Where to Stay

Best Condo Complexes on Oahu

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Finding just the right place to stay on Oahu can be tricky, especially with recent legislation limiting zoning for vacation rentals in residential areas.

If you’re looking for alternate accommodations (not a hotel or a resort), I tend to recommend condos over apartments and houses anyways as it puts less of a burden on local housing demands, however on Oahu, the options are self limiting now

Basically, properties that don’t have a permit to operate as a vacation rental and are outside of certain zones have been shut down (it’s estimated as many as 10,000 properties were being rented without permits on sites like Airbnb!) so if a hotel or resort isn’t in the budget (or you’ll looking for more amenities), a condo is a good option.

The condo situation on Oahu is interesting. Compared to the other islands, there are definitely fewer condos and complexes that cater to visitors as many of them (especially in Waikiki/Honolulu) have full time residents.

I’ve made recommendations for specific condo units in this post (mostly budget options), but availability, seasonal pricing, or other factors may leave you still needing more options.

In this post, I’m recommending several condo complexes (also called condo-tels or condo resorts) by area on Oahu that I think are good places to stay. I’ve also got descriptions of each area so you can figure out what part of the island is most appealing to you.

I think the best place to find (and book) Oahu vacation rentals is Vrbo. They’ve been around forever and are probably the most reputable booking platform online (with owners and vacationers alike), which means that you’ll find more quality properties listed on Vrbo than anywhere else online. I used to book more often with Airbnb, but I’ve begun to find that they often don’t have what I’m looking for (especially when I want to book a condo/unit within a resort property). So all of the condo complexes I will be linking to are bookable within Vrbo.

Disclaimer: This is by no means an exhaustive list of every condo complex on Oahu. There are soooooo many, and there likely are some that aren’t on this list that are perfectly good places to stay at. I’ve compiled this list largely based on location, ratings and reviews, and an overall vibe of what I’m looking for in a place to stay.

Turtle Bay (North Shore)

Oahu’s famous north shore stretches all the way from Laie to Haleiwa and is what locals call the “country.” You won’t find a Target or Costco up there. But you will find gorgeous beaches (only swimmable in the summer), and sleepy little surf towns. The only resort on the north shore is Turtle Bay and it’s lovely. There are some condos situated in the Turtle Bay resort area.

Villas at Turtle Bay: Clustered around the main resort, these villas and condos are the perfect blend of the resort amenities (beaches and resort shops and restaurants) and the added comforts of a vacation rental (kitchen, laundry, etc.) Find specific condo units here.

Kuilima Estates: A bit further away from the resort and beach, this property is still very convenient with a beautiful location. Find specific condo units here.

Best Condo Complexes on Maui

Trying to find the perfect place to stay on Maui is tricky, and if you’re trying to narrow down all of the different condo options, it can be downright mind boggling. I’ve made recommendations for specific condo units in this post (mostly budget options), but availability, seasonal pricing, or other factors may leave you still needing more options.

In this post, I’m breaking down 50+ condo complexes (also called condo-tels or condo resorts) by area on Maui that are good places to stay. Most of these are beachfront with great locations. I’ve also got extensive descriptions of each area so you can figure out what’s most appealing to you.

I think the best place to find (and book) Maui vacation rentals is Vrbo. They’ve been around forever and are probably the most reputable booking platform online (with owners and vacationers alike), which means that you’ll find more quality properties listed on Vrbo than anywhere else online. I used to book more often with Airbnb, but I’ve begun to find that they often don’t have what I’m looking for (especially when I want to book a condo/unit within a resort property).

So all of the condo complexes I will be linking to are bookable within Vrbo.

Disclaimer: This is by no means an exhaustive list of every condo complex on Maui. There are soooooo many, and there likely are some that aren’t on this list that are perfectly good places to stay at. I’ve compiled this list largely based on location, ratings and reviews, and an overall vibe of what I’m looking for in a place to stay.

West Maui

Most people stay in West Maui, if for no other reason than it’s where the majority of the resorts and condos are. West Maui is home to Maui’s original resort areas (when tourism development began in the 1960s) and it’s still where most of the tourists flock today. West Maui is usually sunny and dry, making it perfect beach weather. Also, there’s a wide range of accommodation options so whether you’re looking to splurge on a beachfront resort or save on a condo, you can find it in West Maui. There’s also a lot development, so if you’re the type that likes to be in the middle of the action, West Maui is where it’s going on. West Maui is actually one of the prettiest parts of Maui, with the jagged green mountains rising up in the background offering some amazing hiking trails, it also has some of the best beaches on the island. Accommodations on the west side stretch from Lahaina town (although the whole area is often referred to as Lahaina) all the way up to Kapalua with Ka’anapali Beach and the Napili area in between. Drive time from the Kahului airport (OGG) to the Lahaina area is about 45 minutes.

