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Luxury Kailua Vacation Rentals, Beachfront Homes & Villas

Start Your Vacation Rental Search > Hawai’i Vacation Rentals and Villas > Oahu Luxury Vacation Rentals & Villas > Luxury Kailua Vacation Rentals, Beachfront Homes & Villas

Popular Oahu neighborhoods

Aina Haina | Diamond Head | Hawaii Kai | Kahala | Kaka’ako | Kuilima Estates | Lanikai | Makaha | North Shore | Turtle Bay | Waikiki | Waimanalo
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The average night price is $2,052

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    Aerial shot of Kailua Beach Kailua Beach and Mokulua Island views from the edge of your yard. Step directly onto the sandy beach from your private yard. Aerial shot of the pool, courtyard and beachfront location Enjoy the private beachside yard with lush tropical landscaping. Enjoy the lush and ocean views from the lanai. Private access to Kailua Bay's gorgeous white sand beaches

New Listing!

Kailua Beachside

5 Beds
5 Baths
10 Sleeps

Starting at $1,166/night

Holiday Availability

Oahu Lani*

10 Beds
11.5 Baths
12 Sleeps

Starting at $10,000/night

    Tropical lagoon style pool with natural rocks and cascading waterfalls. Relax in the hot tub. Tropical lagoon style pool and spa with natural rocks and cascading waterfalls. Kai Moena Estate Beachfront with over 225 linear feet. Expansive private lawn. Oceanside main house living room access

Holiday Availability

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Kailua's Kai Moena

7 Beds
6.5 Baths
14 Sleeps

Starting at $4,167/night

    Tropical lagoon style pool with natural rocks and cascading waterfalls. Tropical lagoon style pool and spa with natural rocks and cascading waterfalls. Outdoor Poolside Lanai with Sonos speakers Guest house: Billiard room with slider doors to fully open to the inside courtyard. Expansive private lawn. Kai Moena Estate Beachfront with over 225 linear feet.

Holiday Availability

Kailua's Kai Moena Estate

9 Beds
7.5 Baths
18 Sleeps

Starting at $4,667/night

    Manicured Lawns Private Pool at Kailua Shores Estate Kailua Shores Estate - USTA approved private Tennis Court Beach House - Formal Living Main House - Outdoor Lanai and Outdoor Dining Pool House - Open Air Bar Main House - Formal Living

Kailua Shores Estate 8 Bedroom

8 Beds
9 Baths
18 Sleeps

Starting at $2,350/night

    Welcome to unparalleled luxury, where every detail offers a sublime taste of an exquisite Hawaiian vacation. Seamless flow from the kitchen to dining and living spaces, perfect for entertaining and relaxation. Step inside to an expansive open floor plan leading directly to the inviting pool area. Enjoy breathtaking beach vistas from the comfort of your seaside lanai. Dive into your private pool's invigorating, crystal-clear waters. This beachfront villa is located on the famous shores of Kailua Beach. Beachfront villa on the renowned shores of Kailua Beach awaits.

Kailua Beach Villa

5 Beds
5 Baths
12 Sleeps

Starting at $1,667/night

    Relax and unwind by the inviting pool, complemented by comfortable chaise lounges. Enchanting evenings await by the shimmering pool under the twilight sky. A short distance away to the iconic Kailua beach is perfect for engaging in water sports or basking in the Hawaiian sun. The allure of Hale Aloha extends beyond the property itself. Welcome home! Savor your meals in the refreshing embrace of the open air. Relax in this inviting living space, where soft tones and tropical artwork create the perfect island retreat ambiance. Relax in this inviting living space, where soft tones and tropical artwork create the perfect island retreat ambiance.
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Hale Aloha

4 Beds
2 Baths
10 Sleeps

Starting at $1,685/night

    Recline in the sitting room, immediately inside once you cross the threshold into the villa. The view is simply breathtaking. The beautiful tropical oasis is waiting to provide you with unforgettable moments Complete with vaulted ceilings, a stone fireplace, and elegant travertine and wood flooring, Maluhia’s expansive common areas and open flow provide a setting of relaxed luxury for your group’s vacation Cozy up in the living area, which is between the pool, kitchen and barbecue areas - central to all of the action! Its remodeled, modern interior features nearly 5,000 sq. ft. of living space Another view of the sitting room, with the dining room to the right. Views from the front door of the sitting room, pool deck with waterfall, dining room and further is the kitchen.
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Maluhia

