Downtown Kailua Vacation Packages for 2026

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Top Hotel Deals

Hyatt Regency Waikiki Beach Resort & Spa

Hyatt Regency Waikiki Beach Resort & Spa

4 out of 5
2424 Kalakaua Ave Honolulu HI
15.72 km from Downtown Kailua
Book a stay at this spa resort in Honolulu. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in ...
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
2255 Kalakaua Ave Honolulu HI
15.81 km from Downtown Kailua
Book a stay at this luxury hotel in Honolulu. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

4.5 out of 5
2005 Kalia Rd Honolulu HI
15.93 km from Downtown Kailua
Book a stay at this luxury resort in Honolulu. Enjoy 5 outdoor pools, a full-service spa, and 9 restaurants. Our guests praise the pool and the helpful staff ...
'Alohilani Resort Waikiki Beach

'Alohilani Resort Waikiki Beach

5 out of 5
2490 Kalakaua Avenue Honolulu HI
15.75 km from Downtown Kailua
Book a stay at this luxury resort in Honolulu. Enjoy free WiFi, 5 restaurants, and a rooftop terrace. Our guests praise the pool and the helpful staff in our ...
Waikiki Beach Marriott Resort & Spa

Waikiki Beach Marriott Resort & Spa

4 out of 5
2552 Kalakaua Ave Honolulu HI
15.85 km from Downtown Kailua
Book a stay at this spa resort in Honolulu. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Waikiki Resort Hotel

Waikiki Resort Hotel

3.5 out of 5
2460 Koa Avenue Honolulu HI
15.69 km from Downtown Kailua
Book a stay at this family-friendly hotel in Honolulu. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Holiday Inn Express Waikiki by IHG

Holiday Inn Express Waikiki by IHG

3 out of 5
2058 Kuhio Avenue Honolulu HI
15.37 km from Downtown Kailua
Book a stay at this family-friendly hotel in Honolulu. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Best Western The Plaza Hotel Honolulu Airport - Free Breakfast

Best Western The Plaza Hotel Honolulu Airport - Free Breakfast

3 out of 5
3253 N Nimitz Hwy Honolulu HI
19.09 km from Downtown Kailua
Book a stay at this business-friendly hotel in Honolulu. Enjoy free breakfast, a free airport shuttle, and a fitness center. Our guests praise the breakfast ...
The Twin Fin Hotel

The Twin Fin Hotel

4 out of 5
2570 Kalakaua Ave Honolulu HI
15.9 km from Downtown Kailua
Book a stay at this beach hotel in Honolulu. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the pool in our ...
Sheraton Princess Kaiulani Waikiki Beach

Sheraton Princess Kaiulani Waikiki Beach

4 out of 5
120 Kaiulani Ave Honolulu HI
15.66 km from Downtown Kailua
Stay at this hotel in Honolulu. Enjoy breakfast (surcharge), a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff ...
Ramada Plaza by Wyndham Waikiki

Ramada Plaza by Wyndham Waikiki

3 out of 5
1830 Ala Moana Blvd Honolulu HI
15.66 km from Downtown Kailua
Stay at this hotel in Honolulu. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
Wayfinder Waikiki

Wayfinder Waikiki

4 out of 5
2375 Ala Wai Blvd Honolulu HI
15.35 km from Downtown Kailua
Stay at this hotel in Honolulu. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the pool and the restaurant in our reviews. ...
OUTRIGGER Reef Waikiki Beach Resort

OUTRIGGER Reef Waikiki Beach Resort

4.5 out of 5
2169 Kalia Rd Honolulu HI
15.95 km from Downtown Kailua
Book a stay at this luxury resort in Honolulu. Enjoy free WiFi, 2 restaurants, and 3 hot tubs. Our guests praise the breakfast and the pool in our reviews. Popular ...
Prince Waikiki

Prince Waikiki

4.5 out of 5
100 Holomoana St Honolulu HI
15.79 km from Downtown Kailua
Book a stay at this luxury resort in Honolulu. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the restaurant in our reviews. ...
Halepuna Waikiki by Halekulani

Halepuna Waikiki by Halekulani

4.5 out of 5
2233 Helumoa Road Honolulu HI
15.87 km from Downtown Kailua
Book a stay at this luxury hotel in Honolulu. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Mon, Nov 30 - Fri, Dec 11
SFO
San Francisco Intl.
HNL
Daniel K. Inouye Intl.
$325 Roundtrip, found 5 days ago
$325
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Mon, Nov 30 from San Francisco Intl. to Daniel K. Inouye Intl., returning Fri, Dec 11, priced at $325 found 5 days ago
United
Mon, Nov 30 - Fri, Dec 11
SFO
San Francisco Intl.
HNL
Daniel K. Inouye Intl.
$325 Roundtrip, found 5 days ago
$325
Roundtrip
found 5 days ago
Select United flight, departing Mon, Nov 30 from San Francisco Intl. to Daniel K. Inouye Intl., returning Fri, Dec 11, priced at $325 found 5 days ago
American Airlines
Mon, Nov 30 - Fri, Dec 11
SFO
San Francisco Intl.
HNL
Daniel K. Inouye Intl.
$344 Roundtrip, found 5 days ago
$344
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Nov 30 from San Francisco Intl. to Daniel K. Inouye Intl., returning Fri, Dec 11, priced at $344 found 5 days ago
Delta
Tue, Jan 5 - Tue, Jan 12
SFO
San Francisco Intl.
HNL
Daniel K. Inouye Intl.
$344 Roundtrip, found 2 hours ago
$344
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jan 5 from San Francisco Intl. to Daniel K. Inouye Intl., returning Tue, Jan 12, priced at $344 found 2 hours ago
Southwest Airlines
Mon, Nov 30 - Fri, Dec 4
SAN
San Diego Intl.
HNL
Daniel K. Inouye Intl.
$356 Roundtrip, found 4 days ago
$356
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Nov 30 from San Diego Intl. to Daniel K. Inouye Intl., returning Fri, Dec 4, priced at $356 found 4 days ago