
House vacation rentals in Kailua
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Top-rated house rentals in Kailua
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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!

Family Home, Center of North Shore, - Ocean Views!
Legal Nightly Vacation Rental in the heart of North Shore A cozy, island-style family home with 4 bedrooms plus a loft bedroom (5 rooms total). This home includes high-speed WiFi, an 85-inch smart TV, split-unit AC in every room, an outdoor shower, a tree-surrounded porch with sunset views. Walking distance to Waimea Bay and other scenic spots, & just a short drive to restaurants, grocery stores, & other activities. If not available on ur dates we have another family home, just message us!

Beautiful 4-BR Home| Near Beach| Mountain View
A tastefully designed 4 bed/2.5 bath home in a gated community (built in 2022), nestled in the beautiful Makaha Valley. Private back yard with breathtaking Waiâanae Mountain view and peek-a-boo oceanview. Enjoy quality time with your family and friends at this stylish, cozy home. Experience true taste of paradise on western side of Oahu, away from hustle and bustle of city. The endless beaches along the coastline, amazing sealife, and magnificent mountains will make your vacation memorable!

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.

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!

3BR New Construction w/Mt views, Close to Beach
â E komo mai â Imagine vacationing in a brand new home set in a peaceful valley. You're surrounded by Kaâala & Waianae mts, towering palms, mango trees, wild peacocks, & famous beaches. You take a sunrise/sunset stroll around the gated neighborhood (w/24hr security) and return home for a peaceful dinner. Staying in winter? Spot whales & dolphins at the coast & watch waterfalls in the surrounding mountains. Year-round there's surfing, snorkeling, turtle-spotting, rainbows, & nearby hiking.

Kalo Homes - Makaha's Hidden Gem
Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

Oahu Perfect Vacation â˘Pool, Near Beach, Sleeps 14
Aloha! Welcome to Paradise Mahalo! Nestled in stunning mountains and ocean views, enjoy our modern, luxurious and cozy home located in the majestic MÄkaha Valley. Whether it's a few rounds of golf, a hiking trails near by or a five minute drive down to the world famous MÄkaha Beach - you got it all. From the mountains of Yosemite to the beaches of Gulf Shores, my family and I will provide you with the best experience for any vacation and occasion! (Pool available May 7th, 2025)

Family Oceanview Oasis, Hot Tub, 5min to beach
Why guests LOVE our home? Why guests find it such a great VALUE? - Free parking for 5 cars (save $40â$100/car nightly) - Private SPA & BBQ, full kitchen to cut dining costs, - Spacious single-story for large family with senior and kids, 3 bedroom, 9 beds and 2 bathroom - Repeat guest favourite, peaceful spot near beaches & away from Waikiki crowds. - Gated community with Oceanview pool, gym & mountain views, - Filtered water (no bottled runs), - Washer/dryer to travel light

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10
Enjoy time w/family at this new 3 bdr 2.5 bath house in the mountains of Makaha Valley in a gated community. Minutes from year round surf&golf. This is a LEGAL vacation rental. Private yard on perimeter lot with unobstructed ocean&mountain views & just a few min. drive to clean, sand bottom beaches. Please note there is an attached studio on the property but everything is separate&private. Any combination of 10 guests is OK as long as no more than 8 adults.

Kahala Sunrise TA 078.419.7632.01
Experience breath-taking ocean views on the top of Maunalani Heights. This luxury 1 bedroom/1 bathroom home comes with your own private entrance and is tucked away in a quiet residential neighborhood. Very centrally located with a 10-15 minute drive to Waikiki, Diamond Head and Lanikai beach. We recommend after a long day of exploring returning back to this tranquil retreat to relax and enjoy the cool breeze. Lots of street parking TA 078.419.7632.01

Hawaiian Pakele (escape)
Aloha and welcome to our home!! Newly built and luxuriously appointed, this beautiful 3 bedroom and 2.5 bathroom house is the ideal spot on the west side of Oahu. Located in the private gated community, with breath taking views of ocean and mountains and only a 3-min drive to the world famous Makaha beach. This is the most desirable location for families, friends and couples to escape, relax and enjoy a rejuvenating and memorable vacation!
Popular amenities for Kailua house rentals
House rentals with a pool

Westside Hawaiian Sanctuary-New Home w/ 24hr Gated

Le'ale'a by AvantStay | Ocean + Mountain Views!

Top 5% Family-Friendly Home By Beach -Honu Hideout

Makaha Hale - Serene 3 BR Home

LAST MIN Lagoon Tower by Hilton- 2 bedroom Aloha

Sunny Heaven 1 Bd Plus Loft

Ocean Pearl

~New~ Hale Kai at Turtle Bay Golf Course
Weekly house rentals

Brand New 4BR Home! Ocean and Mountain View!

Waimea Bay Tropical Retreat w/ pool & jacuzzi

"Pineapple Perch" | Fully Renovated | A/C in Every

Lanikai ocean view home

A/C Surfer family home 3 minutes walk to the beach

Relax Hawaiian Style

"Coconut Crest Cottage"

Haleiwa Dream Location
Private house rentals

4 Bedroom Luxury Home in Makaha Valley

Hale Mahina Beach House

Kamalani's Hale, beachfront- 30 day minimum stay

Golf Course View - 2 Bed and 2.5 Bathrooms

NorthShore Tropical Beach house

Peek-a-Boo Ocean View

Modern Waikiki Retreat â 1 Block from the Beach!

Spacious 4BR Laie home- Walk to Hukilau Beach 30
Quick stats about house rentals in Kailua
Total rentals
190 properties
Nightly prices starting at
R695Â ZAR before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
60 properties have a pool
Destinations to explore
- Honolulu Vacation rentals
- Oâahu Vacation rentals
- Kauaʝi County Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikiki Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kihei Vacation rentals
- Kona Vacation rentals
- Kaanapali Vacation rentals
- Hilo Vacation rentals
- Princeville Vacation rentals
- North Kona Vacation rentals
- Apartment rentals Kailua
- Rentals with a patio Kailua
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- Rentals with a hot tub Kailua
- Rentals with a washer and dryer Kailua
- Rentals with beach access Kailua
- Pet-friendly rentals Kailua
- Condo rentals Kailua
- Beach condo rentals Kailua
- Rentals with pools Kailua
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- Waterfront rentals Kailua
- Beachfront rentals Kailua
- Family-friendly rentals Kailua
- Rentals with a kayak Kailua
- Villa rentals Kailua
- House rentals Honolulu County
- House rentals Hawaii
- House rentals United States
- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- MÄlaekahana Beach
- Honolulu Zoo
- Ala Moana Beach Park
- Banzai Pipeline
- MÄkoa Beach
- Kalama Beach
- Hanauma Bay
- Kapiolani Park Beach
- White Plains Beach
- Sans Souci Beach
- Bishop Museum
- Kahala Hilton Beach
- Wet 'n' Wild Hawaii
- Nimitz Beach
- Diamond Head Beach Park
- Pyramid Rock Beach
- Ke Iki Beach
- Kalani Beach
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Nature and outdoors Honolulu County
- Wellness Honolulu County
- Entertainment Honolulu County
- Sports activities Honolulu County
- Art and culture Honolulu County
- Things to do Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Tours Hawaii
- Entertainment Hawaii
- Nature and outdoors Hawaii
- Food and drink Hawaii
- Art and culture Hawaii
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States