Kailua vacation rentals

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Top-rated vacation rentals in Kailua

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost
Home 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!
Jun 5 – 12
$280 per night
4.85 out of 5 average rating, 340 reviews
Guest favorite
Condo in Kahuku
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.)
Dec 15 – 22
$449 per night
4.91 out of 5 average rating, 146 reviews
Guest favorite
Condo in Kahuku
Honu Hideout at Turtle Bay
Come escape to Honu Hideout on the exclusive North Shore of Oahu, and enjoy this newly renovated ground floor unit situated just a short walk away from the iconic Turtle Bay Resort and the most breathtaking and secluded beaches on Oahu. Far away from the hustle and bustle of Honolulu, this unit offers the peacefulness of the country and the proximity to infamous attractions for the vacation of your dreams. Relax and restore or adventure and explore, you choose, all within minutes of your door.
Oct 5 – 12
$415 per night
4.98 out of 5 average rating, 104 reviews

Popular amenities for Kailua vacation rentals

Stay near Kailua's top sights

Kailua Beach Park200 locals recommend
Whole Foods Market370 locals recommend
Pillbox Hike178 locals recommend
Boots & Kimo's Homestyle Kitchen51 locals recommend
Kailua Beach Adventures40 locals recommend
Buzz's Steakhouse136 locals recommend

Kailua beach vacation rentals

Superhost
Apartment in Hauula
Aloha Hidden Treasure
Apr 28 – May 5
$230 per night
4.88 out of 5 average rating, 111 reviews
Guest favorite
Condo in Kahuku
♥ North Shore Paradise at Turtle Bay ♥
Dec 9 – 16
$446 per night
4.92 out of 5 average rating, 132 reviews
Guest favorite
Apartment in Makaha
OCEANFRONT PARADISE Tennis Pool Jacuzzi A/C W/D
Jul 21 – 28
$250 per night
4.97 out of 5 average rating, 132 reviews
Superhost
Guesthouse in Haleiwa
Walk to Beach Large Studio
Oct 29 – Nov 5
$155 per night
4.78 out of 5 average rating, 247 reviews
Guest favorite
Condo in Kahuku
HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu
Nov 29 – Dec 6
$441 per night
5.0 out of 5 average rating, 118 reviews
Guest favorite
Condo in Kahuku
Turtle bay retreat
Jul 22 – 29
$221 per night
4.87 out of 5 average rating, 245 reviews
Superhost
Guest suite in Haleiwa
Hale Nalu a/c, beach, bike path, food trucks, cook
Nov 22 – 29
$260 per night
4.8 out of 5 average rating, 152 reviews
Guest favorite
Guest suite in Haleiwa
Serene Studio for 30 Days only
Jun 29 – Jul 6
$269 per night
4.96 out of 5 average rating, 248 reviews
Guest favorite
Condo in Kahuku
Modern & Contemporary North Shore Oahu Condo
Oct 7 – 14
$349 per night
4.98 out of 5 average rating, 198 reviews
Guest favorite
Condo in Kahuku
Luxe Loft at Turtle Bay
Feb 3 – 10
$414 per night
4.81 out of 5 average rating, 311 reviews
Superhost
Guesthouse in Hauula
Brand New, Beach Front, Villa Aloha 30-day min
Nov 20 – 27
$648 per night
4.88 out of 5 average rating, 131 reviews
Guest favorite
Condo in Kahuku
Turtle Bay Condo- Kuilima Estates
Oct 1 – 8
$282 per night
4.93 out of 5 average rating, 102 reviews

