Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!From $265/night · Sleeps 7
Quiet Windward Beach Neighborhood
Lanikai Vacation Rentals
Why Lanikai Is a Premier Destination
Lanikai, located just south of Kailua, is widely considered one of the most beautiful and elite neighborhoods in Hawaii. With powder-soft sands and calm turquoise waters, Lanikai Beach is the crown jewel of Oahu's windward coast. This residential enclave provides unmatched serenity and visual splendor – a favorite for those seeking luxurious seclusion paired with outdoor adventure.
Luxury Amenities and Design
- Spacious estates with ocean-view lanais and lush tropical gardens
- Private pools, chef kitchens, outdoor showers, and smart home systems
- Direct beach access or a short stroll to the shoreline
- Premium finishes and decor tailored for upscale travelers
Activities & Nearby Attractions
- Kayaking to the Mokulua Islands (launch from the beach or Kailua Beach Park)
- Hiking the Lanikai Pillbox Trail for sunrise views over the ocean
- Shopping and dining in Kailua town, with cafes, boutiques, and farmers markets
- Snorkeling, paddleboarding, and swimming in calm reef-protected waters
Who These Rentals Are Right For
- Luxury travelers seeking privacy and beachfront indulgence
- Couples and honeymooners looking for an elegant, romantic setting
- Families and groups needing upscale amenities and spacious layouts
Lanikai luxury rentals blend refined island living with natural beauty. Whether you're waking to the sound of surf or admiring the sunrise over the Mokulua Islands, every moment here is designed for peace, privacy, and unparalleled comfort. Browse our listings to find your right stay in Lanikai - or explore more options nearby in Kailua vacation rentals.
Rental Listings
Lanikai Vacation Rentals Listings
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Lanikai Vacation Rentals Map
Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!From $265/night · Sleeps 7
Kailua Condo / Townhouse on Oahu 7 day per 30 day periodFrom $383/night · Sleeps 5
Upscale Kailua Getaway: Steps to Swim Beach!From $1,580/night · Sleeps 6
Luxury beachfront villa on a world class beach in Kailua, HIFrom $4,254/night · Sleeps 18
World Famous Kailua Beach Charming CottageFrom $103/night · Sleeps 2
Bright and airy 1-bedroom cottage in charming Kailua, 1 block to beach. WiFi, ACFrom $257/night · Sleeps 2
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to BeachFrom $815/night · Sleeps 10
Orchid House - Pool and Endless Ocean views!From $1,021/night · Sleeps 7
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media RoomFrom $1,029/night · Sleeps 12
Lokomaika'i Kailua: Elegant Vacation Home with Pool & ACFrom $1,080/night · Sleeps 11
Romantic Oceanview Guesthouse - Studio. Steps from the Beach!From $220/night · Sleeps 2
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01From $200/night · Sleeps 2
Tradewind Bungalow, in Kailua on OahuFrom $186/night · Sleeps 5
Steps to the Beach GuesthouseFrom $231/night · Sleeps 2
Zen Home Near Kailua Beach. Ask For Short StaysFrom $1,176/night · Sleeps 12
Beautiful, Tropical Vacation Rental in Keauhou! STVR-19-366304.From $450/night · Sleeps 6
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s ShoresFrom $2,850/night · Sleeps 14
Kahela - Paradise for RentFrom $665/night · Sleeps 8
Ohana Beach House - 5 Bedrooms - Steps Away from Kailua BeachFrom $1,080/night · Sleeps 10
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, KailuaFrom $400/night · Sleeps 8
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the BeachFrom $216/night · Sleeps 6
Kailua Home Pool & Spa with amazing viewsFrom $340/night · Sleeps 7
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!From $409/night · Sleeps 6
Classic Kailua Beach House – Oceanfront Bliss in Windward OahuFrom $2,350/night · Sleeps 10
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua BeachFrom $3,093/night · Sleeps 16
Huge House Near Kailua Beach, Short Stay AvailableFrom $1,463/night · Sleeps 20
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet okFrom $298/night · Sleeps 4
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront HomeFrom $2,550/night · Sleeps 12
New Listing: Spacious Suite for 4x with panoramic ocean viewFrom $154/night · Sleeps 4
Kailua Palms Guest House with Pool and Views! Parking and wi-fi includedFrom $591/night · Sleeps 4
1 Bdrm Ocean View walk to Turtle Beach, close to Kona Village&Magic Sands BeachFrom $129/night · Sleeps 2
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor livingFrom $461/night · Sleeps 4
Absolutely Oceanfront - 60' Waterfall Lap PoolFrom $556/night · Sleeps 2
From $265/night
Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!
