A beach with clear turquoise water, a sandy shore, and several boats lined up on the right.

Kailua Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Kailua vacation rentals

1. Luxurious five-bedroom modern retreat

Enchanted Lake

Wytske K.

AED 9,145 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a large window offering a view of the city skyline and a body of water.

2. Bishop Suites Downtown Honolulu

Downtown Honolulu

Aftan

AED 835 total

includes taxes & fees

10 Nov - 11 Nov

A hotel room with a bed, a nightstand, a lamp, a balcony with a table and chairs, and a city view.

3. Skyline Island Colony Hotel

Waikiki

Iurii

AED 594 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a large flat-screen TV, a sofa, a coffee table, and a view of the ocean through large sliding doors.

4. Aston Waikiki Sunset

Waikiki

Angel

AED 864 total

includes taxes & fees

8 Dec - 9 Dec

A coastal cityscape with a beach, high-rise buildings, and a clear view of the ocean.

5. Partial Ocean View Condo with King or Queen Bed and Parking

Waikiki

Susan

AED 1,775 total

includes taxes & fees

20 Nov - 21 Nov

A beach with clear blue water, a city skyline, and a mountain in the background.

6. Royal Kuhio

Waikiki

Armando

AED 914 total

includes taxes & fees

9 Nov - 10 Nov

A coastal cityscape with high-rise hotels, a beach, and a mountain in the background.

7. Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop

Waikiki

AVenture

AED 1,007 total

includes taxes & fees

6 Dec - 7 Dec

A modern apartment with a balcony, dining area, and kitchen.

8. Regency on Beachwalk Waikiki by OUTRIGGER

Waikiki

Ria Flor

AED 2,669 total

includes taxes & fees

20 Nov - 21 Nov

A modern living room with a glass dining table, white chairs, a grey sofa, and a city view through large windows.

9. Ilikai Marina Vacations

Waikiki

Johnathan

AED 1,312 total

includes taxes & fees

10 Nov - 11 Nov

A cityscape at dusk with illuminated buildings.

10. Charming cozy condo in marvelous Honolulu with WiFi

Waikiki

Mariah H.

AED 882 total

includes taxes & fees

18 Nov - 19 Nov

A nighttime cityscape with a prominent high-rise building reflecting on the water.

11. Modern, renovated studio in Waikiki

Waikiki

Cindy

AED 743 total

includes taxes & fees

13 Nov - 14 Nov

A beach with palm trees, umbrellas, and people.

12. Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Waikiki

Ashlyn G.

AED 948 total

includes taxes & fees

11 Nov - 12 Nov

A balcony with a view of a beach and ocean, furnished with a table, chairs, and a cat tree.

13. Panoramic Oceanview Resort

Waikiki

"The room was spotless and pristine, just like a model home, and the ocean view from the balcony was absolutely stunning. Everything was exactly as we had hoped! We were traveling with my in-laws, so the peaceful location a little away from the busy town center was perfect for us. They were absolutely blown away by the beauty of the place, saying, “This is paradise! Did we somehow end up in heaven?” It was wonderful to see them so happy! I would definitely come back for our next trip :)"

Kaori

AED 2,186 total

includes taxes & fees

13 Nov - 14 Nov

A modern hotel room with a grey sofa, a wooden coffee table, and a balcony with a view of high-rise buildings.

14. Aston at the Waikiki Banyan

Waikiki

Josephine

AED 785 total

includes taxes & fees

4 Dec - 5 Dec

A modern apartment with a kitchen, dining area, and a balcony with a view of the ocean.

15. Midway at the Waikiki Banyan

Waikiki

Dave

AED 1,755 total

includes taxes & fees

17 Nov - 18 Nov

16. Corner Unit Studio@Waikiki Hotel Building 1 day min

Waikiki

Manuel

AED 929 total

includes taxes & fees

8 Nov - 9 Nov

A beach with palm trees and a row of colorful surfboards leaning against a fence.

17. Aloha Suite Near the Sea II, 3 Block Walk to Beach

Waikiki

kwinam

AED 1,037 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a sofa, coffee table, and a view of the city through large windows.

