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Windward Beach Town
Kailua vacation rentals place you near Kailua Beach, Lanikai, kayaking, hiking, local cafes and Oahu’s windward coast. This beach-town area works well for ocean mornings and a local neighborhood feel.
Rental Listings
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Place in Paradise - Kailua Beach Oceanfront Vacation HomeFrom $2,550/night · Sleeps 14
Stunning oceanfront cottageFrom $649/night · Sleeps 2
Walker's Lanikai Beach House – Historic Oceanfront RetreatFrom $3,093/night · Sleeps 14
Koi Palms 1 bedroom Cottage - Great location! 5 Minute...From $317/night · Sleeps 2
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned...From $288/night · Sleeps 2
Available and legal for stays less than 30 days.From $259/night · Sleeps 2
Kailua Oceanfront Villa with Heated Pool & Spa - availability...From $710/night · Sleeps 6
Tropical & inviting home w/spa, torches, waterfalls & ocean viewFrom $784/night · Sleeps 8
From 185 nt Aloha Summer Sizzle 2025 incl AC, 5...From $170/night · Sleeps 5
Beachside Kailua AC 3min walk to beach! Inquire for available...From $778/night · Sleeps 8
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and...From $1,283/night · Sleeps 8
Oceanfront Luxury Condo Closest to BeachFrom $300/night · Sleeps 6
Kailua Beach "The Pink House" 100 Yards from OceanFrom $595/night · Sleeps 6
Kolea Landing Modern Beach House w/ Double Suite and Third...From $644/night · Sleeps 6
3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY...From $449/night · Sleeps 6
Unique Oceanfront Home in Enclosed AreaFrom $630/night · Sleeps 6
licensed NUC no 90/TVU-0326 Serenity Beachfront CottageFrom $674/night · Sleeps 4
Beach Villas at Kahalu‘u, Sunset/Ocean Views, Prime Snorkel/Surf Beach, Pool/SpaFrom $360/night · Sleeps 4
Hale Lanikai – Classic Hawaiian Style Beach House & Guest...From $2,250/night · Sleeps 8
Celebrate America's 250th Birthday & Kailua Fireworks from Beachfront LanaiFrom $1,466/night · Sleeps 8
Happy House on Exquisite Kailua Beachside Property!From $467/night · Sleeps 6
Kailua Beachfront Vacation Home with PoolFrom $2,450/night · Sleeps 10
Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1...From $946/night · Sleeps 10
Lanikai Ocean Front Duplex Bungalow Private ocean steps. Contact for...From $782/night · Sleeps 4
Gorgeous Lanikai Villa with Access to Secluded White Sand BeachFrom $4,392/night · Sleeps 15
Lovely Private Kailua CottageFrom $421/night · Sleeps 4
Hale Mokulua: Lanikai Multi-Home Estate - Sleeps 14From $993/night · Sleeps 14
Lanikai Cottage: Charming Tropical Oasis with Private PoolFrom $695/night · Sleeps 6
Ocean Front Private Residence at Keauhou BAY with Pool &...From $2,940/night · Sleeps 10
Kakela Kai, Beachfront Kailua Home, Private, A/CFrom $1,159/night · Sleeps 10
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun DeckFrom $161/night · Sleeps 2
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool,...From $654/night · Sleeps 8
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua...From $513/night · Sleeps 4
Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable...From $340/night · Sleeps 4
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING...From $1,176/night · Sleeps 10
Beach Studio with private yard in Lanikai - 30 day...From $155/night · Sleeps 2
Family friendly Quiet Kailua Beachside lane, steps to lane private...From $342/night · Sleeps 4
Lanikai Breeze – Contemporary Comfort Steps from the ShoreFrom $1,018/night · Sleeps 10
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full KitchenFrom $227/night · Sleeps 4
🌺 A Place of Peace: where heaven meets the Ocean...From $640/night · Sleeps 4
Steps To Kailua BeachFrom $724/night · Sleeps 7
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...From $997/night · Sleeps 15
Kai Hale: 3 BR Oceanfront Lanikai Beach EstateFrom $1,187/night · Sleeps 6
Kailua Beach Historic Renovated CottageFrom $4,804/night · Sleeps 10
Kailua Condo / Townhouse on Oahu 7 day per 30...From $383/night · Sleeps 5
Upscale Kailua Getaway: Steps to Swim Beach!From $1,580/night · Sleeps 6
Hale Lani – Heavenly Lanikai Hillside LuxuryFrom $3,221/night · Sleeps 8
*Affordable Island Getaway with private yard *From $169/night · Sleeps 2
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach...From $399/night · Sleeps 4
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min...From $688/night · Sleeps 8
Cool retreat at the entrance to Lanikai-Very Close to Beach-3...From $774/night · Sleeps 8
Oceanfront Lanikai Beach Vacation HomeFrom $1,460/night · Sleeps 10
Luxury beachfront villa on a world class beach in Kailua,...From $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...From $239/night · Sleeps 6
Bright and airy 1-bedroom cottage in charming Kailua, 1 block...From $257/night · Sleeps 2
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to...From $815/night · Sleeps 10
Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC...From $937/night · Sleeps 12
Orchid House - Pool and Endless Ocean views!From $1,021/night · Sleeps 7
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen...From $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
Oceanfront Luxury Home in Lanikai- sleeps 8From $1,890/night · Sleeps 8
Romantic Oceanview Guesthouse. Steps from the Beach!From $220/night · Sleeps 2
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01From $191/night · Sleeps 2
Tradewind Bungalow, in Kailua on OahuFrom $186/night · Sleeps 6
Steps to the Beach GuesthouseFrom $231/night · Sleeps 2
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private...From $140/night · Sleeps 2
Zen Home with AC, Pool, Near Kailua BeachFrom $1,176/night · Sleeps 12
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua...From $211/night · Sleeps 4
Beautiful, Tropical Vacation Rental in Keauhou! STVR-19-366304.From $450/night · Sleeps 6
Resort-like, Beach-side Kailua Lanikai, Pool, AC, WiFi, Kayaks, 50% DISCOUNTSFrom $629/night · Sleeps 6
Hale Kolea - Luxury Lanikai Hillside RetreatFrom $2,460/night · Sleeps 12
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s...From $2,593/night · Sleeps 14
Kahela - Paradise for RentFrom $665/night · Sleeps 8
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to...From $400/night · Sleeps 8
Ohana Beach House - 5 Bedrooms - Steps Away from...From $1,080/night · Sleeps 10
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short...From $216/night · Sleeps 6
Kailua Home Pool & Spa with amazing viewsFrom $340/night · Sleeps 7
Sweet Vintage Hawaiian Cottage and Guest House! Great deal in...From $282/night · Sleeps 6
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!From $409/night · Sleeps 6
Peaceful Hawaii Paradise three minutes from Beautiful Beach in a...From $240/night · Sleeps 2
Stylish 1BR Apartment with AC, Full Kitchen & W/D -...From $169/night · Sleeps 4
Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near...From $1,092/night · Sleeps 8
Classic Kailua Beach House – Oceanfront Bliss in Windward OahuFrom $1,798/night · Sleeps 10
Viewhouse in Lanikai BEST LOCATION, LANIKAI NUC 90/BB -0108From $357/night · Sleeps 4
Huge House, Heated Pool, AC, Steps to Kailua BeachFrom $1,463/night · Sleeps 20
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua...From $2,793/night · Sleeps 16
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet okFrom $298/night · Sleeps 4
Paradise Under the Plumeria TreeFrom $267/night · Sleeps 5
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach:...From $444/night · Sleeps 4
Kailua Beachside Studio - Monet RoomFrom $239/night · Sleeps 2
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront HomeFrom $2,221/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...From $591/night · Sleeps 4
1 Bdrm Ocean View walk to Turtle Beach, close to...From $150/night · Sleeps 2
Tranquility BeachfrontFrom $1,091/night · Sleeps 8
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor livingFrom $461/night · Sleeps 4
Absolutely Oceanfront - 60' Waterfall Lap PoolFrom $549/night · Sleeps 2
Ocean View Guest Cottage - 1990/NUC-1797From $499/night · Sleeps 4
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great...From $670/night · Sleeps 10
Tropical Garden Paradise, Check our SUPER AFFORDABLE RATE, Now Air...From $210/night · Sleeps 5
Luxury Beach Vacation House in Kailua BeachFrom $2,410/night · Sleeps 14
🏖️Excellent Ocean View | AC | Concierge Included | vrKCVFrom $165/night · Sleeps 4
Fantastic Beach Front VillaFrom $3,011/night · Sleeps 10
1 bdrm peakaboo ocean view walk to Turtle Beach, Alii...From $129/night · Sleeps 3
Kailua Beach Estate: Historic Property with Large Yard & Ocean...From $700/night · Sleeps 6
Award Winner - Hawaii's Hidden Hideaway - Bed and BreakfastFrom $295/night · Sleeps 3
Ocean View Condo with Large LanaiFrom $137/night · Sleeps 4
RENOVATED Studio By The Ocean!!!From $105/night · Sleeps 2
Steps to beach, pool, garden. April/May Cancellation Special. CALL NOW!From $625/night · Sleeps 6
🏖️Ocean View | Close to Pool & BBQ Area |...From $112/night · Sleeps 4
Open-Plan Lush Garden Home Near Kailua & Lanikai BeachesFrom $372/night · Sleeps 8
Oceanfront Condo Total Remodel 2025 2 Pools Kona Sunsets Private...From $293/night · Sleeps 4
Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and...From $1,180/night · Sleeps 9
Aloha Lil Hawaiiana 🌺From $122/night · Sleeps 2
Kaikea Modern 1Ba Lanikai Cottage: Stylish & Private - 5...From $166/night · Sleeps 2
Ohana Rental Cottage Close to BeachFrom $295/night · Sleeps 6
Private Luxury Home, Steps from the Beach w/ AC, Ranch...From $447/night · Sleeps 4
From $2,550/night
Place in Paradise is a spacious 5-bedroom, 5.5-bath beachfront vacation rental located directly on world-famous Kailua Beach, offering stunning ocean...
