Search Cottages in Kailua

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Kailua

An Absolute, Perfect Paradise and Affordable
Outdoor dining

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
On the beach, sun loungers, beach towels

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
On the beach, sun loungers, beach towels

Seaside Paradise

9.4 out of 10, Exceptional, (189)
"The stay was everything we imagined and then some."
Seaside Paradise
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Beach nearby, sun loungers, beach towels

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#90/BB -0013
Sun loungers, beach towels

Less than 1 min walk to Kailua Beach- NUC#90/BB -0013

9.4 out of 10, Exceptional, (134)
"We walked to Lanikai Beach to go snorkeling."
Less than 1 min walk to Kailua Beach- NUC#90/BB -0013
Sunny Hawaii BeachFront Property
On the beach, sun loungers, beach towels

Sunny Hawaii BeachFront Property

8.8 out of 10, Excellent, (6)
"From the minute we stepped into the beach house we were impressed by how clean it was! The view is beautiful for sunrise and sunsets! Plenty of sandy beach and everything you could need to enjoy your time outdoors! Timely communication and just an overall wonderful experience!"
Sunny Hawaii BeachFront Property
Newly-upgraded home with Diamond Head views - walk to Waikiki Beach
Property grounds

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
Beach

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

3.0 star property
9.8 out of 10, Exceptional, (77)
"We enjoyed the accommodations. Everything worked out well. Friendly owners and visitations from the family dog were appreciated"
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Charming Lanikai Cottage. Close to beach, A/C, parking.
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (101)
"It was the perfect quaint cottage for my husband and me in the perfect quiet location that was a quick 5 minute walk to Lanikai Beach and easy access to everything all over the island. It was a half mile walk to the pillbox hike. We will stay there again. "
Charming Lanikai Cottage. Close to beach, A/C, parking.
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
Beach nearby, sun loungers, beach towels

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
Smart TV

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
Sun loungers, beach towels

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
Beach nearby

Beautiful Beachside Bungalow

10.0 out of 10, Exceptional, (13)
"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
Sun loungers, beach towels

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
Property grounds

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
Exterior detail

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
Property grounds

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
On the beach, beach towels

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
Sun loungers

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
Outdoor dining

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Kailua with Expedia?
Expedia has some great cottages in Kailua, so start packing your bags for a memorable vacay 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.