waikiki Beachfront Home with Ocean and Beach View
* Aloha! Welcome to our happy place in the heart of Waikiki! * If you are looking for stunning ocean views directly from your bed, this is it! You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Our spacious bedroom, full kitchen, and freshly updated bathroom will make you feel just like home. Welcome to our little paradise!

[Rare] Premier Ocean and Diamond Head Views 33 FL
The Honu Suite is a serene, design-forward retreat in the heart of Waikiki - just one block from the beach. Enjoy panoramic Diamond Head and ocean views from the 33rd floor, curated amenities, and five-star touches throughout. Rooted in Hawaiian heritage, it's perfect for discerning couples seeking comfort, style, and a sense of escape. Limited-time: Complimentary early check-in and late check-out, based on availability.

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.

Aloha Hidden Treasure
This is the slice of Paradise. This unique ocean front condo located at the four floor, is steps away from a pristine Hawaiian soft-sand beach. Sit & enjoy the ocean. Take it easy at this unique getaway. The price has a big discount, because building is under construction, can be noisy between 8 to 4, M to F. Better be out to enjoy the beach and the island. TMK#530080020054 TA-075-900-3648-01
Popular amenities for Kailua vacation rentals
Kailua beach vacation rentals

★Panoramic OCEAN VIEW Studio Suite + FREE Parking

Beach Beauty and Comfort in remote Oahu Paradise

*Serendipity on the Moana! - Legal & Beachfront!*

Dreamy Beachfront Cottage with Breathtaking Views

Ocean views at Ilikai Marina - Parking included!

Makaha Dream

9K Hawaiian Princess - Alii Hale Aina

Aloha Beach Front Cottage
Kailua house rentals

Haleiwa Waterfront House

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Nalu's Island Home

Hula Hideout ~ Airbnb’s Favorite Home - Top 1%

Beautiful 4-BR Home| Near Beach| Mountain View

Hawaiian Country Retreat - 30 day stays

3BR New Construction w/Mt views, Close to Beach
Beach house rentals in Kailua

Orchid Paradise- AC, Close to beach

Kamalani's Hale, beachfront- 30 day minimum stay

Beautiful Ocean view 2 bedroom rental (30 + days)

Kaia Villa at Turtle Bay/North Shore Oahu

Oceanfront Escape Your Hawaii Home Away from Home

"Hina Hideaway", Views, AC, Walkable to Beach

A/C Surfer family home 3 minutes walk to the beach

"HALE HONU" North Shore Beach House
Quick stats about vacation rentals in Kailua
Total rentals
340 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
90 properties have a pool
Your guide to Kailua
Welcome to 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.
The best time to stay in a vacation rental in Kailua
With an average temperature of 81 degrees Fahrenheit, there’s really no bad time to stay in one of Kailua’s vacation rentals. Months spanning from spring through fall generally offer the best balance between agreeable (dry) days, with sparser crowds that spike after Thanksgiving. Kailua’s windward location on the island means sweltering heat will rarely be a concern here, and the weather is almost always pleasant. Mornings can be a little muggy, though, before the trade winds flush out the humidity, perpetually moving clouds overhead to reveal the shockingly blue skies. If you plan to travel from November through early spring, come prepared for rainfall, including footwear outfitted for muddy conditions.
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.
Frequently Asked Questions
How is the weather in Kailua?
Kailua's weather remains warm throughout the year with an average temperature ranging from 70°F (21°C) to 85°F (29°C). It sees the most rain from November to March, while the driest months are June to September.
What are some of the best things to do in Kailua?
Popular activities in Kailua include swimming, kayaking, or windsurfing at Kailua Beach, hiking the scenic trails such as the Olomana Trail, and exploring local markets like the Kailua Farmers Market. Visitors also enjoy sampling local cuisine at the many eateries in town.
What is the best time of year to visit Kailua?
Kailua is mostly visited during the summer months, particularly from May to September. Around this time, visitors can enjoy events such as the Kailua Independence Day Parade in July. The period between December and April is also popular, especially for those looking to escape colder weather.
What are the best places to stay in Kailua?
Visitors to Kailua often prefer staying in places close to its natural beauty. Lanikai, known for its beach, and Enchanted Lake, a residential area with a shopping center, are popular choices. Notably, Maunawili, with its proximity to hiking trails, also attracts nature lovers.
What are the best places to visit in Kailua?
In Kailua, Lanikai Beach and Kailua Beach Park are frequented by sun-seekers and water sports enthusiasts. Nature lovers often explore the Maunawili Falls Trail and the Kawainui Marsh. The Kailua Farmers Market is a favorite among food enthusiasts for its local produce.
What are some hiking trails in Kailua?
Kailua has several hiking trails for nature enthusiasts. The Olomana Trail, offering three peaks of varying difficulty, and the Maunawili Falls Trail, leading to a waterfall, are popular choices. The relatively easy Pillbox Hike offers great views of the town and ocean.
What are some family activities to do in Kailua?
Families in Kailua can enjoy a day at the beach, try stand-up paddleboarding, or visit Kalapawai Market for a picnic lunch. They can also explore Pillbox Hike for a fun family adventure or visit the Thursday Night Farmers Market for a taste of local food and culture.
What are some of the best day trip ideas in Kailua?
From Kailua, day trips can include exploring the marine life at Hanauma Bay, hiking the Ko'olau Mountain Range, or visiting the Byodo-In Temple in the Valley of the Temples. Trips to the bustling city of Honolulu, just 19 km away, are also enjoyed by many.
Are there vacation rentals with a dedicated workspace in Kailua?
Yes! Work meets play with ease at over 180 vacation rentals in Kailua featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Kailua?
Four-legged friends are welcome in Kailua. Choose from more than 50 vacation rentals for guests traveling with pets.
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- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- Mālaekahana Beach
- Honolulu Zoo
- Ala Moana Beach Park
- Banzai Pipeline
- Mākoa Beach
- Kalama Beach
- Hanauma Bay
- Kapiolani Park Beach
- White Plains Beach
- Sans Souci Beach
- Bishop Museum
- Kahala Hilton Beach
- Wet 'n' Wild Hawaii
- Nimitz Beach
- Diamond Head Beach Park
- Pyramid Rock Beach
- Ke Iki Beach
- Kalani Beach
- Things to do Kailua
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- Food and drink Honolulu County
- Nature and outdoors Honolulu County
- Wellness Honolulu County
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- Art and culture Honolulu County
- Things to do Hawaii
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- Tours Hawaii
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- Nature and outdoors Hawaii
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