Kailua, Hawaii
★★★★★ 10.0/10 · 4 reviews
Say aloha to this beautiful vacation rental in east Oahu! This Kailua home features 3 bedrooms, 2 bathrooms, a well-equipped kitchen, and a peaceful...
From $383/night
Kailua Condo / Townhouse on Oahu 7 day per 30 day period
Kailua, Hawaii
★★★★★ 10.0/10 · 3 reviews
”Aloha and Welcome Home" message me on availability as it can only be rented once in a 30 day period. Ordinance 19-18 does not require a renter to...
From $1,580/night
Upscale Kailua Getaway: Steps to Swim Beach!
Kailua, Hawaii
★★★★★ 10.0/10 · 3 reviews
This Kailua vacation home is a luxury 3-bedroom retreat just steps from Oahu's iconic Lanikai Beach. Ideal for families or small groups, this...
From $4,254/night
Luxury beachfront villa on a world class beach in Kailua, HI
Kailua, Hawaii
★★★★★ 10.0/10 · 2 reviews
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...
From $103/night
World Famous Kailua Beach Charming Cottage
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Studio Cottage near Kailua Beach and Beach Park! Large, 200 square foot lanai, fully furnished. Nice neighborhood setting. You won't believe how...
From $257/night
Bright and airy 1-bedroom cottage in charming Kailua, 1 block to beach. WiFi, AC
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
This sunny cottage in Kailua is a perfect choice for guests seeking a quiet retreat in a fantastic location, so conveniently close to all that Kailua...
From $815/night
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Set along Kailuana Loop on Oahu’s beautiful windward coastline, Hale Ohana by Gather offers a spacious, family-friendly retreat designed for easy...
From $1,021/night
Orchid House - Pool and Endless Ocean views!
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Orchid House is a newly renovated 3-bedroom, 4-bath custom retreat in Lanikai, offering magical views of the Mokulua Islands from most rooms....
From $1,029/night
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Villa Hui Hou is a newly renovated 5-bedroom, 4.5-bath luxury retreat in Lanikai, Oahu, accommodating up to 12 guests. Just steps from the beach, it...
From $1,080/night
Lokomaika'i Kailua: Elegant Vacation Home with Pool & AC
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Lokomaika'i Kailua is a gracious island retreat just steps from the sands of Kailua Beach, with a private backyard gate to a scenic beach path. This...
From $220/night
Romantic Oceanview Guesthouse - Studio. Steps from the Beach!
Kailua, Hawaii
★★★★★ 9.8/10 · 180 reviews
Just a two minute (75 yard) walk to beautiful Kailua Beach using our private beach access! Air conditioning and Wifi included. This lovely...
From $200/night
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01
Kailua, Hawaii
★★★★★ 9.8/10 · 170 reviews
Start your day with a stroll on one of the most beautiful beaches in the world. Enjoy the sunrise in Kailua where your Hawaiian holiday truly begins....
From $186/night
Tradewind Bungalow, in Kailua on Oahu
Kailua, Hawaii
★★★★★ 9.8/10 · 148 reviews
Attractive, spacious ground floor, 2 bedroom, 1 split bathroom unit with a separate living room and private entry. Located on the island of O’ahu,...
From $231/night
Steps to the Beach Guesthouse
Kailua, Hawaii
★★★★★ 9.8/10 · 91 reviews
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...
From $1,176/night
Zen Home Near Kailua Beach. Ask For Short Stays
Kailua, Hawaii
★★★★★ 9.8/10 · 80 reviews
The Kailua Beach Zen Retreat is a beautifully renovated 4-bedroom, 4-bath Hawaiian-style home just a three-minute walk from stunning Kailua Beach on...
From $450/night
Beautiful, Tropical Vacation Rental in Keauhou! STVR-19-366304.
Kailua, Hawaii
★★★★★ 9.8/10 · 77 reviews
This beautiful tropical vacation rental in the Keauhou Resort area of Kailua-Kona, HI is only a block away from stunning Keauhou Bay and across the...