From $649/night
This beautifully restored one-of-a-kind oceanfront home has all the charm of yesteryear with the added conveniences and sustainability of today....
From $3,093/night
Walker's Lanikai Beach House is a historic oceanfront retreat on one of Oahu's most beautiful beaches. Originally built in 1934 by Queen...
From $317/night
Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of...
From $288/night
"In order to comply with Oahu's 90 day minimum short term rental laws, we may not advertise to rent for a period shorter than 90 days."Come enjoy...
From $259/night
Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a...
From $710/night
Relax in the beautiful three-bedroom seaside villa in Kailua, where soothing sea waves and soft breezes carry you off. Indulge in the outdoor pool,...
From $784/night
From the moment you arrive at Hale Wailele (Waterfall House), tropical scenes take your breath away. Perched above the Kona Coast, this spectacular...
From $170/night
Island breezes, fragrant blossoms, privacy - Na Hale O Keauhou, Hawaii's Best Kept Secret. This private 2 bedroom, 2-1/2 bath, 2 story town home is...
From $778/night
THIS PROPERTY IS A LEGAL SHORT TERM RENTALCONTACT HOST/RESERVATIONS & DETAILSThis airy, spacious four bedroom Kailua beachside vacation rental home...
From $1,283/night
Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa!...
From $300/night
OCEANFRONT LUXURY CONDO CLOSEST TO BEACH 2br/2ba sleeps (4-6) White Sands Village, Kailua-Kona, Kona Coast, Big Island, Hawaii, USA (20 minutes south...
From $595/night
The Pink House is a charming Hawaiian-style beach retreat just 100 yards from beautiful Kailua Beach. This 3-bedroom, 2-bath home offers an open...
From $644/night
Aloha and Welcome to Kolea LandingA short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house...
From $449/night
E komo mai to Hale Makai, our piece of island paradise in Kailua. Beachside and just three houses from Kailua Beach - you are going to love it...
From $630/night
Kona Onenalo is a ONE-OF-A-KIND property on the beautiful Kona Coast. There are 12 identical and individual homes in this quiet, gated community. The...
From $674/night
Charming beachfront cottage right on Kailua Beach! licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage. This delightful 2 bedroom/1 bath vacation...
From $360/night
Welcome to Surfing Turtle Kona where there are ocean and sunset views from every room. Amazing access to the best snorkeling and surfing reef in...
From $2,250/night
Hale Lanikai is a newly remodeled beachfront vacation rental offering classic Hawaiian charm with modern comforts, located on the soft sands of...
From $1,466/night
Tropical Trade Winds and Unsurpassed Views are from our Beach Front Home. Opens up for full enjoyment of Hawaii's Climate. Our rap-around Lanai...
From $467/night
Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by...
From $2,450/night
Set on nearly an acre of prime Kailua Beach frontage, this newly refurbished 3-bedroom, 3-bath home features a large private swimming pool, flexible...
From $946/night
ALOHA! The Kailua Bliss Beach House is a casual and relaxed beach house in the quiet Beachside neighborhood in Kailua, located on a private street, 1...
From $782/night
Location Location Location! Our Lanikai ocean front location exactly in front of the twin Mokulua Islands provides endless hours of outstanding views...
From $4,392/night
This Lanikai oceanfront villa is a fully remodeled 5-bedroom, 4.5-bath gated estate blending 1918 architecture with a modern beach house design....
