Cheap Vacations in Kailua

Choose two or more items and save on your trip:

3-night Kailua vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Waikiki Beach Resort & Spa

Hilton Waikiki Beach Resort & Spa

4 out of 5
Price was $879, price is now $700 per person
$700
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

3 out of 5
Save 100% on your flight
Price was $1,659, price is now $818 per person
$818
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana Hotelcondo by Luana Vacation Rental

3.5 out of 5
Save 100% on your flight
Price was $1,759, price is now $925 per person
$925
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
Price was $1,429, price is now $965 per person
$965
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
Price was $1,562, price is now $1,171 per person
$1,171
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
The Royal Hawaiian, a Luxury Collection Resort, Waikiki

The Royal Hawaiian, a Luxury Collection Resort, Waikiki

5 out of 5
Price was $1,492, price is now $1,153 per person
$1,153
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Stay Hotel Waikiki

Stay Hotel Waikiki

3 out of 5
Price was $909, price is now $719 per person
$719
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Prince Waikiki

Prince Waikiki

4.5 out of 5
Price was $1,143, price is now $931 per person
$931
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Wayfinder Waikiki

Wayfinder Waikiki

4 out of 5
Price was $1,146, price is now $940 per person
$940
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Pagoda Hotel

Pagoda Hotel

2 out of 5
Price was $858, price is now $711 per person
$711
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
OUTRIGGER Waikiki Beachcomber Hotel

OUTRIGGER Waikiki Beachcomber Hotel

4 out of 5
Price was $1,007, price is now $837 per person
$837
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
OUTRIGGER Waikiki Beach Resort

OUTRIGGER Waikiki Beach Resort

4 out of 5
Price was $1,402, price is now $1,169 per person
$1,169
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)

4-night Kailua vacations

Price found within the past 48 hours. Click for updated prices.
Waikiki Resort Hotel

Waikiki Resort Hotel

3.5 out of 5
Save 100% on your flight
Price was $881, price is now $500 per person
$500
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana Hotelcondo by Luana Vacation Rental

3.5 out of 5
Price was $6,204, price is now $2,551 per person
$2,551
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

3 out of 5
Price was $2,066, price is now $929 per person
$929
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
Save 100% on your flight
Price was $1,271, price is now $849 per person
$849
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,675, price is now $1,175 per person
$1,175
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Royal Kuhio

Royal Kuhio

3.5 out of 5
Save 100% on your flight
Price was $1,019, price is now $716 per person
$716
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Stay Hotel Waikiki

Stay Hotel Waikiki

3 out of 5
Price was $813, price is now $576 per person
$576
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
Save 100% on your flight
Price was $1,308, price is now $954 per person
$954
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Waikiki Circle Hotel

Waikiki Circle Hotel

3 out of 5
Price was $894, price is now $667 per person
$667
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Pagoda Hotel

Pagoda Hotel

2 out of 5
Price was $718, price is now $539 per person
$539
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Best Western The Plaza Hotel Honolulu Airport - Free Breakfast

Best Western The Plaza Hotel Honolulu Airport - Free Breakfast

3 out of 5
Price was $836, price is now $644 per person
$644
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Airport Honolulu Hotel, Trademark Collection by Wyndham

Airport Honolulu Hotel, Trademark Collection by Wyndham

2.5 out of 5
Price was $786, price is now $613 per person
$613
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)

5-night Kailua vacations

Price found within the past 48 hours. Click for updated prices.
Waikiki Resort Hotel

Waikiki Resort Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,096, price is now $547 per person
$547
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana Hotelcondo by Luana Vacation Rental

3.5 out of 5
Price was $2,605, price is now $1,141 per person
$1,141
per person
Feb 5 - Feb 10
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

3 out of 5
Price was $2,647, price is now $1,255 per person
$1,255
per person
Feb 6 - Feb 11
found 17 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
Save 100% on your flight
Price was $1,367, price is now $819 per person
$819
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Stay Hotel Waikiki

Stay Hotel Waikiki

3 out of 5
Save 100% on your flight
Price was $963, price is now $642 per person
$642
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $2,271, price is now $1,520 per person
$1,520
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Honolulu (HNL)
Royal Kuhio

Royal Kuhio

3.5 out of 5
Save 100% on your flight
Price was $1,252, price is now $846 per person
$846
per person
Jan 24 - Jan 29
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Prince Waikiki

Prince Waikiki

4.5 out of 5
Save 100% on your flight
Price was $1,257, price is now $873 per person
$873
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Embassy Suites by Hilton Waikiki Beach Walk