From $2,850/night
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
Kailua, Hawaii
★★★★★ 9.8/10 · 60 reviews
This Kailua Beachfront Estate is a beautifully renovated 6-bedroom vacation rental set directly on the soft white sands of Oahu's renowned Kailua...
From $665/night
Kahela - Paradise for Rent
Kailua, Hawaii
★★★★★ 9.8/10 · 51 reviews
Located just steps from the best part of Kailua Beach. The beach is a short walk through Kailua Beach Park where the waves are the most gentle, the...
From $1,080/night
Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach
Kailua, Hawaii
★★★★★ 9.8/10 · 49 reviews
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...
From $400/night
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
Kailua, Hawaii
★★★★★ 9.8/10 · 45 reviews
Stay in comfort as long as you wish. 30 day minimum lease, shorter stud are of longer stays are welcome. Contact Us for Details and RatesHawaii Tax...
From $216/night
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach
Kailua, Hawaii
★★★★★ 9.8/10 · 32 reviews
One Rate for 7 up to 30 day stay - A 30 day minimum lease.Hawaii Tax ID # available upon requestMountain View's cooling breezes , easy 5 minute walk...
From $340/night
Kailua Home Pool & Spa with amazing views
Kailua, Hawaii
★★★★★ 9.8/10 · 29 reviews
Two story home in Quiet Kailua neighborhood. Master bedroom is overlooking a beautiful pool and spa with views over the town of Kailua and the ocean....
From $409/night
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!
Kailua, Hawaii
★★★★★ 9.8/10 · 21 reviews
This is a short-term vacation rental. Welcome to Hale Alapi'i, our home in fabulous Lanikai!This is a 3b/2b ~1,400 sq. ft. main house that sleeps 4...
From $2,350/night
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
Kailua, Hawaii
★★★★★ 9.6/10 · 144 reviews
This Kailua Beachfront Home is a relaxed oceanfront retreat offering panoramic views of Kailua Bay and the Ko'olau Mountains. Located just minutes...
From $3,093/night
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach
Kailua, Hawaii
★★★★★ 9.6/10 · 88 reviews
Palione Papalani - meaning "Heavenly Sands" - is a newly renovated 6-bedroom luxury vacation rental just steps from Kailua Beach, offering the...
From $1,463/night
Huge House Near Kailua Beach, Short Stay Available
Kailua, Hawaii
★★★★★ 9.6/10 · 84 reviews
Summary:Inquire about short stays – we accommodate them when possible. This spacious, resort-style residence is located just 100 yards from Kailua...
From $298/night
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet ok
Kailua, Hawaii
★★★★★ 9.6/10 · 76 reviews
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This large...
From $2,550/night
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront Home
Kailua, Hawaii
★★★★★ 9.6/10 · 41 reviews
Kailuana Beachfront Estate is a fully remodeled luxury retreat on nearly an acre of prime Kailua Beach oceanfront land. Featuring a main home with 3...
From $154/night
New Listing: Spacious Suite for 4x with panoramic ocean view
Kailua, Hawaii
★★★★★ 9.6/10 · 13 reviews
Our Tropical Treasure is situated at a cool 1300' elevation with a "million dollar view" over looking the ocean. The climate is perfect all year...
From $591/night
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Kailua, Hawaii
★★★★★ 9.6/10 · 13 reviews
Come bask in the gentle trades of the windward side at the Kailua Palms Estate Guest House, a fabulous two bedroom, two bath vacation guest house...
From $129/night
1 Bdrm Ocean View walk to Turtle Beach, close to Kona Village&Magic Sands Beach
Kailua, Hawaii
★★★★★ 9.6/10 · 11 reviews
Cute one bedroom beach side apartment with ocean view in perfect location, on Ali'i Drive across the street from Turtle Beach. Turtle Beach access 2...
From $461/night
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living
Kailua, Hawaii
★★★★★ 9.6/10 · 8 reviews
ABSOLUTELY FABULOUS very large two bedroom two bath house or more.... if you rent the loft which has another HUGE bedroom bath and kitchenette....
From $556/night
Absolutely Oceanfront - 60' Waterfall Lap Pool
Kailua, Hawaii
★★★★★ 9.4/10 · 176 reviews
Kailua Absolutely Oceanfront Deluxe Legal Vacation RentalThe closest house to the Ocean in KailuaLocated in a quiet upscale neighborhood away from...