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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Kailua and around

An Absolute, Perfect Paradise and Affordable
Situated on a sandy beach, this beachfront hotel offers stunning ocean views.

An Absolute, Perfect Paradise and Affordable

9.6 out of 10, Exceptional, (159)
"Stay was simply wonderful! Turtles galore and Terries property is the sweetest of all the cottages! Terries sweet all day long as well. Seriously this stay will make you come back for more. "
An Absolute, Perfect Paradise and Affordable
Breathtaking Ocean Views Beach Cottage
Situated near the coast, this building offers a serene natural setting with lush greenery and palm trees.

Breathtaking Ocean Views Beach Cottage

9.4 out of 10, Exceptional, (142)
"We loved our stay here. You really are right on the beach; I was wondering if the pictures would be accurate but the beach is even BETTER than pictured. A magical time for our family. Book it!"
Breathtaking Ocean Views Beach Cottage
Seaside Paradise
Enjoy a serene ocean view from this outdoor space surrounded by lush greenery and a low hedge.

Seaside Paradise

9.4 out of 10, Exceptional, (193)
"The stay was everything we imagined and then some."
Seaside Paradise
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Enjoy a peaceful beach experience with access to the ocean.

Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

10.0 out of 10, Exceptional, (132)
"The comfortable, stylish, and nicely equipped space host Tricia has created at Koi Palms is an ideal base for a couple to explore the multiple pleasures of Kailua and Oahu, with easy, quick access to some of the planet's most gorgeous beaches. Highly recommend."
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Enjoy a serene beach experience with clear waters and a wide, open shore.

Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760

9.4 out of 10, Exceptional, (135)
"We walked to Lanikai Beach to go snorkeling."
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Sunny Hawaii BeachFront Property
Situated on a sandy area, this two-story building offers a balcony with a clear view of the surrounding area.

Sunny Hawaii BeachFront Property

8.8 out of 10, Excellent, (6)
"Easy check in, accurate listing, location on beach was beautiful. I wasn’t expecting no a/c but a quick Google search deemed it common for the island. There was also a play set on property which was an awesome surprise! "
Sunny Hawaii BeachFront Property
Newly-upgraded home with Diamond Head views - walk to Waikiki Beach
Surrounded by lush tropical vegetation, this home offers a serene retreat with a porch and a charming entrance.

Newly-upgraded home with Diamond Head views - walk to Waikiki Beach

9.2 out of 10, Wonderful, (20)
"Loved the cottage..basic but all the essentials. The location is fantastic. We would definitely use again"
Newly-upgraded home with Diamond Head views - walk to Waikiki Beach
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Enjoy a tranquil beach experience with breathtaking views of the surrounding mountains and calm sea.

Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage

3.0 star property
9.8 out of 10, Exceptional, (77)
"Absolutely incredible, couldn’t have asked for a more perfect place to experience the beauty of Kailua & Lanikai. Highly recommend and plan on coming back in the future!"
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Charming Lanikai Cottage. Close to beach, A/C, parking.
Escape to a tranquil coastal haven surrounded by lush greenery and serene waters.

Charming Lanikai Cottage. Close to beach, A/C, parking.

10.0 out of 10, Exceptional, (101)
"Very well-appointed cottage, everything was wonderful. Kate is very easy to communicate with, and the location was perfect. Short walk to the most beautiful beach. Chairs and cooler made our day perfect. Very close to town, just a short drive. Highly recommend."
Charming Lanikai Cottage. Close to beach, A/C, parking.
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
Relax on the deck surrounded by lush greenery and potted plants, with a pergola overhead.

Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.

9.8 out of 10, Exceptional, (74)
"My husband and son and I spent five lovely days in Noni's cozy cottage. We loved the walks to the pristine beaches, the view from the lanai while we ate breakfast, and the trips to explore other sights on the island. I have recommended this property to friends and I hope we can enjoy Noni's hospitality in the future. "
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
Kaikea Modern 1Ba Lanikai Cottage: Stylish & Private - 5 Min from Lanikai Beach
Surrounded by lush greenery, this two-story house offers a serene retreat with a driveway and garage.

Kaikea Modern 1Ba Lanikai Cottage: Stylish & Private - 5 Min from Lanikai Beach

10.0 out of 10, Exceptional, (2)
"This property is the best rental we've stayed at by far! Super clean, 3 minutes walk to the best beach in Oahu, Lanikai and just so charming. My husband and I celebrated our honeymoon here and we couldnt ask for a better location. The host was very nice and accomodating. I recomend this property 100%. Thank you for helping make our first visit to Hawaii the most memorable one :) "
Kaikea Modern 1Ba Lanikai Cottage: Stylish & Private - 5 Min from Lanikai Beach
Footsteps to Hawaii's Best Beach
Relax in a serene outdoor space surrounded by lush greenery and comfortable seating.