18. Island Colony (IC14)

Waikiki

Nevena

AED 1,313 total

includes taxes & fees

9 Nov - 10 Nov

A tiki statue in a garden with palm trees and tropical plants, under a covered walkway.

19. Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

Waikiki

April B.

AED 972 total

includes taxes & fees

11 Nov - 12 Nov

A balcony with a view of a cityscape, furnished with a table, chairs, and a decorative wall.

20. Luana Waikiki by Tropical Escapes Realty

Waikiki

Kate Elizabeth

AED 1,627 total

includes taxes & fees

10 Nov - 11 Nov

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Find vacation rentals that suit your style

Top Kailua Hotel Reviews

A serene waterfront property with a wooden deck, lounge chairs, and lush greenery.

Paradise Bay Resort

Kahaluʻu

10/10 Excellent

Glenn

A poolside area with lounge chairs and umbrellas, overlooking the ocean at sunset.

Halepuna Waikiki by Halekulani

Waikiki

10/10 Excellent

The location and ocean were nice. It was very quiet except for the sounds of the ocean and you didn't know if guests were next door or in the hall. The towels, yes the towels, were very absorbant and soaked up the water on your skin. (Important factor for me) Room size was smaller than expected but I didnt go there to stay in the hotel and the beds were comfortable. Spa services were amazing. Parking was simple. Very organized and efficient. Had one concern and it was handled swiftly. I...

Diane

A kitchen with a view of the ocean and cityscape, featuring a marble countertop, modern appliances, and a built-in oven.

Holiday Inn Express Waikiki by IHG

Waikiki

10/10 Excellent

Montana

A hotel room with a large bed, two bedside tables with lamps, a view of the ocean, and a patterned wall.

OUTRIGGER Waikiki Paradise Hotel

Waikiki

10/10 Excellent

Yvonne

A hotel with outdoor seating, a pool, and a prominent building with a triangular roof structure.

OUTRIGGER Reef Waikiki Beach Resort

Waikiki

10/10 Excellent

A gym with various exercise equipment, including treadmills, elliptical machines, and weight machines.

Ramada Plaza by Wyndham Waikiki

Waikiki

Lizet

Frequently Asked Questions

Are there vacation rentals in Kailua?

Yes, we offer vacation rentals near the most popular sights in Kailua, or you can select a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

What are some of the best vacation home rentals in Kailua?

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY: This Kailua vacation home rental is located on the beach and has a balcony, a private yard, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Kailua are BEST LICENSED LOCATION The VIEWHOUSE LANIKAI 1990NUC-1739 and Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa..

How many vacation rentals are there in Kailua?

With 139 Expedia vacation rentals, you're sure to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Kalama Beach Park and Kailua Bay Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favorite places to visit like Ala Moana Center and Waikiki Beach Walk in the larger area.

What’s a vacation rental in Kailua like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.

Kailua Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Kailua vacation rentals

1. Luxurious five-bedroom modern retreat

2. Bishop Suites Downtown Honolulu

3. Skyline Island Colony Hotel

4. Aston Waikiki Sunset

5. Partial Ocean View Condo with King or Queen Bed and Parking

6. Royal Kuhio

7. Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop

8. Regency on Beachwalk Waikiki by OUTRIGGER

9. Ilikai Marina Vacations

10. Charming cozy condo in marvelous Honolulu with WiFi

11. Modern, renovated studio in Waikiki

12. Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

13. Panoramic Oceanview Resort

14. Aston at the Waikiki Banyan

15. Midway at the Waikiki Banyan

16. Corner Unit Studio@Waikiki Hotel Building 1 day min

17. Aloha Suite Near the Sea II, 3 Block Walk to Beach

18. Island Colony (IC14)

19. Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

20. Luana Waikiki by Tropical Escapes Realty

Find vacation rentals that suit your style

Top Kailua Hotel Reviews

Paradise Bay Resort

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Kailua?

What are some of the best vacation home rentals in Kailua?

How many vacation rentals are there in Kailua?

What’s there to see and do in Kailua?

What’s a vacation rental in Kailua like?