Lahaina: Lahaina (an old whaling village turned tourist hot spot) is where many choose to spend a lot of their time (especially evenings) on Maui. Although not many accommodations right in Lahaina town, it’s the hub of activity for the west side. Front Street is packed with shops and restaurants (many offering ocean views) and has a nice vibe that makes it a “hang out” spot for people in the evenings. The docks in Lahaina are also where a lot of the water excursions leave from (whale watching, glass bottomed boats, submarines, and ferries to Lanai). Lahaina is a short drive away from Ka’anapali Beach, Napili, and Kapalua so you don’t necessarily have to stay right in town to take advantage of the amenities.

Lahaina Shores Beach Resort: Just a short walk from the heart of Front Street and Lahaina Harbor, the Lahaina Shores Beach Resort is the only beach front condo resort within walking distance to town. If you don’t have a car, this is your best option. Find specific condo units here.

Aina Nalu by Outrigger: Not located on the water, but just a block or two from Front Street, this updated property has a swanky feel and a nice pool. If you want close proximity to town, but don’t care about being on the sand (or water for that matter), this is a great pick. Find specific condo units here.

Ka’anapali: Maui’s famous Ka’anapali Beach is a few miles north of Lahaina and although it comes nowhere near it in terms of crowds, I would call it the Waikiki of Maui. Fronting it are the big name resorts you would expect (Sheraton, Westin, Marriot, and Hyatt to name a few) plus a few condo resorts. There’s also a nice outdoor mall with plenty of shopping and dining right on the beach. The three-mile beachfront promenade makes it easy to get around and it seems like there’s always something to do. Catamarans pull right up to the beach to take passengers out on snorkeling excursions and there’s good snorkeling at the far north end at Black Rock. This stretch of beach is my top pick for a location on west Maui.

Ka’anapali Ali’i Resort: Sitting on a prime spot on Ka’anapali Beach next to the Westin, this is probably the best spot if you want a phenomenal location and great pool complex for a deal. Find specific condo units here.

The Whaler: Right next to Whaler’s Village (the shopping and dining complex that anchors the area), the Whaler’s has a nice collection with condos. The grounds are lovely, but the pool is primitive if that’s a necessity. Find specific condo units here.

Ka’anapali Maui at the Eldorado by Outrigger: Located in the Ka’anapali Resort area, this property looks out over the golf course, but it’s still nearby the beach and your daily resort fee covers amenities such as a golf course shuttle, BBQs, and a private cabana area on the beach. Find specific condo units here.

Where to Stay in Maui

If you’re planning a trip to Maui and wondering where to stay, this post is for you! If you’ve never been before, you might be overwhelmed…which part of the island should you stay on? Are some beaches better than others? Are those fancy resorts really worth the money? Will a condo save you big bucks? I’m going to let you in on everything you need to know!

Lay of the Land, Maui Style

Maui is kind of a big island (we’re talking 10-12 hours of solid driving to go all the way around, which is just a point of reference because NOBODY drives around the entire island in a day) so don’t underestimate its size when you’re planning your trip. It’s divided into four main regions (West Maui, South Maui, East Maui, and the North Shore/Upcountry area) but only has two resort areas (on the west and south shores).

You’ll fly into Kahului Airport (OGG), which is located on the north shore in the valley between the two mountains (Haleakala to the east and the West Maui Mountains to the west). This is where Wal-Mart, Target, Costco, and Whole Foods are located, but you likely won’t spend much time in Kahului once you pick up your rental car and groceries.

West Maui: West Maui was originally developed in the 1960s and remains the most popular place to stay and play on Maui. The old whaling village of Lahaina anchors this area and the Ka’anapali resort area is home to the majority of dining and accommodation options on this side of the island. Drive time from the Kahului airport (OGG) to the Lahaina area is about 45 minutes.

Most people stay in West Maui, if for no other reason than it’s where the majority of the resorts and condos are. West Maui is home to Maui’s original resort areas, and it’s still where most of the tourists flock today. West Maui is usually sunny and dry, making it perfect beach weather. Also, there’s a wide range of accommodation options so whether you’re looking to splurge on a beachfront resort or save on a condo, you can find it in West Maui.

