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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.

Guesthouse in Kailua
Holiday Palms-2 blks fr Kailua Bch/walk to town
Secluded on the side of our Kailua home Holiday Palms is a private one-bedroom cottage, steps from Kailua Beach, tucked away amid tropical palm trees, with your own shady patio. To comply with new HNL vacation rental rules, we only rent to one party in any 90-day period. This means that the unit will be blocked for a total of 90 consecutive nights even if the guests occupy for less than 90 nights. Prices will not be reduced/adjusted based on number of days the rental is actually used/occupied.
$169 per night
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Guest suite in Kailua
Salty, Sandy Kailua Sea Shores, & So Much More
This cozy, beachy bungalow is within a 5-10 minute walk to the world famous Kailua Beach. Listen to the sounds of the waves at night as you relax after your fun-filled beach day. The studio is bright and clean with air conditioning, a full kitchenette, comfy Queen size bed, clean bathroom and a private gated entrance. Kailua is a special community with beautiful beaches, great restaurants, boutique shopping and a relaxed atmosphere. We have the space professionally cleaned after every stay!
$165 per night
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Home in Kailua
Cute & Charming, Minutes to Town and Kailua Beach
Welcome Friends! Hale Bali is perfect for family reunions, special family occasions, medical convalescence recovery, or professional business travel! Share your precious time with your loved ones together in a peaceful, private home. Located in Kailua Beach. Walking distance to shops and the pristine waters of Kailua Beach. ♥Poolside Lounge/Tiki Hut ♥Hi-Speed 1G Internet & Work Space ♥Private! 3 bedroom/2 Bath Home ♥Heated Saltwater Swimming Pool ♥Immaculately Clean - Guaranteed!
$465 per night
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Stay near Kailua's top sights

Photo of Kailua Beach Park
Kailua Beach Park200 locals recommend
Photo of Pillbox Hike
Pillbox Hike178 locals recommend
Photo of Whole Foods Market
Whole Foods Market370 locals recommend
Photo of Kailua Beach Adventures
Kailua Beach Adventures40 locals recommend
Photo of Zippy's Kailua
Zippy's Kailua14 locals recommend
Photo of Boots & Kimo's Homestyle Kitchen
Boots & Kimo's Homestyle Kitchen52 locals recommend

Kailua beach vacation rentals

Rental unit in Kailua
Kailua Sunrise Studio ★ 1 Block to the Beach Park!
$113 per night
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Home in Kailua
Kailua Beach Park - 1 BR Cottage *no cleaning fees
$285 per night
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Home in Kailua
Tranquil Beach Home on Private Lane w/ Pool
$672 per night
Rental unit in Kailua
Charming island style Studio - D D's B B
$110 per night
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Private room in Kailua
The Salty Hibiscus Inn w/Saltwater Pool!
$161 per night
Guesthouse in Kailua
Hale Auliikamalei-Perfect little home near the sea
$120 per night
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Guest suite in Kailua
Kailua Hale Kipa Home away from Home! 30 day min.
$125 per night
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Villa in Kailua
La Bella’s B&B-Nai’a (Dolphin) Suite-walk to beach
$407 per night
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Guest suite in Kailua
🌺Adorable 1 bedroom place, walk to the beach
$150 per night
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Rental unit in Kailua
Unique Apartment in excellent location close to
$167 per night
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Guest suite in Kailua
Relaxing Beachside 1 Bedroom. Private Beach Access
$355 per night
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Rental unit in Kailua
Lanikai Star Guest Studio
$145 per night
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Vacation rentals with pools in Kailua

Home in Kailua
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk
$236 per night
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Home in Kailua
Beautiful 5-Bed Beach House with Resort-Style Pool
$550 per night
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Private room in Kailua
Ocean View with Hot Tub-Monthly
$150 per night
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Private room in Kailua
Pillows in Paradise, Private studios
$170 per night
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Home in Waimanalo
Luxury Waimanalo Beach Lot Cottage, Sleeps 4
$225 per night
Cottage in Kailua
Kailua Beachside Cottage
$285 per night
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Guest suite in Kailua
Papaya Paradise Poolside Studio **Licensed**
$175 per night
Private room in Hawaii Kai
Mauka Apartment
$99 per night
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Cottage in Kailua
Kailua Ohana Cottage close to beach
$315 per night
Home in Kailua
Trendy+Spacious 2BR/2BA, Pool, Kailua Town/Beach
$475 per night
Condo in Waikiki
Modern Sunlit Studio w/ Oceanview - Waikiki Beach
$127 per night
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Condo in Waikiki
Waikiki Studio w/ Ocean Views and Full Kitchen
$108 per night

Kailua house rentals

Home in Kailua
Hale Oahu Cottage by AvantStay | Stunning Beachfront Estate!
$821 per night
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Home in Kailua
The Red Ginger: Large 1 Bedroom
$199 per night
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Home in Kailua
Kailua Oahu Beach Home! Sleeps 4! Minimum 30 Days
$299 per night
Private room in Kailua
Healing space 2. Relax and recharge your energy.
$127 per night
Home in Kailua
Kailua Beach Park - 2 BR Cottage *no cleaning fees
$345 per night
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Home in Kailua
Kailua Beach Cottage
$435 per night
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Home in Kailua
Beautiful! 2 blocks to Kailua Beach
$395 per night
Home in Kailua
Kailua Beach House.
$200 per night
Home in Kailua
____Cute Plantation House in Kailua with AC!!_____
$289 per night
Home in Kailua
Tropical Breeze
$295 per night
Home in Kailua
A New Beautiful Kailua Home, near the beach
$275 per night
Home in Kailua
The Pool House in Kailua with 3,200 sf, 6bed/4bath
$812 per night
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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.

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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