From $421/night
Welcome to our newly renovated 1-bedroom spacious and private cottage that is super centrally located in the heart of Kailua. Our cottage is situated...
From $993/night
Hale Mokulua is a beautifully remodeled multi-home estate just steps from the white sands of Lanikai Beach. Perfect for multi-family or group...
From $695/night
Lanikai Cottage is a charming retreat just steps from Oahu's famous Lanikai Beach. Featuring two separate dwellings on one property, this cozy...
From $2,940/night
Enjoy everything Hawaii has to offer in a very private three-acre estate on the shore of historic Keauhou Bay, six miles south of Kailua Kona on the...
From $1,159/night
A comfortable beachfront home set in a security-gated neighborhood with central air condition. Decorated with island style rattan furnishings,...
From $161/night
Tastefully remastered, 1937 cottage + rooftop lanai and BBQ area. The Kailua Beach Hideaway is tucked up on the hillside above the beach park, on a...
From $654/night
Nestled in the coveted Lanikai community of Kailua, Hale Nani Lanikai invites you to experience authentic island living in a refined, serene setting....
From $513/night
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...
From $340/night
Welcome to the monthly rental Penthouse in Lanikai! We have been sharing our piece of paradise for over 20 years.! Everyone deserves to experience...
From $1,176/night
This Kailua beachside haven is a newly remodeled luxury home just one block from beautiful Kailua Beach on Oahu's Windward Coast. Completely...
From $155/night
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east...
From $342/night
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 is a stylish 5-bedroom vacation rental just steps from the powdery sands of Lanikai Beach, offering a perfect blend of luxury and...
From $227/night
Nestled in the beachside community of Lanikai, Kailua, this fully furnished home is over 1400 square feet of island style living. Beautifully yet...
From $640/night
A serene haven where heaven meets the ocean. This elegant and contemporary home boasts 2 bedrooms and 2 bathrooms. Immerse yourself in the beauty of...
From $724/night
Our beautiful home has been featured in Hawaii Home Magazine and has received a best in class award from the Hawaii Builders Association. The home is...
From $265/night
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 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 $1,187/night
Kai Hale is a luxurious oceanfront vacation home in Lanikai, perfectly positioned for stunning views of the Mokulua Islands. Designed for effortless...
From $4,804/night
The Kailua Beach Historic Cottage is a beautifully renovated 1937 plantation-style beach house just steps from world-renowned Kailua Beach. Blending...
From $383/night
”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
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 $3,221/night
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 $169/night
We're situated in a prime residential neighborhood, just 2 blocks away from Kailua Beach Park Entrance and Kalapawai Market, as well as downtown...
From $399/night
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 $688/night
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an...
From $774/night
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 $1,460/night
This oceanfront Lanikai Beach vacation home is a serene 4-bedroom, 3-bath retreat located directly at the beginning of world-famous Lanikai Beach....
From $4,254/night
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
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
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
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
Set along Kailuana Loop on Oahu’s beautiful windward coastline, Hale Ohana by Gather offers a spacious, family-friendly retreat designed for easy...
From $937/night
Lanikai Seashore is a stunning beachfront sanctuary in Kailua, HI, where you can experience the vivid beauty of Lanikai Beach just beyond your...
From $1,021/night
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 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 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 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 $1,890/night
Hale Mokulua is perfectly situated in front of the iconic Mokulua Islands. Relax as you watch the sun and moon rise over the turquoise water. Lounge...
From $220/night
Just a two minute (75 yard) walk to beautiful Kailua Beach using our private beach access! Air conditioning and Wifi included. This lovely...
From $191/night
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
Attractive, ground floor, 2 bedroom 1 bathroom unit with a separate living room and private entry. Located on the island of O’ahu, you'll find...
From $231/night
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 $140/night
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 $1,176/night
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 $211/night
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 $450/night
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 $629/night
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 $2,460/night
Hale Kolea is a spacious 3-story hillside retreat at the end of Lanikai, perfect for families or groups seeking ocean views, privacy, and direct...
From $2,593/night
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
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 $400/night
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 $1,080/night
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 $216/night
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
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 $282/night
At Old Hawaii Beach House and Guest Cottage in Lanikai, we extend to all our guests the old-fashioned Hawaiian Hospitality, and the famous Spirit of...
From $409/night
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 $240/night
Large Studio with roomy bathroom beside a quiet home. Enjoy your coffee on your own patio near the pool overlooking the canal where you can kayak or...
From $169/night
Welcome to our newly renovated 1-bedroom apartment in Kailua, Oahu. This rental offers everything you need for a comfortable stay, providing a...
