Kailua Vacation Rentals – Beachfront Homes and Island Cottages
Kailua vacation rentals deliver an authentic island experience on Oahu's scenic windward coast. Stay steps from world-famous beaches like Kailua Beach and Lanikai, with cozy cottages, modern family homes, and tropical escapes perfect for kayaking, hiking, and relaxing in paradise.
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 perfect for remote work or extended stays
- Local eateries, cafés, and groceries within walking distance
Perfect 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 discover why travelers return to this corner of Oahu year after year.
Steps To Kailua Beach
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 within a 2 minute walk to Kailua Beach Park, the Kalapawai Market and Buzz's Steak house. There is ocean, mountain and...
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Discover the allure of Kailua at Villa Hui Hou...
Available and legal for stays less than 30 days.
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 unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.The Hawaii Sheffield House...
Coconut Grove Kailua Vacation Home
This adorable pup-friendly, 3 bedroom, 1 bath vacation rental is ideally located, walking/biking distance to both the quaint shops and eateries of Kailua Town and renowned Kailua Beach! Fill your days with walks on the beach, surfing, SUP or kayak to the islands in...
Hale Lani – Heavenly Lanikai Hillside Luxury
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Find your next dream vacation here at Hale...
Lovely Private Kailua Cottage
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 on a beautifully landscaped property which will lead you to a lusciously landscaped garden with outdoor dining & BBQ....
Enchanting Beach Bungalow with Private Garden
Aloha! We renovated this old-style Hawaiian home so that it will have the charm of old Hawaii with modern conveniences.It is a great retreat for a maximum of 2 easy-going, nonsmoking adults (25 years and older only). This garden oasis (we've planted over 3,000 trees and...
Kailua Condo / Townhouse on Oahu 7 day per 30 day period
”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 physically occupy a rental property for any minimum length of time. Remodeled 2x bedroom 2x bathroom condo / townhouse....
Lanikai Ocean Front Duplex Bungalow Private ocean steps. Contact for rates/avail
Location Location Location! Our Lanikai ocean front location exactly in front of the twin Mokulua Islands provides endless hours of outstanding views from the ocean front yard, the living room, dining room, and side deck. A perfect place to work remotely, as you have an...
Kailua Oceanfront Villa with Heated Pool & Spa - availability Sept, Oct & Nov
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, where you can soak up the sun and relax and end a day of hiking or golf with a massage in the oceanside hot tub. Stay...
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
Charming beachfront cottage right on Kailua Beach! licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage. This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room....
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
"In order to comply with Oahu's 30 day minimum short term rental laws, we may not advertise to rent for a period shorter than 30 days."Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully furnished with a modern meets the...
Paradise On the Hill
Located in Kailua on Kalaheo Hillside on a nice quiet street. This is a fully renovated property with beautiful fixtures and air conditioning. Luxury linen and towels provided. Couch and love seat are recliners for maximum relaxation and comfort. The home is open...
Kailua Beach Hideaway TA-189-305-8560-01
Beachfront! The White Sand of Kailua Beach at Your Door!This 4 bedroom, 4 bath, en suite home is the Perfect Tropical Haven.Tucked away and private, this home embodies the true island lifestyle.Walk or jog the long stretch of beach or lounge by the pool, with...
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
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! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 minutes to the beach, and a short...
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
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 Kailua. The owners live on the property in the main house.The cottage is a 600 square foot 1 bedroom unit. The kitchen is...
Romantic Oceanview Guesthouse. Steps from the Beach!
Just a two minute (75 yard) walk to beautiful Kailua Beach using our private beach access! Air conditioning and Wifi included. This lovely 'hawaiian-style' 700 square foot studio features vaulted ceilings, a large tiled bathroom and a kitchen, as well as beautiful wood...
Peaceful Hawaii Paradise three minutes from Beautiful Beach
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 paddle board to beach. Quiet and clean. We supple you with a start of necessities. Walk to market and excellent...
Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Unwind at Hale Aloha by Gather, your tranquil...
Hale Kolea - Luxury Lanikai Hillside Retreat
Hale Kolea is perfect for families and larger groups... A 3 story home at the end of Lanikai with access to an exclusive secluded beach within a gated drive. This beautiful home is on a hillside overlooking the crystal clear, gorgeous blue and green hued water. Wake up...
Kailua Beach "The Pink House" 100 Yards from Ocean
The Pink House is a perfect beach house set 100 yards from beautiful Kailua Beach. This Hawaiian Style Home has an open floor plan that includes a combination living/dining area with a galley kitchen with stainless steel appliances. Recently added Air Conditioning (we...
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01
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. Kailua Beach is a perfect place to go to 'get-away-from-it-all.' Swim, boogie board, surf, kayak, sail, or windsurf in...
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
This beautiful hillside cottage with stunning ocean view offers the perfect getaway for a couple, small family, or up to four vacationers . Ideal for Military personnel transferring to or from O'ahu who need a month or several months rental. Bedroom has partitioned...
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
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 ID # available upon requestHale Pulelehua “The Butterfly House” has an open spacious Kailua feeling inside and out....
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
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 bedroom with beautiful relaxing living spaces, full kitchen and bathroom. The cottage has a gorgeous private lanai/patio...
Zen Home with AC, Pool, Near Kailua Beach
Inquire about short stays, we accommodate them where possible. Spend your vacation in our Hawaiian style 4 bedroom, 4 bathroom home a 3 minute walk from Kailua Beach. Our home features a balance of indoor and outdoor living. There is a Zen like courtyard and inviting...
Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach
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 extended family. Listen to the waves crashing as you relax on the lanai, or barbeque for your group in true outdoor...
Steps to the Beach Guesthouse
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 common question, yes, we are 'steps' away: 80 medium sized steps for me! The beach is down a sandy path and is a one of the...
Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps
In order to assist you in with your booking, regardless of your travel dates, it is really best to send us a brief message. As such, we apologize in advance and want to be clear that we will not accept any bookings prior to communicating with travelers about your dates...
Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach
Welcome to our newly renovated 1-bedroom apartment in Kailua, Oahu. This rental offers everything you need for a comfortable stay, providing a family-friendly atmosphere that will make you feel right at home.Whether you prefer to barbecue on the covered lanai or take a...
Resort-like, Beach-side Kailua Lanikai, Pool, AC, WiFi, Kayaks, 50% DISCOUNTS
The property marker shows the property location incorrectly. This property is a 2 1/2 to 3 min walk from the sandy beach of Lanikai.Walk through the entry gate, and find yourself in the middle of your own personal "resort". A lush tropical yard greets you as you walk to...
Tradewind Bungalow, in Kailua on Oahu
Attractive, ground floor, 2 bedroom 1 bathroom unit with a separate living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is...
Kahela - Paradise for Rent
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 sand is wide, and there are plenty of trees for shade, so you and the kids can play and relax at the beach all day. This...
*Your Perfect Home * Charming 2BR/2BA Apartment with Full Kitchen, W/D & AC
Take advantage of our Rental in Kailua Oahu, and enjoy a family style atmosphere where you are provided with all of the comforts of home.Whether it be barbecuing under the covered lanai, or taking a walk to award winning Kailua beach, there is something here for...
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!
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 adults or 2 adults + 2 kids comfortably, on a slight uphill to enjoy beautiful Hawaiian scenery, tropical birds and island...
Sweet Vintage Hawaiian Cottage and Guest House! Great deal in beautiful Lanikai!
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 Aloha. Step back in time to the romance, the charm, that is truly 'Old Hawaii.' Tropical plants and flowers (seasonal) in...
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
Island living at its finest, this casual Kailua beachfront home is located on the Windward side of Oahu, 30 minutes from Honolulu and approximately 1 mile from the center of Kailua Town. Enjoy spectacular sunrises over Kailua Bay, the scenic Ko'olau Mountain Range and...
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
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 located in sleepy Kailua Town near Kailua Beach. The two bedrooms are spacious and comfortable. You will like the relaxed...
Huge House, Heated Pool, AC, Steps to Kailua Beach
Inquire about short stays, we accommodate them where possible. Spacious, resort-style residence located within 100 yards of Kailua Beach. Featuring a private courtyard and pool, this indoor/outdoor floor plan is ideal for family gatherings. The extensive renovation...
Tropical Masterpiece in the Heart of Lanikai
Guests to our Well-appointed, Multi-story Home Enjoy a Quiet Location in a Coveted Beach Community. Down Our Private Lane You’ll Find a Large Tropical Lot Hidden Only 400 Feet from World-renowned Lanikai Beach.Three Bedrooms (Master Bedroom King, Second Bedroom Queen...
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living
ABSOLUTELY FABULOUS very large two bedroom two bath house or more.... if you rent the loft which has another HUGE bedroom bath and kitchenette. .Sparkling pool in a private courtyard in the back yard VERY PRIVATE. Asian inspired furniture from a designers eye. ONCE YOU...
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet ok
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This large 700 square foot rental unit called the 'Coconut Corner' is one of the nicest rentals you will find on the Windward side of...
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Charming Cottage in beautiful Lanikai that has been totally renovated in 2021. Everything in the Cottage is new including the furnishings! Short walk to the beach. Enjoy the comforts of home with an efficient kitchen and own washer and dryer. Large lanai to extend the...
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach
Welcome to Palione Papalani – “Heavenly Sands”Just steps from world-famous Kailua Beach, this newly renovated 6-bedroom tropical estate offers the privacy, comfort, and amenities of a high-end resort — all to yourself. ?? Why You’ll Love It:Exclusive Location:...
Heavenly Hale Best Licensed Vacation rental - walk to beach!
Garage. Recently renovated and beautifully, tastefully furnished. Light & Bright. Full kitchen with high end appliances, Ohia hardwood floors, breathtaking views from every window. No pets firm. Living room, TV room, large kitchen, table, outdoor dining room, wrap...
Ocean View Guest Cottage - 1990/NUC-1797
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, ocean view cottage located a few steps from Kailua Beach... Voted Number One beach in America! There are 2 shopping...
Paradise Under the Plumeria Tree
Picture yourself in paradise. Our beautiful, clean, beach style rental is situated under a plumeria tree and is available for your relaxing stay in Kailua. We have taken great care in the design and high quality furnishings of our rental. We live on premises and are...
Fantastic Beach Front Villa
Following Oahu laws a 30 minimum lease required for any rental. Please inquire about it.Right on renowned Kailua beach, our beachfront villa equipped with a pool and jacuzzi is perfect for all your vacation needs. Wake up and go watch the sunrise or a morning jog. The...
Absolutely Oceanfront - 60' Waterfall Lap Pool
Kailua Absolutely Oceanfront Deluxe Legal Vacation RentalThe closest house to the Ocean in KailuaLocated in a quiet upscale neighborhood away from the crowdsHear the waves breaking just outsideGo tide pooling steps away60ft salt-sanitized waterfall lap poolDramatic...
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families
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 a full 30 days.Please request dates that you would like to book, and we will reply.Warmest Aloha ........You have found...