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Latest Vacation Rentals in Kailua HI (25)

1 Br Apartment Vacation Rental In Kailua, Hawaii

Kailua Absolutely Oceanfront Deluxe Vacation RentalOne of the few Legal short-term rentals (Less than 30 days)The closest house to the Ocean in KailuaA secluded beach, often no one is in...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Set along Kailuana Loop on Oahus beautiful windward coastline, Hale Ohana by Gather offers a spacious, family-friendly retreat designed for easy island living. With nearly 3,000 square feet of...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Nestled in the beachside community of Lanikai, Kailua, this fully furnished home is over 1400 square feet of luxury living. Beautifully yet simply decorated, this unit is the whole upper half of...

Created Jul 20, 2026

5 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Just steps from one of the most beautiful tourist-free beaches on the island of Oahu, this Hawaiian style home is a perfect peaceful getaway for your extended family. Listen to the waves crashing...

Created Jul 20, 2026

1 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

TA-006-302-3104-01Beautiful ocean front home at the beginning of Oahu's famous Lanikai Beach!. 2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking...

Created Jul 20, 2026

1 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Kailua's Lofty Bungalow is a premier private luxury bungalow getaway - Modern design mingles with traditional elegance in this newly built bungalow. Beautifully furnished with comfort and ease....

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush landscaping, beautiful palm trees and...

Created Jul 20, 2026

6 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-...

Created Jul 20, 2026

6 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.This luxurious Kailua Villa is located on the ocean which is hidden in...

Created Jul 20, 2026

6 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Prices start at $36,000/month and will not be pro-rated based on the length of stay. Please inquire for an accurate quote.Welcome to Kailua Beach Villa. This luxury beachfront home is perfect for...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

If you're looking to work remotely, travel for work, remodel your home & have a place to live while it's worked on then this is the perfect home. This is a redesigned and remodel home that was...

Created Jul 20, 2026

1 Br Guest House Vacation Rental In Kailua, Hawaii

A private setting in a detached home on a wonderful street! The longer the reservation the better, please contact for details. To answer the most common question, yes, we are 'steps' away: 80...

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

ORCHID HOUSETA # 087-311-0016-01With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world....

Created Jul 20, 2026

3 Br Cottage Vacation Rental In Kailua, Hawaii

This fully furnished 2-bedroom, 2-bath 2-story cottage is part of a private, gated, rambling plantation-style property. The 2nd level unit (not equipped for handicapped) catches the ocean breezes...

Created Jul 20, 2026

1 Br Apartment Vacation Rental In Kailua, Hawaii

Welcome to our newly renovated 1-bedroom apartment in Kailua, Oahu. This rental offers everything you need for a comfortable stay, providing a family-friendly atmosphere that will make you feel...

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

This adorable pup-friendly, 3 bedroom, 1 bath vacation rental is ideally located, walking/biking distance to both the quaint shops and eateries of Kailua Town and renowned Kailua Beach! Fill your...

Created Jul 20, 2026

1 Br Apartment Vacation Rental In Kailua, Hawaii

Bring your swimsuit, everything else you need is already here. Our guest house is the perfect location, close to the beach and Kailua town. A large one bedroom guest house with its own private...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

ABSOLUTELY FABULOUS very large two bedroom two bath house or more.... if you rent the loft which has another HUGE bedroom bath and kitchenette. .Sparkling pool in a private courtyard in the back...

Created Jul 20, 2026

2 Br Apartment Vacation Rental In Kailua, Hawaii

Welcome to Heavenly Hale, a spacious and beautifully renovated second-floor residence located in the heart of Lanikai, one of Oahu's most desirable beach communities. Just a short walk from world-...

Created Jul 20, 2026

6 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use...

Created Jul 20, 2026

1 Br Cottage Vacation Rental In Kailua, Hawaii

State of Hawaii Transient Accommodation Registration: TA # 197-713-5104-01In compliance with the revised ordinances of the City and County of Honolulu, the minimum rental period for this property...

Created Jul 20, 2026

1 Br Apartment Vacation Rental In Kailua, Hawaii

RESERVATIONS: 2 NIGHT MINIMUM ... 8 NIGHT MAXIMUM . . BOOKINGS OF 8 Nt's OR MORE REQUIRE THE HOST'S CONSENTMID-STAY CLEANING; $100, REQUIRED FOR 10 Nt's OR MORE2 PERSON ACCOMODATION ONLYADULTS...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Just a 60 second walk from world-famous Lanikai Beach, this unique 2-bedroom setup offers two private 1-bedroom studios. Each studio features its own kitchenette, dining area, sofa, private...

Created Jul 20, 2026

1 Br Private Vacation Home Vacation Rental In Kailua, Hawaii

Contact host for updated calendar. Come and experience life on the lake! This 750 sq ft, second floor one bedroom, one bath with kitchenette, private lanai and private entrance is just what you are...

Created Jul 20, 2026

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