Kailua house rentals

Guest favorite
Home in Kaneohe
Perfect way to explore Oahu! Kaneohe 30 days
May 10 – 17
$227 per night
4.86 out of 5 average rating, 309 reviews
Guest favorite
Home in Hauula
Private Waterfront House AC & Fast Wi-Fi
Apr 1 – 8
$260 per night
4.87 out of 5 average rating, 142 reviews
Superhost
Home in Haleiwa
Haleiwa Dream Location
Jan 28 – Feb 4
$350 per night
4.83 out of 5 average rating, 227 reviews
Guest favorite
Home in Honolulu
Beautiful Two Bedrooms, Gated & Private Entrance
Nov 9 – 16
$437 per night
4.88 out of 5 average rating, 111 reviews
Guest favorite
Home in Kahuku
Hawaiian Country Retreat - 30 day stays
Aug 14 – 21
$271 per night
4.89 out of 5 average rating, 217 reviews
Superhost
Home in Hauula
Hauula Studio
Oct 2 – 9
$186 per night
4.83 out of 5 average rating, 246 reviews
Superhost
Home in Kailua
Tropical Cottage w/Pool, Lanai & AC, Walk to Beach
Feb 13 – 20
$857 per night
4.88 out of 5 average rating, 49 reviews
Guest favorite
Home in Kailua
Cute & Charming, Minutes to Town and Kailua Beach
Apr 30 – May 7
$550 per night
5.0 out of 5 average rating, 34 reviews
Superhost
Home in Kailua
Large Home in Kailua - Steps to the Beach!
Oct 16 – 23
$732 per night
4.75 out of 5 average rating, 91 reviews
Guest favorite
Home in Kaneohe
Chinaman’s Ocean Front Beach House
Jan 17 – 24
$606 per night
4.96 out of 5 average rating, 46 reviews
Guest favorite
Home in Haleiwa
Haleiwa Waterfront House
Jan 5 – 12
$890 per night
5.0 out of 5 average rating, 34 reviews
Superhost
Home in Kaaawa
Private Beachfront Oasis
May 16 – 23
$594 per night
4.9 out of 5 average rating, 20 reviews

Beach house rentals in Kailua

Superhost
Home in Haleiwa
Waimea Bay, North Shore - 2BD Walk to beach!
Dec 24 – 31
$342 per night
4.79 out of 5 average rating, 24 reviews
Guest favorite
Home in Hauula
North Shore Beach Life!
Sep 24 – Oct 1
$250 per night
4.88 out of 5 average rating, 84 reviews
Superhost
Home in Kahuku
Spectacular golf course front steps from the beach
Dec 2 – 9
$368 per night
4.89 out of 5 average rating, 27 reviews
Guest favorite
Home in Hauula
Punalu'u Ocean Paradise - Oceanfront Beach House
Feb 17 – 24
$518 per night
4.95 out of 5 average rating, 21 reviews
Guest favorite
Home in Waialua
Private Ocean Oasis - 3 Bed / 1 Bath
Aug 20 – 27
$525 per night
4.89 out of 5 average rating, 35 reviews
Guest favorite
Home in Honolulu
Waikiki Gem, Stunning Ocean View, Parking Included
Nov 5 – 12
$280 per night
5.0 out of 5 average rating, 38 reviews
Superhost
Home in Haleiwa
Hale Log Cabins* Beachfront* North Shore Oahu
May 12 – 19
$999 per night
4.7 out of 5 average rating, 10 reviews
Guest favorite
Home in Haleiwa
North Shore Beach House with Ocean View
Apr 22 – 29
$559 per night
4.88 out of 5 average rating, 34 reviews
Superhost
Home in Kahuku
Turtle Bay Hawaiian Paradise Free parking WiFi A/C
Dec 17 – 24
$392 per night
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Hauula
Across the Beach-sunrise A
Nov 15 – 22
$425 per night
4.9 out of 5 average rating, 20 reviews
Superhost
Home in Hauula
Pomaika'i
Nov 24 – Dec 1
$335 per night
4.87 out of 5 average rating, 15 reviews
Guest favorite
Home in Hauula
House near Beach, North Shore, 30 day min.
Apr 25 – May 2
$250 per night
4.97 out of 5 average rating, 33 reviews

Quick stats about vacation rentals in Kailua

Total rentals

400 properties

Rentals with dedicated workspaces

180 properties have a dedicated workspace

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

210 properties are a good fit for families

Total number of reviews

13K reviews

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.

Destinations to explore

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