Footsteps to Hawaii's Best Beach

10.0 out of 10, Exceptional, (45)
"Great area walking distance to beach and town for shopping. Great host and family."
Footsteps to Hawaii's Best Beach
Beautiful Beachside Bungalow
Escape to a tranquil beach scene with turquoise waters and a majestic palm tree.

Beautiful Beachside Bungalow

10.0 out of 10, Exceptional, (14)
"We love Kailua and Vicki’s cottage is a gem of a place. The location can’t be beat and it has all that is needed for a stay. Hope to come back again. Thanks Vicki!"
Beautiful Beachside Bungalow
Footsteps to Hawaii's Best Beach
Relax on the porch with comfortable seating and enjoy the serene surroundings.

Footsteps to Hawaii's Best Beach

10.0 out of 10, Exceptional, (55)
"Great location to everything Hawaii. Quiet and felt like home away from home. They had everything we needed for a comfortable long term stay."
Footsteps to Hawaii's Best Beach
Ocean View Cottage with Separate Suite
Enjoy the serene views from this balcony overlooking lush green surroundings.

Ocean View Cottage with Separate Suite

10.0 out of 10, Exceptional, (54)
"We had a very enjoyable time and were very happy with our stay!!"
Ocean View Cottage with Separate Suite
Charming cottage close to everything - walk to beach, zoo, & park
Stunning garden surrounds this traditional home with a pathway leading to the front door.

Charming cottage close to everything - walk to beach, zoo, & park

9.0 out of 10, Wonderful, (12)
"The cottage is in the most convenient location with beautiful view of Diamond Head from bedrooms. Walking distance to great food, cross Kapiolani Park to beach in 15 mins. It was spotless! Only minor downside was drains were slow and would back up in kitchen and bathroom, likely because of older plumbing. We would love to stay here again."
Charming cottage close to everything - walk to beach, zoo, & park
One Bedroom Cottage with kitchenette and private garden
Stroll through lush gardens featuring tropical plants and palm trees, surrounded by a tranquil outdoor space.

One Bedroom Cottage with kitchenette and private garden

2.0 star property
One Bedroom Cottage with kitchenette and private garden
Laie Cottage by the Sea - Striving for an Eco-Friendly & Sustainable Home
Relax on the wide sandy shores and enjoy the gentle waves in this serene beach setting.

Laie Cottage by the Sea - Striving for an Eco-Friendly & Sustainable Home

Laie Cottage by the Sea - Striving for an Eco-Friendly & Sustainable Home
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Enjoy the tranquil beach scene with a shaded area, wide beach, and clear waters.

Kailua Palms Guest House with Pool and Views! Parking and wi-fi included

9.6 out of 10, Exceptional, (13)
"What a special property! We had the best time at this gorgeous cottage. We loved how it opens up to the beautiful tropical yard. The pool is wonderful and the sunrises are fabulous out the bedroom window. The owner is a joy to work with…so responsive to everything we needed! We will definitely be back!"
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Life on the Water Hawaii with WiFi & AC & Washer/Dryer
Enjoy a serene view of the water from this outdoor deck, perfect for dining or relaxation.

Life on the Water Hawaii with WiFi & AC & Washer/Dryer

Life on the Water Hawaii with WiFi & AC & Washer/Dryer
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kailua Hotel Reviews

Holiday Inn Express Waikiki by IHG

Holiday Inn Express Waikiki by IHG

10/10 Excellent
"Great value and perfect location"
Norman 3-night trip
Posted 6 hours ago
Holiday Inn Express Waikiki by IHG

Frequently asked questions

Are there any family-friendly cottages in Kailua?
Yes, there certainly are! Book a room at Newly Renovated Lanikai, Steps To Ocean A, a great base for uncovering the great outdoors in Kailua. This family-friendly cottage has a 3-star rating and offers useful amenities like a barbecue grill and clothes washing facilities. Kailua boasts loads of family-friendly attractions to check out that'll entertain the kids. Lanikai Beach and Kailua Beach promise a fun-fuelled day for all ages.
Why book your cottage in Kailua with Expedia?
Expedia has some great cottages in Kailua, so start packing your bags for a memorable holiday close to nature. If you have a certain budget, select how much you're willing to spend and the preferred star rating of your property. Or take advantage of our filters to search for cottages with a hot tub or free WiFi. We'll help you find a suitable place whatever your trip looks like.
How can I find cheap cottages in Kailua?
With Expedia's helpful filter tool, booking cheap cottages in Kailua is a cinch. To discover stays that'll make your wallet smile, tailor your search results by star rating, budget and amenities.