There’s also a lot development, so if you’re the type that likes to be in the middle of the action, West Maui is where it’s going on. Lahaina (an old whaling village turned tourist hot spot) is where many choose to spend their evenings. Front Street is packed with shops and restaurants (many offering ocean views) and has a nice vibe that makes it a “hang out” spot for people in the evenings. The docks in Lahaina are also where a lot of the water excursions leave from (whale watching, glass bottomed boats, submarines, and ferries to Lanai) so if you’re planning to do much of that, it’s nice to be staying nearby.

Maui’s famous Ka’anapali Beach is also in West Maui (just north of Lahaina) and although it comes nowhere near it in terms of crowds, I would call it the Waikiki of Maui. Fronting it are the Sheraton, Westin, Marriot, and Hyatt to name a few. There’s also an outdoor mall with plenty of shopping and dining right on the beach. The three-mile beachfront promenade makes it easy to get around and it seems like there’s always something to do. Catamarans pull right up to the beach to take passengers out on snorkeling excursions and there’s good snorkeling at the far north end at Black Rock.

If you’re looking for something quieter, Napili Bay and Kapalua Bay to the north might float your boat. Napili Bay (a great beach) is surrounded by older condos and small inns or resorts that although they’re showing their age are still pretty charming (and you can’t beat the location)! For more of a luxury resort feel, try Kapalua (the name of a beach, but also a resort area). It’s centered around golfing, but the Montage and the Ritz Carlton are some of the swankiest places around and although you’re not far from Lahaina and Ka’anapali, you’ll feel a world away. There are also a bunch of fancy-schmancy condos in Kapalua.

West Maui is actually one of the prettiest parts of Maui, with the West Maui Mountains rising up in the background offering some amazing hiking trails, it has some of the best beaches on the island (if you don’t mind the crowds) and you’re close to the famous Honolua Bay and all that’s going on in Lahaina and Ka’anapali.

Molokai: The Most Hawaiian Island

This trip to Molokai was sponsored by Maui Nui (the tourism board for Maui County), which means all of my expenses were paid for and the itinerary was organized for me. As always, I only recommend my absolute favorites to you. Thank you for supporting the brands that make Hulaland possible.

After spending four days on the Hawaiian island of Molokai (often called the most Hawaiian of the Hawaiian Islands), I feel more aware and appreciative of Hawaii and its culture than ever before. Countless trips (and even a brief time actually living in Hawaii) didn’t expose me to the type of uniquely Hawaiian experiences that I was able to participate in during my short time on Molokai.

As a visitor, I’ve never so fully experienced “aloha” anywhere else in Hawaii. Aloha isn’t the waterfalls. It’s not the beaches or the rainbows or the lush green mountains. It’s not the scent of plumeria wafting over you while you relax in a hammock. Aloha isn’t a mai tai. Aloha is the spirit of the people. And there’s nowhere in Hawaii that a visitor is embraced more fully with aloha than Molokai.

After about my second day on Molokai, I realized that the things I was learning, seeing and experiencing on Molokai were all connected to the people of Molokai. Unlike other places in Hawaii where I remember “things I did,” my memories on Molokai are of the people I met. Every experience is connected with a person, sharing their knowledge, their way of life, their culture, and their appreciation for their island.

This is what makes Molokai different than any other Hawaiian Island. It’s what makes it special. Molokai is the fifth largest Hawaiian Island, situated between Maui and Oahu. In the morning, you can watch the sun come up over Maui, and in the evening you can see the lights of Honolulu. But it’s a world away from either island.

What You Should Know Before You Go

How to get there: By air is the only way to get to Molokai (there is no longer ferry service available from Maui). Mokulele Airlines and Makani Kai both offer numerous flights a day to Molokai (MKK) from both Maui and Oahu. The flight is only about 20 minutes and leaves out of the commuter terminal which means no TSA (show up 30 minutes before your flight, no hectic chaos, no rules about liquids, etc.). The planes are small (only 8-9 passengers), but the views are incredible.

Everything is closed on Sundays: Everything. It’s not a good day to arrive on the island, and honestly if you’re only going to be there for a few days, I would schedule it so you’re not there on Sunday.

There are no stoplights: Not one! They just installed a flashing crosswalk light by one of the schools (and I heard it was the talk of the island), but that’s it. This gives you an idea of the size and scope of the island and also how much traffic there is.

Watch out for deer: There are so many deer on Molokai, especially out towards the west end so be very careful when driving at dusk. Drive slow!

