Kailua Beach Vacation Rentals
Kailua Beach vacation rentals place you steps from one of Oahu's most scenic shorelines. Located on the Windward Coast, Kailua offers soft white sand, turquoise water, and a laid-back local vibe. From beachfront cottages to spacious family homes, these rentals are perfect for travelers seeking comfort, beach access, and a true Hawaiian escape.
Nestled along the eastern coast of Oahu, Kailua Beach is known for its gentle waves, powdery sand, and views of the offshore islets Popoia and Mokulua. Our collection of Kailua vacation rentals includes charming beach cottages, 1-bedroom bungalows, and spacious family estates with private yards and lanais.
Just minutes from your rental, enjoy beach walks, kayaking, and sunrise paddleboarding. The nearby Lanikai Beach and Kailua Beach Park are both top-rated and within walking distance. Stroll to Kailua Town for local shops, cafés, and organic markets, or bike along scenic coastal paths.
Key Features of Kailua Beach Rentals
- Beachfront or short-walk homes with ocean access
- 1 to 5+ bedroom layouts ideal for couples or families
- Private lanais, BBQs, enclosed yards, or outdoor showers
- Pet-friendly and kid-friendly options available
- Walkable to Kailua Town and dining options
- Calm swimming waters and sunrise views
Looking for more Oahu options? Browse Honolulu rentals or Diamond Head escapes. For even more privacy, explore our bungalow and private estate selections.
Steps from Kailua Beach, heated pool, gazebo, AC, NO CLEANING FEE!
This stylish, designer decorated, 4 bed, 4 Bath home is just across the street from Kailua Beach. We call her Coastal Soul. Lounge in the beach chic living room, cook in the gourmet, fully equipped kitchen, or swim in the heated lagoon pool. With a gazebo, the private...
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...
Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views
Recently updated with stylish contemporary design, this spacious Kailua home sits on Kailua Beach with nearly 100 linear feet of beach frontage. The home features direct and private access to the white sands with over 2 miles of beach walking at your front doorstep. 6...
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,...
Place in Paradise - Kailua Beach Oceanfront Vacation Home
Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half baths make this an ideal home...
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...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This spectacular beachfront home offers two living spaces on the best part of Kailua Beach - known throughout the State as one of the most pristine white sand beaches - the perfect beach home for accommodating groups large and small. Both the main house (5 bedrooms) and...
Kailua Beachfront Vacation Home with Pool
One of the few Licensed Short-Term Vacation Rentals on the Windward side of Oahu, this three bedroom, three bath home with large swimming pool sits on .9 acres of Kailua Beachfront. The home has been recently refurbished with new furnishings, fixtures, appliances, linen...
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 -...
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...
'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...
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...
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...
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...
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...
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...
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...
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...
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...
Luxury Beach Vacation House in Kailua Beach
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 bedrooms on Kailua Beach (Voted Number One Beach in America). (Adjacent 2-bedroom Guest Cottage also available to...
Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Laundry
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This is a fully furnished & renovated/updated 3/2 rental with a big, fenced & shady yard with tropical trees and plants, including...
Luxurious, Private Hilltop Retreat with Postcard View -- minutes to Kailua Beach
With views like these, you may never want to leave!This top level of a 3 story executive home has its own entry driveway and private parking areaWith no homes behind it, the property’s location gives you one of the best views in the islands — providing an ideal...
Private Hilltop Retreat, Spectacular View, Minutes to Kailua Beaches!
This 2 bedroom, 2 bath private downstairs level of a 3 bedroom executive house has views of Kaneohe bay and is in an ideal location between Kaneohe and Kailua, just minutes from Kailua town and its beaches. First bedroom, which opens onto the cabana deck, has a queen...
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/C
Just four homes away from the Kailua Beach pristine white sands, this spacious retreat combines a stunning 4-bedroom home with a separate private studio cottage. Your perfect Hawaiian getaway awaits with a thoughtful blend of comfort and island living. Sleep in...
Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore
Welcome to Kailua Beach Villa, a spacious and contemporary oceanfront retreat on Oʻahu’s Eastern Shore. With 5 bedrooms, 5 baths, and 4,000 square feet of airy living space, this private villa blends modern design with barefoot luxury. Step outside to direct beach...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
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.Stay at Kailua Beachside by Gather, a...
Loft In Kailua - Spacious with Parking, Internet and minutes to Kailua Beach!
MINUTES TO KAILUA BEACH AND TOWN!!This well appointed one bedroom split level loft apartment is beautifully furnished with high ceilings and open floor plan. The upstairs has a shuttered master suite with queen bed, a huge en-suite full bath that has a soaking tub and...
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from 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.Seahorse Beach House is a hidden Hawaiian gem,...
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
Live the beach life! An opportunity to live across the street from Kailua Beach Park, with the perfect combination of sandy beach, large grassy areas, tall ironwood trees, and turquoise-blue waters. You will love this generous ground-level one-bedroom, one-bathroom...
Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
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 Kailua Beach House by Gather, a...
Kailua Beach Bop
Discover Kailua's island charm while staying in our Hawaiian style home. Wake up to chirping birds on a quiet treelined street. Enjoy your breakfast in the sun room overlooking the lush green backyard filled with fruit trees. The living spaces are open & flooded w/...