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Kailua Holiday Rentals

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Kailua holiday rentals

BBQ/picnic Area
Skyline Island Colony Hotel

Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2133)
"Have stayed here a couple of times and always had a great experience "
Canada
Aida
The price is S$277
includes taxes & fees
23 Dec - 24 Dec
Skyline Island Colony Hotel
BBQ/picnic Area
Aston Waikiki Sunset

Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3074)
"Slightly dated and older carpets/hallways but rooms are clean and it has everything you need. Great place to stay for a reasonable price in Waikiki. "
Canada
Josh
The price is S$287
includes taxes & fees
13 Jan - 14 Jan, 2026
Aston Waikiki Sunset
Living area
Aston at the Waikiki Banyan

Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.2 out of 10, Good, (2676)
"Amazing check on smooth friendly amazing room and view will only stay here when I visit now! "
United States
John
The price is S$262
includes taxes & fees
11 Jan - 12 Jan, 2026
Aston at the Waikiki Banyan
Beach/ocean view
Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre
4.0 star property
Downtown Honolulu
7.6 out of 10, Good, (71)
"great"
China
Jiachen
The price is S$224
includes taxes & fees
13 Jan - 14 Jan, 2026
Bishop Suites At The Executive Centre
View from room
Aston Waikiki Beach Tower

Aston Waikiki Beach Tower

Aston Waikiki Beach Tower
4.0 star property
Waikiki
9.2 out of 10, Wonderful, (1809)
"Excellent service, great location, and beautiful views from our 2/2 condo balcony beachside. "
United States
Mary
The price is S$1,056
includes taxes & fees
4 Jan - 5 Jan, 2026
Aston Waikiki Beach Tower
On the beach, sun-loungers, beach umbrellas
Castle Waikīkī Shore

Castle Waikīkī Shore

Castle Waikīkī Shore
3.0 star property
Waikiki
8.4 out of 10, Very good, (1234)
"The location was perfect 5/5 "
United States
Jackelin
Castle Waikīkī Shore
Beach nearby
Royal Kuhio

Royal Kuhio

Royal Kuhio
3.5 star property
Waikiki
8.6 out of 10, Excellent, (527)
"Very clean, great location, we enjoyed our stay."
United States
Kris Parkinson
The price is S$363
includes taxes & fees
18 Dec - 19 Dec
Royal Kuhio
Beach/ocean view
Espacio The Jewel Of Waikiki

Espacio The Jewel Of Waikiki

Espacio The Jewel Of Waikiki
5.0 star property
Waikiki
9.8 out of 10, Exceptional, (21)
"The hotel was great, the staff were amazing, and the view from the balcony was beautiful."
United States
Andrew
The price is S$4,499
includes taxes & fees
13 Jan - 14 Jan, 2026
Espacio The Jewel Of Waikiki
Premium bedding, individually decorated, individually furnished, desk
Panoramic Oceanview Resort

Panoramic Oceanview Resort

Panoramic Oceanview Resort
4.0 star property
Waikiki
The price is S$1,078
includes taxes & fees
11 Jan - 12 Jan, 2026
Panoramic Oceanview Resort
Terrace/patio
Regency on Beachwalk Waikiki by OUTRIGGER

Regency on Beachwalk Waikiki by OUTRIGGER

Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
Waikiki
8.2 out of 10, Very good, (431)
"Excellent location. Close to everything "
United States
Inna G
The price is S$994
includes taxes & fees
18 Dec - 19 Dec
Regency on Beachwalk Waikiki by OUTRIGGER
View from room
Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER
3.0 star property
Waikiki
8.4 out of 10, Very good, (542)
"Great location and amazing views. Clean and quiet. Bonus was the Steak Shack on ground level!"
Australia
Matt
The price is S$1,007
includes taxes & fees
21 Dec - 22 Dec
Waikiki Shore by OUTRIGGER
Terrace/patio
Luana Waikiki by Tropical Escapes Realty

Luana Waikiki by Tropical Escapes Realty

Luana Waikiki by Tropical Escapes Realty
2.5 star property
Waikiki
8.0 out of 10, Very good, (54)
"Close to the stores and beach. Quiet "
United States
Virginia
The price is S$449
includes taxes & fees
21 Dec - 22 Dec
Luana Waikiki by Tropical Escapes Realty
Beach nearby, white sand, beach towels, snorkelling
Premium Remodeled Condo in Waikiki with 2 Beds and Parking

