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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Kailua

An Absolute, Perfect Paradise and Affordable
Outdoor dining

An Absolute, Perfect Paradise and Affordable

9.6 out of 10, Exceptional, (160)
"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
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Sun-loungers, beach towels

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

9.4 out of 10, Exceptional, (138)
"We walked to Lanikai Beach to go snorkeling."
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Seaside Paradise
On the beach, sun-loungers, beach towels

Seaside Paradise

9.4 out of 10, Exceptional, (194)
"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, (133)
"Koi Palms has it all—cozy comfort with lovely decor, koi pond just outside the windows with beautiful fish and the calming sound of falling waters, shady parking beside a private gate, quiet and well-tended neighborhood, easy 5-10 walk to both the beach and Kailua town, and, finally, very friendly and helpful owners on site. Grab it if you can!"
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Breathtaking Ocean Views Beach Cottage
On the beach, sun-loungers, beach towels

Breathtaking Ocean Views Beach Cottage

9.4 out of 10, Exceptional, (145)
"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
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, (102)
"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.
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
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
Sunny Hawaii BeachFront Property
On the beach, sun-loungers, beach towels

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 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 thoroughly enjoyed our stay in a lush and tropical yard and cozy cottage.the location was perfect across the street with several beach accesses and a few blocks from lanikai beach.the cottage is nestled in a beautiful neighborhood.our gracious and accommodating host Lynn and her family provided everything we needed we will miss our new friend junee"
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
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, (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
Studio by the ocean. Oceanfront property with WiFi, AC, parking, great location.
Terrace/patio

Studio by the ocean. Oceanfront property with WiFi, AC, parking, great location.

Studio by the ocean. Oceanfront property with WiFi, AC, parking, great location.
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
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.
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
Beautiful Beachside Bungalow
Beach nearby

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
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
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
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
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

OUTRIGGER Reef Waikiki Beach Resort

OUTRIGGER Reef Waikiki Beach Resort

10/10 Excellent
"Very nice,restaurant is very nice for all meals! Everyone pleasant and helpful! Will come back!"
Stephen 7-night trip
Posted 16 hours ago
OUTRIGGER Reef Waikiki Beach Resort