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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.

Private room · Kailua
Blue Kailua
****Come and Experience the true "SPIRIT of ALOHA" .**** We have Just one Bedroom in our home For "Airbnb", with a Queen Bed. It has it's own door leading to the Shared Bath. Air Conditioned, NETFLIX, Full use of Kitchen, Living Room & Lanai. WE HAVE 2 VERY FRIENDLY FUR BABIES. Free Use of Beach Gear, chairs, boogie boards. (WALKER WITH SEAT, & BICYCLES FOR RENT) $20 30 minute to (Kualoa Ranch & Beach) , 5 min to Kailua's beaches, 30 min North Shore Beach & Polynesian Cultural Center.
Apr 20 – 27
$119 per night
Home · 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!
Mar 11 – 18
$247 per night
Home · Kailua
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Charming Cottage in beautiful Lanikai that has been totally renovated in 2021. Everything in the Cottage is new including the furnishings! Short walk to the beach. Enjoy the comforts of home with an efficient kitchen and own washer and dryer. Large lanai to extend the living space and room to BBQ and dine. One split AC unit adequate to quickly provide comfort. Enjoy the outdoor shower after the beach and refresh in the small pool with gentle waterfall to cool off and relax in the heat of the day. Beautiful tropical garden setting. Privacy and quiet will provide you with the ultimate relaxing setting to enjoy your time in Lanikai. Licensed vacation rental. Ideal for a maximum of 2 adults but we will accept 3 if there are no children in the group or 2 adults and 2 children. There is a small 6ft deep, 10x20 kidney shaped pool with a waterfall perfect for relaxing or small children. This vacation home has been registered as a Transient Accommodation with the State of Hawaii - HAWAII TAX TA-006-174-7200-01 This property is a licensed short term vacation rental, Non-Conforming Use Permit Number NUC# 90/TVU-0325 and is compliant with Hawaii State Legislation for vacation rental accommodations.
Sep 25 – Oct 2
$305 per night

Vacation rentals for every style

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Stay near Kailua's top sights

Photo of Kailua Beach Park
Kailua Beach Park104 locals recommend
Photo of Kailua Beach Adventures
Kailua Beach Adventures28 locals recommend
Photo of Lanikai Pillbox
Lanikai Pillbox37 locals recommend
Photo of Twogood Kayaks Hawaii
Twogood Kayaks Hawaii6 locals recommend
Photo of Aaron's Dive Shop
Aaron's Dive Shop5 locals recommend
Photo of Pillbox Hike
Pillbox Hike63 locals recommend

Kailua beach vacation rentals

Cottage · Kailua
Kailua Cottage - Private Home Close to Beach& Town
Apr 14 – 21
$683 per night
Guest suite · Kailua
Lanikai Beach Rental
Feb 27 – Mar 6
$220 per night
Private room · Kailua
Tropical Oasis in Paradise -- The Pikake
Mar 23 – 30
$175 per night
Villa · Kailua
LaBella’s B&B-Honu (Turtle) Suite- 6 mins to beach
Sep 22 – 29
$350 per night
Home · Kailua
Kailua Beach Park - 2 BR Cottage
Mar 16 – 23
$288 per night
Home · Kailua
Tropical Oasis in Kailua-30 day minimum
Jun 8 – 15
$674 per night
Home · Kailua
Beautiful Kailua Home, Near the Beach
Apr 30 – May 7
$261 per night
Home · Kailua
Hale Oahu Cottage by AvantStay | Stunning Beachfront Estate!
Feb 8 – 15
$717 per night
Guesthouse · Kailua
Kailua Beach Cottage - 90/TVU-0287
Jul 11 – 18
$431 per night
Guesthouse · Kailua
Kailua's Premier Private Luxury Lofty Bungalow
May 15 – 22
$426 per night
Home · Kailua
Charming 4BD w Pool by Kailua Beach
Aug 24 – 31
$807 per night
Condo · Waikiki
High Speed Internet, 1 Block to Beach & New Design
Mar 19 – 26
$108 per night

Kailua home rentals

Home · Kailua
Private getaway
Apr 8 – 15
$310 per night
Home · Kailua
Serenity Beachfront Cottage- NUC No 90/TVU-0326
May 11 – 18
$400 per night
Private room · Hawaii Kai
Best of Oahu - Near Hanauma Bay and Sandy Beach
Dec 27 – Jan 3
$94 per night
Private room · Honolulu
Cozy Secure Comfy Room
Jan 5 – 12
$55 per night
Home · Kaneohe
Ocean view 2 bedroom rental
May 3 – 10
$389 per night
Home · Kaneohe
Spacious 4 bedroom 2 bath
Aug 25 – Sep 1
$643 per night
Private room · Honolulu
Aloha hawaiian Private Room C
Nov 28 – Dec 5
$78 per night
Private room · Kaimuki
Private Island Room- great space and location
Oct 25 – Nov 1
$74 per night
Private room · Honolulu
Small Quaint Private Room
Apr 17 – 24
$55 per night
Home · Kaneohe
Windward Suites
Sep 15 – 22
$356 per night
Home · Kailua
Luxurious 4/5BD in Gated Community
Sep 6 – 13
$829 per night
Home · Kailua
A New Beautiful Kailua Home, near the beach
Jul 25 – Aug 1
$261 per night

Kailua condo rentals

Condo · Waikiki
38th floor Waikiki condo for 2 - amazing views
Aug 24 – 31
$94 per night
Condo · Hauula
Beachfront Condo on Secluded Beach!
Feb 24 – Mar 3
$200 per night
Condo · Waikiki
38th floor Waikiki condo for 3 - amazing views
Jul 29 – Aug 5
$123 per night
Condo · Waikiki
Sep 5 – 12
$110 per night
Condo · Waikiki
Spacious Apartment Central of Waikiki Near Beach!
Oct 23 – 30
$161 per night
Condo · Waikiki
Mountain View Studio with Full Kitchen(Legal)
Mar 15 – 22
$124 per night
Condo · Ala Moana
Ala Moana Hotel 6F
Mar 28 – Apr 4
$80 per night
Condo · Waikiki
8th Floor Waikiki Grand, City View Full Kitchen
Jul 14 – 21
$142 per night
Condo · Waikiki
Waikiki 26th Floor Modern Studio w/ Mountain View
May 19 – 26
$109 per night
Condo · Waikiki
Spacious Studio w/Canal, City & Mt View in Waikiki
Feb 5 – 12
$116 per night
Condo · Waikiki
Islander's OCEAN VIEW-Legal Unit 2 blocks to beach
May 29 – Jun 5
$120 per night
Condo · Waikiki
31st floor Waikiki condo for 4 - walk to the beach
Aug 28 – Sep 4
$118 per night

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.

When is 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.

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.


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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