Premium Remodeled Condo in Waikiki with 2 Beds and Parking

Premium Remodeled Condo in Waikiki with 2 Beds and Parking
4.0 star property
Waikiki
10.0 out of 10, Exceptional, (12)
"Breathtaking view, clean and with all we needed, this apartment exceeded our expectations! "
United States
Daniela
The price is S$665
includes taxes & fees
13 Jan - 14 Jan, 2026
Premium Remodeled Condo in Waikiki with 2 Beds and Parking
On the beach, white sand
High Floor Ocean View Condo (King Bed and Parking)

High Floor Ocean View Condo (King Bed and Parking)

High Floor Ocean View Condo (King Bed and Parking)
3.5 star property
Waikiki
9.4 out of 10, Exceptional, (43)
"Prime Location and sunset can be seen from room itself. "
United States
Shubham
The price is S$574
includes taxes & fees
13 Jan - 14 Jan, 2026
High Floor Ocean View Condo (King Bed and Parking)
Interior detail
Mountain View Condo with King or Queen Bed and Parking

Mountain View Condo with King or Queen Bed and Parking

Mountain View Condo with King or Queen Bed and Parking
3.5 star property
Waikiki
8.4 out of 10, Very good, (9)
"The room was clean, spacious, and very comfortable. I would like to stay here again. I would also recommend it to Japanese people"
Japan
KATSUHIDE
The price is S$560
includes taxes & fees
13 Jan - 14 Jan, 2026
Mountain View Condo with King or Queen Bed and Parking
Iron/ironing board, free WiFi
Island Colony hotel

Island Colony hotel

Island Colony hotel
2.5 star property
Waikiki
The price is S$395
includes taxes & fees
18 Dec - 19 Dec
Island Colony hotel
Beach nearby, white sand, beach towels
Ocean View 1BR at Ilikai Marina

Ocean View 1BR at Ilikai Marina

Ocean View 1BR at Ilikai Marina
3.0 star property
Waikiki
9.4 out of 10, Exceptional, (8)
"Great location for family with kids."
United States
Christopher Yong Seung
The price is S$592
includes taxes & fees
18 Dec - 19 Dec
Ocean View 1BR at Ilikai Marina
Building design
Ilikai Marina Vacations

Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.4 out of 10, Very good, (33)
"Clean and good use of space. "
United States
Cristina Katia Garcia
The price is S$482
includes taxes & fees
13 Jan - 14 Jan, 2026
Ilikai Marina Vacations
Individually decorated, individually furnished, blackout curtains
Marine Surf by Tropical Escapes Realty

Marine Surf by Tropical Escapes Realty

Marine Surf by Tropical Escapes Realty
3.0 star property
Waikiki
8.8 out of 10, Excellent, (58)
"Great experience "
United States
Dawn Marie
The price is S$506
includes taxes & fees
6 Jan - 7 Jan, 2026
Marine Surf by Tropical Escapes Realty
Beach nearby, white sand, beach towels
Cozy Studios at Aloha Surf Close to Waikiki Beach

Cozy Studios at Aloha Surf Close to Waikiki Beach

Cozy Studios at Aloha Surf Close to Waikiki Beach
3.0 star property
Waikiki
9.6 out of 10, Exceptional, (7)
"The stay was amazing very lovely cozy place we enjoyed our stay , the only downfall can be the parking but we got lucky all days to be able to find free parking at walking distance."
United States
Margarita
The price is S$465
includes taxes & fees
13 Jan - 14 Jan, 2026
Cozy Studios at Aloha Surf Close to Waikiki Beach
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

Ramada Plaza by Wyndham Waikiki

Ramada Plaza by Wyndham Waikiki

10/10 Excellent
"The hotel staff friendly and answer any question I had. The hotel in Waikiki which is walking distance to the beaches. The room was clean and very nice. "
Antonio 11-night trip
Posted 23 hours ago
Ramada Plaza by Wyndham Waikiki

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Frequently asked questions

Are there holiday rentals in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

How many holiday rentals are there in Kailua?

With 155 Expedia holiday rentals, you're guaranteed to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Kailua Bay Beach and Kailua Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Ala Moana Center and Waikiki Beach in the wider area.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.