From $1,092/night
Escape to Hale Aloha by Gather, a serene four-bedroom, two-bathroom waterfront retreat nestled at the end of a peaceful Kailua cul-de-sac. This...
From $1,798/night
This Kailua Beachfront Home is a relaxed oceanfront retreat offering panoramic views of Kailua Bay and the Ko'olau Mountains. Located just minutes...
From $357/night
Only a 5 min Walk to Lanikai beach!! No pets firm. As of 7/2022 new high speed Wi-Fi! Welcome to the Viewhouse in Lanikai! We have owned this home...
From $1,463/night
Inquire about short stays, we accommodate them where possible. Spacious, resort-style residence located within 100 yards of Kailua Beach. Featuring a...
From $2,793/night
Palione Papalani - meaning "Heavenly Sands" - is a newly renovated 6-bedroom luxury vacation rental just steps from Kailua Beach, offering the...
From $298/night
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This large...
From $267/night
Picture yourself in paradise. Our beautiful, clean, beach style rental is situated under a plumeria tree and is available for your relaxing stay in...
From $444/night
Discover your private island retreat at Charming Cottage in Lanikai by Gather, a beautifully renovated 1-bedroom, 1-bath home surrounded by lush...
From $239/night
This is a legally established property, please read more below....Enjoy our Hawaiian sunshine and one of the most beatuiful beaches in the world. Our...
From $2,221/night
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
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
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 $150/night
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 $1,091/night
Enjoy sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand. This beautifully decorated 3 bedroom...
From $461/night
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 $549/night
Kailua Absolutely Oceanfront Deluxe Legal Vacation RentalThe closest house to the Ocean in KailuaLocated in a quiet upscale neighborhood away from...
From $499/night
Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply.A two-bedroom, one-bath,...
From $670/night
To comply with Honolulu vacation rental rules, we only rent once in a 30-day period. You may inquire about a shorter stay if our calendar is open for...
From $210/night
The City and County rules only allows 30 day or longer rentals, Contact us for more information or check our calendar. Hale Kai - You won't find a...
From $2,410/night
Additional guest fee of $98 per person per day applies to parties over 10 people. Additional service fee and tax will apply.A private home with eight...
From $165/night
vrKCV - Kona Makai 6204, Professionally Managed by Kona Coast Vacations.Experience Oceanfront Living at Kona MakaiNestled along the lava rock shores...
From $3,011/night
Following Oahu laws a 30 minimum lease required for any rental. Please inquire about it.Right on renowned Kailua beach, our beachfront villa equipped...
From $129/night
Cute one bedroom beach side apartment with peak-a-boo ocean view in perfect location, on Ali'i Drive across the street from Turtle Beach. We are...
From $700/night
This Kailua beach estate is a 3-bedroom vacation home on over an acre of land, just one house back from world-famous Kailua Beach. Offering 2,200...
From $295/night
Hawaii's Hidden Hideaway is an AWARD-WINNING Bed and Breakfast. Recipient for two years in a row the MOST ROMANTIC HIDEAWAY AWARD, voted by its...
From $137/night
Enjoy your Hawaiian vacation in one of Kona's most popular complexes. Casa is very well maintained with beautiful gardens and an awesome ocean-front...
From $105/night
Aloha Kakou! Thank you for checking out my unit near the beach. I have a kitchen to test out your cooking skills and a balcony overlooking the pool...
From $625/night
Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by...
From $112/night
vrKCV - Sea Village 2102, Professionally Managed by Kona Coast VacationsOcean View Ground Floor Kona Condo | Walk to Honl'sOcean views, sunset skies,...
From $372/night
Min 30 days requiredLush tropical gardens make this private home into a quiet, comfortable retreat. Large enough for six adults, plus a couple of...
From $293/night
TOTALLY REMODELED COMPLETED January 2025!!* New Italian ceramic tile floors & showers.* Solid Bamboo Cabinetry throughout. * Complete new bathrooms...
From $1,180/night
Let the serene energy of Maluhia draw you into effortless island living. Nestled in the heart of Kailua, Oahu, this two-level private villa blends...
From $122/night
Aloha, a small 400 sq ft studio condo unit is centrally located at the beautiful Kona Islander Inn off Ali'i Drive and Kaukini Highway. Just a few...
From $166/night
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an...
From $295/night
We live onsite and the house was built as a rental in mind. When facing the building from the street, we are on the left side. You have your own...
From $447/night
Just steps from the white sand shoreline of Kailua Beach, Ranch Beach House offers a private, garden-surrounded setting designed for relaxed island...