4 Beds
4 Baths
9 Sleeps

Starting at $733/night

    Kailua Hale Kahakai is quite beautiful at dusk Enjoy some time in the shaded outdoor seating area with gorgeous tropical views Immerse yourself in the natural beauty of the island right in your backyard Bright and lively living room with sliding doors to your backyard paradise The indoor formal dining area comfortably seats 6 with gorgeous views This open-concept floor plan is aptly fit for entertaining, complete with living room, dining area, and library Enjoy the library, just off of the living area
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Kailua Hale Kahakai

6 Beds
5 Baths
12 Sleeps

Starting at $650/night

    Tranquil pool deck with a jacuzzi and waterfall Relax and unwind in your private hot tub This covered lanai with ceiling fans interconnects with the indoor living area Don't forget about the built-in BBQ to grill up your favorite island meals Rooftop deck with built-in BBQ, lounge, and dining spaces with peekaboo ocean views Indoor/outdoor living at its finest with a beautiful rooftop deck to catch those peekaboo ocean views Gather with friends and family for a meal at the outdoor dining space

Holiday Availability

Hale Ohana

4 Beds
3 Baths
10 Sleeps

Starting at $483/night

    Enjoy views of the tropical landscape and ocean from the front porch Ocean front lanai with brand new lounge set up! More photos to come! The covered front porch is a great place to have your morning coffee or relax after a long day of adventures Cozy living room with all new furniture! Bright and spacious dining space Table can seat six guests Tv space and dining space blend in a beautiful and bright open concept style

Holiday Availability

Kai Mele

3 Beds
2 Baths
6 Sleeps

Starting at $433/night

    Luxury and spaciousness greet you in our living area where an open floor plan invites relaxation and connection. Seahorse Beach House offers the ultimate beachfront experience, nestled close to the shores of Kailua Beach. Perched on an elevated corner lot, enjoy the breathtaking blend of ocean waves and majestic mountain peaks. Luxury meets openness in our front house living room, where an open floor plan invites relaxation and togetherness. A grand welcome awaits at our stunning front house entrance, where first impressions are unforgettable. Front House Where comfort meets nature - our wrap-around deck awaits your arrival.
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Seahorse Beach House

2 Beds
2 Baths
4 Sleeps

Starting at $400/night

    View back towards the primary and covered lanai Living room with extra large sofa, perfect for the whole family to gather! Newly remodeled kitchen with top of the line appliances. Experience the grandeur of a cathedral ceiling in the living area, complemented by a section of glass roofing, allowing an abundance of natural light to cascade in, illuminating the space beautifully. Welcome to Lokomaika'i Kailua! Living room with extra large sofa, perfect for the whole family to gather! Experience the grandeur of a cathedral ceiling in the living area, complemented by a section of glass roofing, allowing an abundance of natural light to cascade in, illuminating the space beautifully.
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Lokomaika'i Kailua

5 Beds
3 Baths
11 Sleeps

Starting at $533/night

    Manicured Tropical Beach Lawn Kailua Shores Estate - USTA approved private Tennis Court Kailua Shores Estate - Pool Kailua Shores Estate by night Luxury Kailua Shores Estate - Beach Front Beach House - Formal Living Tennis House - Formal Living

Kailua Shores Estate 5 Bedroom

5 Beds
5 Baths
10 Sleeps

Starting at $1,600/night

    Property is just steps away from Kailua Beach Proximity to the Beach from Ranch Beach House Private, Calm, and peaceful main lanai and garden area. Large deck with Chaise loungers for soaking up the sun and outdoor seating area. Open floor plan with Vaulted Ceilings and Skylight Dining Room with natural lighting and opens to main lanai and garden area. Private Yard with Large Deck and Chaise Lounge Chairs Private outdoor lanai with outdoor seating
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Ranch Beach House

2 Beds
1.5 Baths
4 Sleeps

Starting at $250/night

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