Family friendly Quiet Kailua Beachside lane, steps to lane private beach accessFrom $342/night · Sleeps 4
Windward Beach Town
Kailua Vacation Rentals
Island Living on Oahu's Windward Side
Kailua offers one of Oahu's most peaceful and picturesque vacation settings. Located just 30 minutes from Honolulu, this seaside town is known for its soft white sands, turquoise waters, and small-town charm. With no high-rises in sight, Kailua maintains a residential, beach-friendly vibe ideal for extended stays, family retreats, and romantic escapes.
Popular Activities in Kailua
From your vacation rental, enjoy quick access to outdoor adventures like:
- Kayaking to the Mokulua Islands
- Hiking the scenic Lanikai Pillbox Trail
- Swimming and sunbathing at Kailua Beach Park
- Shopping local boutiques and farmers markets
Key Features of Kailua Vacation Rentals
- Steps from Kailua or Lanikai Beach
- Private lanais, gardens, and outdoor showers
- Beach gear often included (chairs, boogie boards, bikes)
- Quiet neighborhoods right for remote work or extended stays
- Local eateries, cafés, and groceries within walking distance
Right For:
- Families needing space and beach access
- Couples seeking a romantic, secluded getaway
- Remote workers looking for inspiration and tranquility
- Visitors planning longer-term stays in a residential setting
Kailua is more than a beach destination-it's a lifestyle. Book a stay in one of our handpicked Kailua vacation homes and find why travelers return to this corner of Oahu year after year.
Rental Listings
Kailua Vacation Rentals Listings
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Kailua Vacation Rentals Map
Family friendly Quiet Kailua Beachside lane, steps to lane private beach accessFrom $342/night · Sleeps 4
Lanikai Breeze – Contemporary Comfort Steps from the ShoreFrom $1,018/night · Sleeps 10
Kailua Beach Historic Renovated CottageFrom $4,804/night · Sleeps 10
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!From $399/night · Sleeps 4
Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!From $265/night · Sleeps 7
The Pool House: 6 BR Kailua Home with Pool, Walking Distance to Kailua and LanikaiFrom $997/night · Sleeps 15
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
Hale Lani – Heavenly Lanikai Hillside LuxuryFrom $3,245/night · Sleeps 8
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary BedroomsFrom $774/night · Sleeps 8
Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC & Lush YardFrom $937/night · Sleeps 12
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
Serene Lanikai House Near the Beach w/Full Kitchen and Great Outdoor SpaceFrom $239/night · Sleeps 6
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
Mokulua Sunrise Ocean Villa LanikaiFrom $1,077/night · Sleeps 8
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
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottageFrom $140/night · Sleeps 2
Beautiful, Tropical Vacation Rental in Keauhou! STVR-19-366304.From $450/night · Sleeps 6
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.From $211/night · Sleeps 4
Resort-like, Beach-side Kailua Lanikai, Pool, AC, WiFi, Kayaks, 50% DISCOUNTSFrom $629/night · Sleeps 6
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s ShoresFrom $2,350/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
From $342/night
Family friendly Quiet Kailua Beachside lane, steps to lane private beach access
Kailua, Hawaii
★★★★★ 10.0/10 · 6 reviews
Only steps to beach through private street gate, and a short 1.5 mile bike to Kailua town. 2 bedrooms, family room, and kitchen on 2nd floor;...
From $1,018/night
Lanikai Breeze – Contemporary Comfort Steps from the Shore
Kailua, Hawaii
★★★★★ 10.0/10 · 6 reviews
Lanikai Breeze is a stylish 5-bedroom vacation rental just steps from the powdery sands of Lanikai Beach, offering a perfect blend of luxury and...
From $4,804/night
Kailua Beach Historic Renovated Cottage
Kailua, Hawaii
★★★★★ 10.0/10 · 6 reviews
The Kailua Beach Historic Cottage is a beautifully renovated 1937 plantation-style beach house just steps from world-renowned Kailua Beach. Blending...
From $399/night
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
Kailua, Hawaii
★★★★★ 10.0/10 · 5 reviews
Indulge in an Unforgettable 30+ Night Stay at Our NEW Luxury Beach House at Kailua BeachImportant Compliance Notice: This home is available only for...
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 $997/night
The Pool House: 6 BR Kailua Home with Pool, Walking Distance to Kailua and Lanikai
Kailua, Hawaii
★★★★★ 10.0/10 · 4 reviews
The Pool House is a spacious 6-bedroom, 4-bath vacation retreat in Kailua offering 3,200 square feet of living space and a private saltwater pool...
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 $3,245/night
Hale Lani – Heavenly Lanikai Hillside Luxury
Kailua, Hawaii
★★★★★ 10.0/10 · 3 reviews
Hale Lani is a serene hillside retreat overlooking Lanikai Beach, offering panoramic views of the Pacific and Mokulua Islands. This 3-bedroom, 4-bath...
From $774/night
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
Kailua, Hawaii
★★★★★ 10.0/10 · 2 reviews
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park -...
From $937/night
Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC & Lush Yard
Kailua, Hawaii
★★★★★ 10.0/10 · 2 reviews
Lanikai Seashore is a stunning beachfront sanctuary in Kailua, HI, where you can experience the vivid beauty of Lanikai Beach just beyond your...
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 $239/night
Serene Lanikai House Near the Beach w/Full Kitchen and Great Outdoor Space
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property...
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 $1,077/night
Mokulua Sunrise Ocean Villa Lanikai
Kailua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Mokulua Sunrise is a luxurious 4-bedroom oceanfront villa in Lanikai offering panoramic views of the Mokulua Islands and direct access to one of...
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 $140/night
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Kailua, Hawaii
★★★★★ 9.8/10 · 79 reviews
Enjoy a restful respite in this private cozy cottage with a beautiful private garden. The Lanikai Bungalow is a private separate cottage. It has one...
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 $211/night
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
Kailua, Hawaii
★★★★★ 9.8/10 · 74 reviews
This beautiful hillside cottage with stunning ocean view offers the perfect getaway for a couple, small family, or up to four vacationers . Ideal for...
From $629/night
Resort-like, Beach-side Kailua Lanikai, Pool, AC, WiFi, Kayaks, 50% DISCOUNTS
Kailua, Hawaii
★★★★★ 9.8/10 · 74 reviews
We offer a solar-heated Pool, AC , WIFI, Kayaks, and up to 50% Discounts on monthly rentals. This property is a 2 1/2 to 3 min walk from the sandy...
From $2,350/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...