Are you in the process of planning a trip to Hawaii? If you are, you are no doubt trying to find the best places to stay in Hawaii. In addition to hotels, you may also be interested in booking a stay at a Hawaiian vacation rental. Although Hawaiian vacation rentals may differ from typical hotels and resorts, they offer more privacy and beauty, especially when compared with traditional lodging options. Vacation rentals in Hawaii are increasing in popularity and learning how to find the best places to stay can make a good vacation a great one.

*Disclaimer: This post may contain affiliate links. If you make a purchase through one of these links, I will earn a small commission. This occurs at no added cost to you.*

Why Book a Hawaiian Vacation Rental Property?

As you likely already know, you will have several different options when making reservations for a vacation rental in Hawaii. The phrase “vacation rentals” is often used to describe several establishments, including vacation homes, vacation apartment rentals, vacation villas, vacation cottages, and vacation condos. Whether you are going to Hawaii as a solo, a couple, a family with children or an intergenerational family, you will be sure to find something that suits your needs and budget.

Sheraton Waikiki - hotel
Sheraton Waikiki is one of the best places to stay on the beach

Renting a home or condo allows you to customize your stay and have more space than you’d get at a hotel. Plus, as a bonus, it’s often cheaper than staying at resorts. But finding the right rental can be tricky: there are so many options out there that sorting through them all to find the best place to stay can take up valuable time and resources.

If you want to find the perfect vacation rental for your next trip, here are eight tips that will help narrow down your search and save you time:

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8 Tips to Finding the Best Places to Stay on Hawaii

1. Know What You Want in a Hawaiian Vacation Rental

Knowing what you want is one of the best ways to find the perfect vacation rental in Hawaii. Knowing what you want is the best way to have a great vacation regardless of the location!.

When examining your vacation wants, it is crucial to explore the purpose of your holiday. For example, if you are taking a Hawaii trip with your family, you may wish for affordability and convenience. On the other hand, if your Hawaii trip has romantic purposes, you may look more for beauty, elegance, and privacy. You are better suited for a more remote island such as Maui rather than the most famous island of Oahu, with its capital Honolulu. Determining the purpose of your vacation is key to selecting the best places to stay in Hawaii.

Hawaiian vacation rental near lagoon in waikiki
Selecting a vacation rental in Waikiki near the lagoon is great for families with young children

2. Determine your location.

The first step in finding the perfect vacation rental is determining your location. Depending on your preferences, this could be a beachfront house or a condo next to the pool. If you’re looking for peace and quiet, choose a place away from restaurants and busy areas. Additionally, it’s essential to consider how much driving or walking you’re willing to do before deciding on your desired location.

When considering Hawaii, it is also important to choose which island to visit. Are you a surfer? Perhaps finding a place to stay in Maui is where you want to be. If snorkeling or diving is your thing, do a little research and decide which island has the better reefs and beaches for your desired marine life. Finding a place to stay within a short distance will be fantastic if you plan on diving every day. Finding a Hawaiian vacation rental near shallow, calm beaches may be more desirable for children than rocky shorelines or bustling city streets.

Hawaiian vacation rental on the beach (1)
A Hawaiian vacation rental on the beach can offer easy access if you are a watersports enthusiast

3. Choose Your vacation Type

When it comes to your Hawaiian vacation rental, you have three main choices: house, condo, or apartment. The beach areas are more popular with vacationers than the mountains, but you can find rentals in both. If you plan on staying for a few months or longer, then a long-term lease might be best for you; if not, consider a short-term lease. Detailed research will help you determine what your needs are. If you are coming as a large family or group, you will probably have more bang for your buck in a separate house of apartment rather than hotel rooms.

What is nice about researching and examining your accommodation options is that it is easy to do with the internet. Many online travel websites, especially those that deal specifically with Hawaii trips, allow you to find many vacation rentals quickly. You can examine pictures and other information to see if you should stay at a Hawaii vacation home, Hawaii vacation condo, villa, cottage, or apartment rental.

Waikiki at night
If nightlife is a consideration, perhaps Waikiki is the best place to stay on Hawaii

4. Check for Ratings, Reviews, and Amenities

Once you have found a rental that looks interesting, check for ratings and reviews. When looking for a place to stay, it’s always best to check out what previous visitors have had to say about the property. If there are many positive reviews from happy customers, that’s a good sign.

Look for amenities. If you’re renting a house or condo, find out what extras are available on-site (e.g., pool, gym). This way, you can plan your Hawaiian vacation accordingly and ensure your needs will be met while staying at the property in question.

Find out if there are additional fees involved with renting the accommodation itself or when booking tours through the owner of this home-away-from-home; sometimes owners charge cleaning fees or other expenses not included in the base price quoted by websites such as VRBO/HomeAway and Airbnb (which I would highly recommend using).

5. Consider cost and fees vs. value-added perks.

Consider cost and fees vs. value-added perks. Are you looking for a tropical vacation, or is it more about the experience? Do you want to stay close to nature, or are you more concerned with access to local attractions? All these factors are points to consider when selecting your vacation destination and rental.