Embassy Suites by Hilton Waikiki Beach Walk

4 out of 5
Save 100% on your flight
Price was $1,331, price is now $928 per person
$928
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Wayfinder Waikiki

Wayfinder Waikiki

4 out of 5
Save 100% on your flight
Price was $1,584, price is now $1,116 per person
$1,116
per person
Jan 15 - Jan 20
found 9 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Airport Honolulu Hotel, Trademark Collection by Wyndham

Airport Honolulu Hotel, Trademark Collection by Wyndham

2.5 out of 5
Price was $847, price is now $611 per person
$611
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Pagoda Hotel

Pagoda Hotel

2 out of 5
Price was $776, price is now $560 per person
$560
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)

6-7 night Kailua vacations

Price found within the past 48 hours. Click for updated prices.
Stay Hotel Waikiki

Stay Hotel Waikiki

3 out of 5
Save 100% on your flight
Price was $1,147, price is now $745 per person
$745
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

3 out of 5
Price was $3,415, price is now $1,413 per person
$1,413
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
Save 100% on your flight
Price was $2,010, price is now $1,162 per person
$1,162
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Royal Kuhio

Royal Kuhio

3.5 out of 5
Save 100% on your flight
Price was $1,394, price is now $897 per person
$897
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Wayfinder Waikiki

Wayfinder Waikiki

4 out of 5
Save 100% on your flight
Price was $1,545, price is now $1,045 per person
$1,045
per person
Jan 28 - Feb 4
just found
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
'Alohilani Resort Waikiki Beach

'Alohilani Resort Waikiki Beach

5 out of 5
Save 100% on your flight
Price was $1,363, price is now $926 per person
$926
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $2,328, price is now $1,588 per person
$1,588
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Waikiki Resort Hotel

Waikiki Resort Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $909 per person
$909
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
OUTRIGGER Waikiki Beach Resort

OUTRIGGER Waikiki Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,114, price is now $1,499 per person
$1,499
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Waikiki Place - the Place to be in Waikiki

Waikiki Place - the Place to be in Waikiki

3.5 out of 5
Save 100% on your flight
Price was $2,026, price is now $1,439 per person
$1,439
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Prince Waikiki

Prince Waikiki

4.5 out of 5
Save 100% on your flight
Price was $1,673, price is now $1,204 per person
$1,204
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)
Embassy Suites by Hilton Waikiki Beach Walk

Embassy Suites by Hilton Waikiki Beach Walk

4 out of 5
Save 100% on your flight
Price was $1,564, price is now $1,140 per person
$1,140
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Honolulu (HNL)

Flight deals to Kailua

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 21 - Wed, Jan 28
SEA
Seattle
HNL
Oahu
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 21 from Seattle to Oahu, returning Wed, Jan 28, priced at $239 found 2 days ago
Fri, Mar 13 - Wed, Mar 18
PAE
Seattle
HNL
Oahu
$243 Roundtrip, found 3 days ago
$243
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Mar 13 from Seattle to Oahu, returning Wed, Mar 18, priced at $243 found 3 days ago
Wed, Jan 7 - Fri, Jan 16
YVR
Vancouver
HNL
Oahu
$251 Roundtrip, found 6 days ago
$251
Roundtrip
found 6 days ago
Select WestJet flight, departing Wed, Jan 7 from Vancouver to Oahu, returning Fri, Jan 16, priced at $251 found 6 days ago

Top rated hotels for your Kailua vacation

Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
2255 Kalakaua Ave Honolulu HI
10.35 mi from city center
$541 nightly
The price is $642 total per night
$642 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
With a stay at Sheraton Waikiki Beach Resort in Honolulu (Waikiki), you'll be steps from Royal Hawaiian Center and 4 minutes by foot from Waikiki Beach Walk.
Pool
Hot Tub
Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

4.5 out of 5
2005 Kalia Rd Honolulu HI
Free Cancellation
Reserve now, pay when you stay
10.4 mi from city center
$327 nightly
The price is $388 total per night
$388 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
With a stay at Hilton Hawaiian Village Waikiki Beach Resort in Honolulu (Waikiki), you'll be a 2-minute drive from Ala Moana Center and 5 minutes from Honolulu Zoo.
Pool
Spa
Hyatt Regency Waikiki Beach Resort & Spa

Hyatt Regency Waikiki Beach Resort & Spa

4 out of 5
2424 Kalakaua Ave Honolulu HI
10.31 mi from city center
$264 nightly
The price is $313 total per night
$313 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located in Honolulu (Waikiki), Hyatt Regency Waikiki Beach Resort & Spa is a 3-minute walk from Kuhio Beach and 6 minutes by foot from International Market Place.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Kailua
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.