Hotel suggestions Oahu and Maui

For Oahu, we stayed at the Outrigger Reef Waikiki for a week. We got a great deal through Costco. It was a splurge trip for us - not cheap, but we got a huge room with a nice patio overlooking the beach. We spent 8 nights in a Club Oceanfront Room. The total cost was $4500 - so close to your budget. The Club level included a daily breakfast buffet and then an evening appetizer and drink spread that was so large that we just ate that for dinner 6 of our 8 nights.

The cost was further offset by a $300 Costco shop card that is like a credit at Costco and airport transfers.

I will add that we took a day tour of a gorgeous house there - Shangri La - and it’s worth trying to get into.
https://www.shangrilahawaii.org/about/. Great history, culture and architecture there!

For Maui, we’ve stayed at a lot of properties - mostly in Kihei and Wailea. But after a few visits, we started staying up north - in the Napili Kapalua area. It’s more remote from things - but we just mostly sit around on Maui. We LOVE the Napili Kai hotel. It’s a low-slung, old style beach/plantation hotel. It’s low-key and on an awesome beach. https://www.napilikai.com/

I suggest trying booking.com. It is a good site for research. You can book directly on the site or go to the website of the lodging and book there.

I went to Hawaii several years back and it is really beautiful and interesting.

Patricia,
Hubby and I went to Oahu in January this year. We stayed at the Queen Kapiolani Hotel for five nights (Mon to Sat.) for a room with two queen beds for under $1400.00 for the five nights. Booked through Booking.com. Our initial price there was about $2200.00, but I checked periodically after the first booking and saw a price drop, so I reserved at the new price and cancelled the first reservation. (I always book cancellable rate!) This included a discount I got from Booking.com as a frequent customer. The hotel was a short block to Waikiki Beach. Room was smallish with no coffeemaker, but the beds were comfortable and room was clean and well-tended. We walked about 2 long blocks away from the beach to catch buses to take us to various sights, using the HOLO card recommended by someone on this forum (senior rates available, unlimited use per day). We also used Lyft for evening excursions to restaurants. We did not have a view. I found in my search that a beach view really added to the cost of a room, and since we were out and about every day we didn't regret the lack of view due to the large amount of money we saved.
The floor that the pool was on had a bar/restaurant that had some happy hour specials, and we had meal there on our arrival night that was very good. We had a cocktail there almost every night (nice sunset views over the beach from this pool/bar/restaurant area).

Being 80 and 81, we didn't swim in the ocean, or do any strenuous activities, but enjoyed walking along the beach. Sights I would say to NOT miss are the Bishop Museum and the Arizona Memorial. We took the bus to and from each of these places. We also visited the Punchbowl National Veteran's Cemetery (best to use Uber or Lyft to get there) and the Friday noon musical concert at Queen Kapiolani Palace, a free treat and one of our fondest memories...chairs are provided. We walked about 1/4 to 1/2 mile from our hotel to another hotel to pick up a rental car for a day to drive to the North Shore, and stopped at many beaches to relish the scenery and views along the way.

We have been to Kauai twice and the big island once, but never Mauai, so can't offer any advice there. I will add that I love Hawaii (the big island) and would return in a heartbeat if the opportunity presented itself!

One last thing, we went to Duke's Waikiki on Thursday night for their all-you-can-eat prime rib dinner. Delicious food! Also, we celebrated a birthday at the "House Without a Key " restaurant another night. Not cheap, but delicious food. Also, the Barefoot Beach Cafe South of our hotel, right on the beach, was good, simple food with fun musical entertainment (outside eating) and a nice sunset stroll along the beach to get there from the hotel.

Have a wonderful time!

How many nights do you plan to be in Hawaii?

Are you trying to do both Oahu and Maui, or planning on just one island?

We're thinking 10 nights split in some way between Oahu and Maui.

Thanks for all of the replies so far!

Judy, how was your weather in January?