If you are a more mature traveler, this article on Top Considerations for Hawaiian Visitors Over 50 highlights some interesting points about accessibility, availability, and mobility. These may be important for you when booking a place to stay in Hawaii. 

One of the best places to stay on Hawaii - hostels
Hawaii can be expensive. Perhaps a hostel is more to your taste

6. Book Directly with the Property Manager.

Whenever possible, book directly with the property manager. When you book through a third party, like Airbnb or VRBO, they charge you a service fee for every transaction. This can add up to hundreds of dollars for your Hawaii vacation rental! If you’re staying at an Airbnb, this is called “host service fees,” which can be as much as 20% of your total stay. With the direct booking, there are no hidden costs or fees to pay. You also get better customer service because the property manager is always available to help if anything goes wrong during your stay or if anything comes up while planning your trip that needs attention immediately.

Booking directly can also give you special deals and discounts. Some properties offer guests special rates just for booking directly with them rather than via another site as an incentive for booking directly. In contrast to VRBO, which takes its commission out of every transaction when someone stays in their listings, some properties offer special rates just for direct bookings.

VBRO vacation rental in Hawaii
Booking directly can get you better discounts and avoid service fees

7. Examine Nearby Activities

Unfortunately, many individuals believe that the most critical part of choosing a Hawaii vacation rental is determining the rental that is the perfect size or price for them. While these are all important factors that should be considered, you will also want to examine nearby Hawaii attractions and activities. For example, if you are interested in spending your Hawaii trip surfing, boating, or swimming, a beachfront or beach view rental may be your best option.

8. Make Your Reservations Early

As soon as you find a place to stay in Hawaii that you would like to book, it is important that you do so right away. As previously stated, Hawaii vacation rentals are a popular choice among tourists. If you act slowly, you may find that your first choice Hawaii vacation rental is already booked for your intended travel dates.

The right vacation rental can make a big difference in your trip to paradise.

A vacation rental can make all the difference in your trip to paradise. Whether you’re looking for a luxury villa or two-bedroom bungalow with all the amenities of home or need a place to stay while you explore Oahu’s many sights and sounds, there are many places to stay in Hawaii at your fingertips.

Westin Maui resort Kaanapali- best place to stay in Hawaii
Hawaiian vacation resorts can provide all the comforts of home as well as a slice of paradise

Being able to choose from a wide range of accommodations can be extremely helpful when planning your trip. For example, if your family has grown since last year and now includes an additional child or two along with Grandma and Grandpa, staying in a spacious four-bedroom house might be more comfortable than sharing one room between five people. Or would you rather sleep alone in an air-conditioned condo instead of sharing an air mattress on an uncomfortable futon couch every night? If so, choosing the right Hawaiian vacation rental will help ensure that everyone gets exactly what they want out of their Honolulu getaway!

It’s also important to remember that booking directly through property managers may save some money on hotel reservation fees. Hotels often charge additional fees for reserving rooms through third-party websites like Airbnb (even if those bookings are made through their website).

Luxury vacation rentals in Hawaii
Who wouldn’t want a Hawaiian vacation rental that has a view like this?

Conclusion – Finding the Best Places to Stay on Hawaii

Whether you’re looking for a condo or villa, luxury estate, or budget vacation rental, it’s essential to do your research before booking. The right Hawaiian vacation rental can make all the difference in your trip to paradise and choosing from among the many options available can be daunting. To make things easier on yourself, follow these eight tips for finding the best places to stay in Hawaii.

These tips mentioned above are just a few that can help you find, choose, and book the Hawaii vacation rental of your dreams. While you may not necessarily think about it at the time, your overnight accommodations can have a significant impact on the success of your next Hawaii trip. This is of particular importance if you are visiting Hawaii for the first time. A food experience will make you want to return!

As always, be sure to check your travel insurance requirements before you leave home. You do not want to be faced with a medical emergency while on your dream vacation on Hawaii.

The Perfect Travel Insurance

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Best Places to Stay on Hawaii

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5 Comments

  1. The second picture down is labeled “Sheraton Waikiki is one of the best places to stay on the beach.”
    Are you sure that’s the Sheraton Waikiki? This shows a low rise building —Sheraton on Waikiki Beach has numerous floors!
    Please correct otherwise, it’s misleading

  2. These days you have such a variety of options that you have to invest some effort and time to get the best deal. Sometimes a third party booking provider can be the best option, other times as you mention, a direct booking works best in your favour. It’s unfortunately a time consuming individual case by case.

    Carolin | Solo Travel Story

  3. Laura these are such good tips. Booking directly cannot be understated as my wife and I note the hundreds of dollars added on through AirBnb. The cleaning fees skyrocketed over the prior few years. I wonder why? LOL, of course. People saw opportunities to add 100 or 200 bucks based on collective fear to jack up prices. No thanks. Go direct or at least find a reputable person who charges minimum fees. Excellent advice here.

    Ryan

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