Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

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Guest favourite

Home in Kailua

4.9 out of 5 average rating, 309 reviews

Kailua Beach Park - 2 BR Cottage

Kailua Beach is 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 two minutes walk to step into the ocean at the beach. This a legal vacation rental, license1990/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 shower, sink and plumbing fixtures April 2022!

Top guest favourite

Place to stay in Kailua

4.96 out of 5 average rating, 110 reviews

Honu Suite at La Bella’s-Walk to Beach-Licensed

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.

Guest favourite

Home in Waikiki

4.98 out of 5 average rating, 105 reviews

Waikiki Gem, Stunning Ocean View, Parking Included

Wake up to breathtaking ocean views from our newly renovated 1BR, 1BA condo. Relax on the lanai, let in the gentle breezes, and soak in the picturesque surroundings. With enough space for up to 4 guests, this retreat is perfect for couples, small families, or close friends seeking solace and tranquility. Immerse yourself in the calming ambiance of modern furnishings and a soothing color palette. Convenient parking included. Discover a blissful sanctuary where serenity and relaxation harmonize.

Guest favourite

Home in Kailua

4.96 out of 5 average rating, 28 reviews

Large Kailua Beach Home - Steps To The Beach!

Spacious home for the entire family to enjoy! Just a few minutes walk to the soft sand & clear water of Kailua beach. Spend your days at the beach with your private, air conditioned oasis awaiting you for rest and relaxation. A short bike ride to Kailua Town with restaurants and shops. Lanikai Beach is less than a 5 minute drive away. Hike, bike ride, snorkel, swim, surf, boogie board, kayak, paddle board, kite surf, wind surf, and much more!! Some dates not shown - reach out to confirm avail!

Top guest favourite

Apartment in Kahuku

4.99 out of 5 average rating, 271 reviews

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo nestled in the dreamy North Shore of O‘ahu. Our home is located in the gated community of Kuilima Estates West, within the renowned Turtle Bay Resort. You'll be just a 5–10 minute walk from breathtaking shorelines, world-class surf spots, romantic dining experiences, and endless adventures by land and sea. Kuilima Estates is also the only area on the North Shore where vacation rentals are legally permitted—offering you a unique and worry-free island escape.

Guest favourite

Apartment in Waianae

4.97 out of 5 average rating, 284 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Guest favourite

Cottage in North Shore

4.96 out of 5 average rating, 165 reviews

Luxurious Beach Front Oasis Steps to the Ocean

A hidden gem on the North Shore. The cottage is located on a private, gated, 2 acre ocean front property in the quiet and peaceful area of Mokuleia. The beach is the most secluded on the North Shore as there is no public access so at times it is just you and the lone turtle sunbathing on the beach. The cottage has top of the line appliances, sub-zero and viking. The bed feels like heaven and you have your choice of soaking in the free standing tub or showering under the stars.

Superhost

Flat in Kailua

4.94 out of 5 average rating, 31 reviews

Private waterfront studio with pool and lake view

Beautiful and private lakefront studio with pool and dock. The location is ideal. It is quiet and peaceful yet less than a mile from Kailua town shopping, dining, and entertainment.Kailua beach is less than 5 minutes away. Beach chairs, umbrella and beach wagon available I must list as monthly rental due to new regulations by city and county of Honolulu. Rentals must be no less than 30 days. Max : 2 people listed on agreement. No additional guests. No overnight guests.

Guest favourite

Guest house in Makaha Valley

4.94 out of 5 average rating, 108 reviews

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.

Top guest favourite

Flat in Waikiki

5 out of 5 average rating, 167 reviews

Nine Thousand Waves

This modern studio was personally renovated and designed to be my home while in Hawaii - prioritizing quality, function, and comfort. - Unbeatable location! Steps to Waikiki, Ala Moana Beach, and Ala Moana Mall - Newly renovated and designed - High speed internet + WIFI (for those living that remote life!) - Parking available ($32/night - this is cheap for Waikiki) - Laundry room right next to the unit (accessible via app).

Superhost

Guest house in Kailua

4.79 out of 5 average rating, 156 reviews

Kailua Beach Cottage - 1990/NUC-1797

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Top guest favourite

Guest house in Kailua

4.83 out of 5 average rating, 18 reviews

Lanikai Kailua 1-bedroom apartment

This beautiful, hillside apartment is a 5-minute walk to Lanikai Beach. Part of a residential home, private entrance, 400 sf plus lanai (deck) and small yard. Fully equipped kitchenette, table & chairs, couch, free WiFi. This space is ideal for a single professional person who enjoys a quiet environment. It is not suitable for infants and children. Please note that the minimum stay is 30 nights or more.