We have now been to Hawaii three times. The first two times we stayed on Maui and Kaua’i and the last time we stayed on Oahu and Kaua’i. All three of the islands are beautiful and part of the problem is deciding which islands to stay on and for how long. Each island is different. We love Maui and Kaua’i because they are more laid back and very lush and green. Oahu is much more populated and busy but also has wonderful places to visit and see. It would be great if you could visit all of the islands and stay for a week on each but that might be too long to be gone from home. We did choose to visit two islands each time and split our time between the two. I am going to list the places that we chose to stay on each island and give you some tips for finding your perfect vacation home away from home.
The first time we visited Hawaii, it was just my husband and I and we chose to stay in resorts. We did this partly because I didn’t know anything about the islands at all so I wasn’t sure what part of the islands to stay on or what a condo or house might be like. So I picked a moderately priced resort on each island – Maui and Kaua’i. You can pick much more expensive resorts and there are some very inexpensive places to stay as well. On Maui we stayed at the Hyatt Regency Resort & Spa in Lahaina. It was lovely. The grounds are spectacular with amazing flowers and waterfalls and trees. It also has a beach area which was one of the things that I researched before deciding on a place. I wanted at least some beach access. This resort also has a pond area with swans and a separate area with penguins. Every part of the facility is beautiful. They also have a spectacular luau on their grounds which is very convenient.
resort view of pool 
resort view of grounds 
resort grounds 
luau at the resort
In Kaua’i we stayed at the Kaua’i Marriott Resort. It is near the airport in Lihue and centrally located on the island. This resort is a little bit older but the grounds are lovely. They have a fantastic very large pool area with fountains and waterfalls and a bridge crossing onto an island in the middle. There is also a very nice beach area on Kalipaki Bay with chairs and volleyball nets and cabanas. Many restaurants and shops are within walking distance including the famous Duke’s, which is one of our favorites. Also on this bay you can snorkel, kayak, learn to surf or even take a catamaran tour up the river.
beach area at resort 
pool area at the resort 
beach at the resort
Traveler Tip: Use hotel points if you have them. There are resorts owned by most of the major hotel names somewhere on the islands.
Traveler Tip: If you are flying in on a flight that lands late in the evening, you will be very tired and it helps to stay closer to the airport. The Kaua’i Marriott is very close to the airport. The Hyatt is on the other side of the island of Kaua’i from the airport. This doesn’t mean you shouldn’t stay at a particular resort – just keep the time and distance in mind.
On our second trip, because our daughter was traveling with us, we chose to try VRBO and find a condo or house with multiple rooms instead of the resorts. It helped that we had already been to both islands once and kind of knew what area we wanted to stay in. So on this trip I chose places that had beach access with a swimming area. The one on Kaua’i was between Lihue (where the airport is) and Wailua. We stayed in a condo at Lae Nani and we loved it. It was a cute two bedroom place on the second floor with a great view. There is no air conditioning in most homes or condos, but with the fans and windows open, there is a nice breeze and it is comfortable most of the time. This home had a great beach and swimming area and was walking distance to Lava Lava Beach Club which is a great restaurant on the beach.
Lae Nani 
From the water 
The beach area at the condo 
View of the sunrise
Our next stop was on Maui and we chose a condo called Kahana Sunset. It was a little bit past Lahaina (which was one of our favorite little towns). It had a unique design with 2 bedrooms on the second floor up a split staircase. Again no air conditioning but lots of fans. This one had great views of the ocean and the island across from us. There was a small beach and swimming area but perfect sand and every afternoon the turtles came to eat on the rocks. We saw them almost every day. This location was nice because it was close to Lahaina for shopping and eating but also close to many other beaches.
View at our condo 
Turtle at our beach
On our third trip (which was in November of 2019) my husband and I went back for his surfing bucket list item. He really wanted to surf at Waikiki Beach on O’ahu and Hanalei Beach in Kaua’i. So I researched and booked again with VRBO. This time we found a little one room place right over the marina at Waikiki on the Ilikai building – the Ilikai Marina Condos. This place was really cool and within walking distance to the Hilton at Waikiki (that is the colored building that you see on the intro to Hawaii 50.) It is also right next to Ala Moana beach and park and just blocks from one of the largest shopping malls in Hawaii. Again there are plenty of resorts in this area as well, we just like staying in something a little homier and seeing how places are designed and styled. This one was excellent. Great studio layout and perfect for a couple.
Ilikai condos on the right 
View from the condo
Our second stop on this trip was Kaua’i and we stayed in 2 different places on this island this time. Because my husband wanted to surf at Hanalei we chose to stay up near there for the first several days. This time I researched the views. We stayed in Princeville (which is a residential area with many homes and resorts including the Princeville Resort and a golf course) and we stayed on the edge of a cliff overlooking the ocean – Sealodge condos. This view was spectacular and we could hear the waves crashing from inside the condo. No air conditioning but a wonderful breeze blowing all of the time and we left all of the windows open. It had two bedrooms and a nice seating area with a bay window (the view from all of the rooms was amazing) and a tiny balcony with a table, which we used for breakfast when we cooked here.
Sea Lodge Building 
View from the patio 
View from the bay window
Traveler Tip: Restaurants in Hawaii are very expensive. If you can cook at your home, it will help with expenses.
The next place on this trip was back toward the airport and in fact we rented a place on the cliff overlooking the Marriott that we had stayed at before. This was awesome because the home owner had arranged with the Marriott for guests to use the facilities. Again our view from up on this cliff was fantastic. We were overlooking the Kalipaki bay. The place was actually an apartment on the lower level of a very large house but the apartment was perfect for us. Cute seating area and kitchen and great outdoor patio. The bedroom in this one was air-conditioned with a small unit, which helped since the bedroom was in the back of the house. Also, there is an elevator to get off the cliff and down to the resort area so many shops and restaurants are still in walking distance.
Balcony view 
Breakfast view 
Night view 
Our house from the water
We actually rented one more room on our last day on this island. Every time we booked we ended up with a flight that left last in the evening and flew over night. This is nice because you have the extra day but can be a problem because if you go to beaches on your extra day where do you clean up and rest before going to the airport since you probably have to check out around 10:00 in the morning. So on this trip I found a hotel very close to the airport called Kaua’i Palms. It is small and older but cute and quaint and clean, and gave us the perfect place to go and take a nap and shower before heading to the airport.
Obviously there are so many choices of places to stay on the Hawaiian Islands. I hope this gives you some ideas and some things to think about when choosing your place to stay. One last thing, some people go to Hawaii and spend most of their time sight-seeing and adventure-seeking and others go to just relax. So keep that in mind when booking rooms as well. If you will just be laying be the pool or beach, you may want a resort. If you will be off on adventures then you just need a fairly central comfortable place to come back to and relax before your next outing. You really can’t go wrong if you research a little and pick what fits your vacation style. I hope this helps a bit.
Ocean view 
Bay view 
Beach view Night view
Aloha, Mahalo and Happy traveling!