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Kailua vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Kailua

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

Superhost
Guesthouse in Kailua
Koolau Loft
Koolau Loft is our guesthouse with beautiful mountain views located in the heart of Kailua. The home has its own private entrance and is located up one flight of stairs. There is one covered parking spot reserved for our guests and more parking located on the street. The home is about a 15 minute walk to Kalama's beach park and a 5 minute walk to the center of Kailua Town, where there is a WholeFoods, Target, and multiple bars and restaurants. Note: there is no laundry on site for our guests.
$105 per night
Superhost
Guest suite in Kailua
Kailua Cottage
Charming attached cottage 2.5 blocks from famous Kailua beach. Totally private with own entrance, kitchen, bathroom, bedroom and living area. TV, WiFi and DVD player available to make your stay comfortable. Reserved parking for one car and access to your own private washer and dryer. Super comfy and cleaned using recommended COVID-19 guidelines. Beach towels, umbrella, and cooler for trips to the beach and an outdoor shower to rinse off when you return. Feel free to message with inquiries.
$118 per night
Superhost
Guesthouse in Kailua
Kailua Palm Studio. Walk to Beach! PERMITTED
Licensed, legal 90/BB-0002 short term rental. *not impacted by Bill 41 (2022) **NEWLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Private residence at the end of a quiet cul-de-sac with friendly neighbors. Rated #1 on Trip Advisor the past 10 years. Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Cynthia Rubinstein Real Estate, Inc. (License #RB-16858)
$315 per night

Stay near Kailua's top sights

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

Kailua beach vacation rentals

Superhost
Home in Kailua
Tropical Hideaway Near the Beach
$80 per night
Superhost
Home in Kailua
Kailua Beach Park - 1 BR Cottage
$264 per night
Superhost
Guest suite in Kailua
The Perfect Escape
$100 per night
Superhost
Guesthouse in Kailua
5 min Walk to famous Kailua Beach
$205 per night
Superhost
Apartment in Kailua
Lanikai Star Guest Studio
$165 per night
Superhost
Apartment in Honolulu
Modern Clean Waikiki Studio Full Kitchen Free Park
$186 per night
Superhost
Apartment in Honolulu
Stunning Island Gem in Central Waikiki
$190 per night
Superhost
Condo in Honolulu
🥥 Retro Modern Waikiki Studio 🌴 21st FLOOR
$143 per night
Superhost
Home in Kaneohe
Private Kaneohe Bay suite-separate entry
$185 per night
Superhost
Condo in Kahuku
North Shore Oahu Getaway at Turtle Bay Resort
$238 per night
Superhost
Condo in Honolulu
Sleek & Sexy SKY Cabana 29th Floor
$187 per night
Superhost
Condo in Kahuku
SEArider TWO at Turtle Bay (1 bedroom / 1 bath)
$383 per night

Kailua home rentals

Superhost
Home in Hauula
Beachfront Sunrise Home/Snorkel/Sunrise/Car Rental
$427 per night
Superhost
Home in Honolulu
1 Bed Cottage close to Waikiki beach.
$129 per night
Superhost
Home in Honolulu
Beautiful Two Bedrooms, Gated & Private Entrance
$388 per night
Superhost
Home in Laie
Beachfront Retro 2 Bedroom Cottage | 30 Days
$518 per night
Superhost
Home in Honolulu
Kahala Sunrise TA 078.419.7632.01
$115 per night
Superhost
Home in Honolulu
Fantastic View, Waikiki DiamondHead
$206 per night
Superhost
Home in Kaneohe
Perfect way to explore Oahu! Kaneohe 30 days
$238 per night
Superhost
Home in Honolulu
NEW-Mountain RV-NO.7-Open Free parking!
$137 per night
Superhost
Home in Kahuku
Hawaiian Country Retreat - 30 day stays
$198 per night
Superhost
Home in Laie
Laie Temple Lane Studio - MONTHLY
$199 per night
Superhost
Home in Hauula
Hauula Studio
$131 per night
Superhost
Home in Hauula
Private Waterfront House AC & Fast Wi-Fi 30 Day
$125 per night

Beach home rentals in Kailua

Superhost
Home in Laie
3 Bdrm, Beach view, Family friendly, A/C, 30-Day
$372 per night
Superhost
Home in Haleiwa
Oceanfront Oahu North Shore Hawaii Private 3b Home
$881 per night
Superhost
Home in Haleiwa
Sunset & V-land Surfers Paradise
$496 per night
Superhost
Home in Kailua
Cozy Kailua Cottage
$98 per night
Superhost
Home in Kailua
Tropical Cottage w/Pool, Lanai & AC, Walk to Beach
$236 per night
Superhost
Home in Kailua
Tranquil Beach Home on Private Lane w/ Pool
$415 per night
Superhost
Home in Kailua
Pilipu Palms 2
$599 per night
Superhost
Home in Kailua
Steps to quiet part of Kailua Beach, AC, New Reno
$150 per night
Superhost
Home in Kailua
Gateway to Lanikai in Kailua-Near Kailua Beach
$175 per night
Superhost
Home in Kailua
Beautiful 5-Bed Beach House with Resort-Style Pool
$529 per night
Superhost
Home in Kailua
Private yard, 8 min walk to Kailua beach
$168 per night
Superhost
Home in Kailua
Villa Frangipani, Kailua Beach
$600 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.


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.

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