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.
Kakela Kai, Beachfront Kailua Home, Private, A/C
A comfortable beachfront home set in a security-gated neighborhood with central air condition. Decorated with island style rattan furnishings, ceiling fans throughout the house, cool white tile, granite counters and wooden flooring. There is a well stocked kitchen with...
The Pool House: 6 BR Kailua Home with Pool, Walking Distance to Kailua and Lanikai
The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's Steakhouse. The home offers a...
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to 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.Hale Ohana meaning Family House is just that!...
Walker's Lanikai Beach House – Historic Oceanfront Retreat
This property is professionally-managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1757. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
This Kailua, beachside, pool (heated) home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!Each room has an individually controlled AC system. The...
Gorgeous Lanikai Villa with Access to Secluded White Sand Beach
This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches...
Kai Hale: 3 BR Oceanfront Lanikai Beach Estate
AlohaRelax and unwind at Kai Hale. This beautiful Lanikai ocean front home is directly in front of the Mokulua Islands.This location is suited for year round living and is ideal for stand-up paddling, kayaking, boogie boarding, snorkeling, and children's activities. A...
Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach
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 house from the white sands of Kailua beach (Private beach gate is located adjacent to our property and the house is less...
Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms
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 - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and...
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
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.Welcome to Hale Nani Lanikai by Gather, a...
3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!
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 here.Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of Oahu....
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...
Charming Dolphin Suite with AC in delightful Kailua
Consider this studio your home away from home while you visit Kailua. We hope you enjoy what our place and Kailua has to offer.NOTE: Temporary construction site is nearby so price has been reduced. Details provided upon booking request so you can make a decision if this...
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
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 the beach, a beautiful garden to enjoy, great host family and close to amenities. Our luxury bedding and upgraded style...
Happy House on Exquisite Kailua Beachside Property!
Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by stone walls with palms, banana trees and beautiful tropical gardens. Very safe and fun for kids, great for families,...
Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.
Welcome to the monthly rental Penthouse in Lanikai! We have been sharing our piece of paradise for over 20 years.! Everyone deserves to experience the Hawaiian lifestyle! Sunrises, moonrises, walks, bike rides, and daily runs on the beach. We have guests from all over...
Place in Paradise - Kailua Beach Oceanfront Vacation Home
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1802 It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
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 is the perfect blend of island and modern living. Our guest house has a master bedroom (king bed) with an en suite...
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
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 private lane. Ocean, park and Mountain view’s are captured from the rooftop sun deck. The Set Up:Cozy and efficient...
Lanikai Breeze – Contemporary Comfort Steps from the Shore
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.Just steps away from coveted Lanikai Beach,...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...
Beachside Kailua AC 3min walk to beach! Inquire for available dates!
THIS PROPERTY IS A LEGAL SHORT TERM RENTALCONTACT HOST/RESERVATIONS & DETAILSThis airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Remodeled kitchen and bath(s) finish off this stunning home....
Oceanfront Lanikai Beach Vacation Home
TA-006-302-3104-01Beautiful ocean front home at the beginning of Oahu's famous Lanikai Beach!. 2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking views, a brand new courtyard pool with privacy and manicured yard space, a...
Kailua Beach Historic Renovated Cottage
This property is offered as a monthly rental. Although full-month occupancy isnot required, the monthly rate remains fixed and applies in full, regardlessof the number of nights stayed, as prorated rates are not available.One of the original homes on Kailua Beach, this...
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
HALE LANIKAILic# TA-161-257-7280-01Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.Hale Lanikai is BACK! Better than ever!!All new furnishings throughout the property.Original Koa...
Mokulua Sunrise Ocean Villa Lanikai
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.Enjoy top-tier luxurious living on your next...
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
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 unparalleled experience of luxury and relaxation. Comprised of two separate structures- one newly built in 2018, along...
Luxury beachfront villa on a world class beach in Kailua, HI
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 Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises...
Lanikai Cottage: Charming Tropical Oasis with Private Pool
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.Charming Lanikai Cottage features two...
Orchid House - Pool and Endless Ocean Views!
ORCHID HOUSETA # 087-311-0016-01With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors, granite countertops, slate stone...
Kailua Beachfront Vacation Home with Pool
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1783. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Bright and airy 1-bedroom cottage in charming Kailua, 1 block to beach. WiFi, AC
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 has to offer, including sandy beaches, popular restaurants and eateries, all kinds of great boutique shops, Whole Foods,...
Lokomaika'i Kailua: Elegant Vacation Home with Pool & AC
On Oahu’s sun-kissed Windward side, Lokomaika’i Kailua (meaning “Gracious Kailua”) invites you to slow down, open the sliding glass walls, and let the island breeze transform everyday living into something magical. This single-level home blends open-concept...
Naupaka Hale - Lanikai Beach Home & Cottage
NAUPAKA HALETA-151-566-1312-02THIS PROPERTY RENTS ONLY MONTHLY FOR 30 DAYS AND LONGER.Idyllic classic Hawaiian style vacation rental home on large lot with huge sandy beach right in front of your very eyes. This beautiful vacation rental home offers breathtaking views...
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
Indulge in an Unforgettable Stay at Our BRAND-NEW Luxury Beach House at Kailua BeachEscape to our newly built, luxurious rental home, perfectly nestled in the heart of the most sought-after location by the world-renowned Kailua Beach. This contemporary haven is designed...
Family friendly Quiet Kailua Beachside lane, steps to lane private beach access
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; laundry, 1 bedroom and bath on 1st floor. Washer/Dryer, Basic Cable, and Wifi includded. Small pets ok. Monthly rentals only -...
Just 40 Steps to the Most Beautiful White Sand Beach in the World
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 overlooks the beautiful beach, Kailua Bay, and Offshore Islands.Kailua is a small upscale town with excellent retail stores....
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
Just steps from the sands of Lanikai Beach, Villa Hui Hou blends resort-style outdoor living with the comforts of a private luxury home. This five-bedroom, four-and-a-half-bath retreat offers 4,920 square feet of space designed for gathering, relaxing, and making...
Hale Mokulua: Lanikai Multi-Home Estate - Sleeps 14
With 3 separate living spaces, this remodeled Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern kitchen and a wonderful,...
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...
Hale Lani – Heavenly Lanikai Hillside Luxury
Perched on the northern shores of Oahu in Lanikai, Hale Lani lives up to its name as a true "house in the heavens." This hillside retreat blends sweeping ocean views, open-air design, and effortless island living into a one-of-a-kind vacation home. With 3 bedrooms, 4...
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....
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 90 day minimum short term rental laws, we may not advertise to rent for a period shorter than 90 days."Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully furnished with a modern meets the...
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...