We liked the Ka'anapali Beach Hotel so much, we've stayed there four times. It's the best part of the best beach on Maui. Its been purchased and is now part of the Outrigger chain, and the name changed a bit: Kaanapali Beach Resort There are some places with similar names so google with care.

The downside being the fire that destroyed the town of Lahaina which is just down the road and where much of the shopping and restaurants were. We will still go back there however.

Patricia,
The weather was lovely. No mugginess as in the summer. One late afternoon there was some rain. (We enjoyed seeing it from the comfort of our table having cocktails at the hotel bar/restaurant called "The Deck".) It never rained during the day when we were out and about. Nov-Mar is the rainy season, but I wouldn't be deterred by rain since I am not aiming for a suntan, and am long past the age of wearing a bathing suit in public!

We're thinking 10 nights split in some way between Oahu and Maui

For me Oahu 3 nights and Maui 7 nights would be my top recommendation; 4/6 would be 2nd. choice. I would not do a 5/5 split.

We have always done condo rental so no help on hotels.

If you are a Costco member you may want to look at some of their package deals ( room and car)

If in Honolulu you want to splurge stay at the Royal Hawaiian. Beautiful pools and ocean front located in the center of Waikiki. But be aware that the rooms in the historic portion of the hotel may not have a/c. Rooms in the newer Mailani tower do have a/c and all have rooms in the tower have ocean views. Close by is the Moana Surfrider, another historic hotel, ocean front with lovely pools. At the quieter end of Waikiki is the Prince Waikiki. It has a lovely pool but is not on the beach. It has ocean front rooms and it overlooks the "Gilligan's Island" boat harbor. The Queen Kapiolani is at the other end of Waikiki from the Prince Waikiki. The Queen Kapiolani's rooms only have partial ocean views. It is located across the street from the Honolulu Zoo and near the aquarium. It's close to alot of places to eat and a protected beach suitable for non-open water swimming.

A couple of things. We were last in Waikiki last January, and Maui the previous January. Both times the water was a bit too cold for us. But if you go to Maui, in season (January-May), whale-watching is a good boat excursion.

The suggestions for Royal Hawaiian and Moana Surfrider are excellent. You may want to look at the Hilton Hawaiian. It is a HUGE resort ( you can get lost) but has at least 3 outdoor pools and an adult only pool. Prices are on the top end of your budget, especially if you go in the winter months.

If I were to stay in Waikiki, I would stay at the Kaimana Beach Hotel. It has no pool, but is small, at the quiet end of Kalakaua Ave ( right across from Kapiolani Park) and in front of a small life guarded beach, where monk seals occasionally sun themselves (when they do that, the ocean mammal protection group immediately cordons off the beach, but you can see the seal from your balcony)

If you like history and culture, take a Chinatown walking tour with the Hawaii Heritage Center. They will give a true insider look. Chinatown is one of my favorite places when I go back home. It’s a bit grungy, a bit sketchy, but fascinating and ever changing.

Maybe consider a native-owned or at least locally owned hotel/lodging? Especially in Maui where people are still struggling.

On Maui, check out Napili Kai Beach Resort — old style Hawaii, right on Napili Bay, excellent restaurant, low-rise buildings, great facility, various social activities.

Thanks to all for the great suggestions!

We ended up booking the Park Shore Waikiki on Oahu based on the recommendation of our son and his husband who stayed there last year. On Maui we chose the OUTRIGGER Kaanapali Beach Resort that Stan recommended (thanks, Stan!).

Patricia, one of the nice things about that place on Maui, is that you can walk just down the beach to the Whalers Village shopping center where there are restaurants (and shops of course), and when we were there, several excursions (whale watching, outrigger canoe ride, dinner cruise, snorkel, etc.) would launch from there. I don-t know how it is post-fire. I will say the parking is a bit snug at the hotel, so don't give up your space if you get a good one.

That hotel used to be locally owned, and prided itself on being the "most Hawaiian hotel" on the island. They had classes on culture, and local entertainment. It was sold to Outrigger, so I'd be interested in hearing about changes.