Find 5 Star Hotels in Kailua, HI

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Check availability on Kailua 5 Star Hotels

Compare Kailua 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
Exterior

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

9.2 out of 10, Wonderful, (72)
"Was excellent "
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
PRIVATE BEACHFRONT RENTAL
1 bedroom, iron/ironing board, WiFi, bed sheets

PRIVATE BEACHFRONT RENTAL

10.0 out of 10, Exceptional, (127)
"It is perfect in every way . The host is friendly, helpful and kind. The room is very clean and comfortable. The view and access to the beach is unbeatable. "
PRIVATE BEACHFRONT RENTAL
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
Fridge, microwave, dishwasher, coffee/tea maker

La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)

10.0 out of 10, Exceptional, (6)
"Really enjoyed my stay at La Bella’s serene atmosphere. I felt very welcomed, and Shannon & Gabriel were very helpful what ever the question. Breakfast was heavenly, and every detail in the living space was thought and designed. Definitely coming back !"
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
1 bedroom, desk, iron/ironing board, travel crib

La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)

10.0 out of 10, Exceptional, (2)
"Great Hosts"
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
Centrally located, pet-friendly, 1 bedroom in Kailua
Terrace/patio

Centrally located, pet-friendly, 1 bedroom in Kailua

Centrally located, pet-friendly, 1 bedroom in Kailua
Beautiful Kailua Hale Studio
Microwave, stovetop, coffee/tea maker, toaster

Beautiful Kailua Hale Studio

10.0 out of 10, Exceptional, (54)
"This property provided everything we needed. The location was great as it was just a short walk or bike ride to either the beach or town. The bikes were provided by the owners as well as beach chairs, coolers etc. The owners were awesome and communicated check in, amenities, nearby restaurants, beaches, stores and everything we needed clearly and made for an easy, enjoyable stay. We will be back and we highly recommend."
Beautiful Kailua Hale Studio
Lovely Private Kailua Cottage
Fridge, microwave, stovetop, coffee/tea maker

Lovely Private Kailua Cottage

10.0 out of 10, Exceptional, (21)
"The cottage was very comfortable and convenient for our stay in Kailua. Many thanks to Tobi and Yvonne for their great hospitality! They thought of everything to make our stay as comfortable as possible. We definitely want to stay again on our next visit to Kailua. 🌺"
Lovely Private Kailua Cottage
DaLight - A beautiful home in a quiet neighborhood
Fridge, microwave, coffee/tea maker, toaster

DaLight - A beautiful home in a quiet neighborhood

9.0 out of 10, Wonderful, (2)
"The house is one of the nicest I have stayed in in Kailua. The room was a little warm at night when I was trying to sleep but Adrien (the home owner) told me they have a plan to fix that."
DaLight - A beautiful home in a quiet neighborhood
Hawaii Sheffield House
1 bedroom, individually decorated, iron/ironing board, free WiFi

Hawaii Sheffield House

2.0 star property
Hawaii Sheffield House
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Learn more about Kailua

Trip time! Discover the island views, beaches, and hiking in Kailua.

See all hotels in Kailua
Kailua Beach which includes a sandy beach, swimming and landscape views

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Kailua?
How much you pay for a 5-star hotel in Kailua depends on things such as when you plan to go and the length of your break. Our top tip for scoring an awesome deal? Use our pricing filters to check out the available hotels for your preferred dates.

  • Search for the lowest price per night

What makes a hotel 5 stars in Kailua?
From gourmet restaurants and fitness centers to pools and deluxe bedding, the 5-star experience in Kailua is all about comfort and indulgence. But it requires more than just upscale conveniences to receive a 5-star rating. Hotels also have to provide superior guest services like in-room massages, on-site dry cleaning and laundry and room service any time night or day.
Are there any 5-star all-inclusive resorts in Kailua?
Use our handy filters to find a luxurious getaway in Kailua where everything you need is included. After your initial search, narrow down your results for accommodations that have a 5-star rating and are categorized as “All inclusive.” The main thing to look forward to at these stays? Relaxation and indulgence.
Are there any 5-star vacation rentals in Kailua?
Although there aren’t any 5-star vacation rentals in Kailua on our site, we have a range of retreats that promise a fantastic getaway. Find one that matches your needs by checking out our vacation rentals in Kailua.