Everybody knows everybody: Unlike the other Hawaiian Islands where there’s such an influx of transplants and newcomers, Molokai is an extremely tight knit community. So tight knit that if they don’t know you, they know you’re a visitor. But everyone is so friendly and welcoming! So many times walking through town people would stop and ask me where I was from and how I was enjoying my stay. That just doesn’t happen anywhere else. It was also fun when with our tour guides to see everyone greet everybody when we went into a store or restaurant. If you’re from a small town where everyone has known you since were a child, you’ll be familiar with the vibe. If you’re not, it’s neat to see firsthand.

This is “old Hawaii:” Compared to the other islands, Molokai is incredibly undeveloped. This of course, is part of its charm, but it can also pose some logistical challenges if you’re visiting. There are a couple small grocery stores and markets, but don’t expect a Target, Walmart, or Costco. There are plenty of restaurants, but nothing too fancy. You’ll have everything you need on Molokai, but it’s good to go in with the right expectations.

How Long Should You Spend on Molokai?

Molokai has a reputation for being boring or having nothing to do. By the time you finish reading this post, hopefully I’ll have debunked that myth but it still doesn’t compare to the four main Hawaiian Islands. I think three days is the perfect amount of time to visit Molokai, and while I don’t normally recommend spending so little time on an island because of travel time, the short flight here plus not having to go through TSA means that you have most of your travel days free. I would recommend a day for touring Kalaupapa, a day for the Halawa Valley, and either spending a day with Molokai Outdoors (if you haven’t used them for day 1 or 2) or spending a day filling in with what interests you.

I also recommend sandwiching in your time on Molokai in the middle of your trip. For example, I wouldn’t recommend flying straight to Molokai from the mainland because if your flight to Maui (or Oahu) is delayed, you’ll probably end up missing your connection. Fly to Maui and spend a few days, then hop over to Molokai and end your trip back on Maui for a bit before flying home.

Guide to the North Shore, Maui

Home to big wave, surfers, hippy towns, and so many sea turtles, Maui’s north shore is a region that you definitely don’t want to miss. Even if you’re staying in the resort areas in south and west Maui, it’s worth at least a day trip to see the sites.

There are three main towns/areas that make up the north shore: 1) Paia: right on the beach, this surf town is packed with shops and restaurants 2) Haiku: located further up in the jungle, Haiku is more off the beaten path for tourists, but there’s still quite a bit to see and do 3) Haliimaile: not really a town, but an old pineapple plantation, if you blink you’ll miss it!

So here’s a rundown on what to do, where to eat, and where to stay (if you decide you’re interested in more than a quick day visit):

Things to Do

Hang out in Paia town: This “hippy” town on the North Shore has some of the best shopping and dining on Maui. It’s laid back vibe makes it feel more local than other parts of Maui but it has all of the amenities that make it a fun place to spend the day. Great local boutiques and plenty of diverse restaurants all a stone’s through from beautiful Baldwin beach are a great reason to make the trip up to Paia from your resort. Make sure to stroll up Baldwin Avenue to see the colorful surfboard wall in from on the Maui Aloha Hostel.

Maui Pineapple Tour: Book a tour of the small plantation that produces the Maui Gold pineapples. It’s WAY more authentic than the Dole Plantation on Oahu and you can also combine it with lunch at the Haliimaile General Store across the street and a tour of the Haliimaile Distillery. I recommend booking the morning tour for the coolest weather.

RELATED: Not very familiar with Maui? Read up on the lay of the is(land) and where to stay plus my favorite beach resorts, budget hotels, condos, honeymoon resorts, family friendly resorts, luxury resorts, and boutique hotels plus my area specific guides (including where to stay, eat, and things to do) for Wailea, Ka’anapali, the north shore, and upcountry plus my review of staying at the Four Seasons Maui.

Bike the Volcano: One of the most popular tourist attractions on Maui is Haleakala, a large dormant volcano, and while tons of people ascend to the summit each morning to watch the sunrise, the lucky ones get to follow it up with a downhill bike ride from summit to sea. It’s a bucket list adventure and most companies (my favorite is Maui Sunriders) have their headquarters (where you’ll end your tour) in Paia or Haiku. Read all about biking the volcano here.

Baldwin/Baby Beach: Right in Paia town, this gorgeous white sand beach is usually too rough for swimming, but it’s fun to watch the wind and kite surfers. But the far west end of Baldwin beach has a protective shelf that makes for good swimming conditions plus a strong current if you get further out that makes for a good resistance pool. It’s called “Baby Beach” and on a good day (sunny, no wind) it’s packed with local families.

Ho’okipa Beach: Ho’okipa beach is a resting area for the Hawaiian green sea turtles. Every afternoon they will swim up onto the beach (the far East end) to sun themselves while they nap. A volunteer group has taken it upon itself to protect the turtles by enforcing a perimeter around them, but this is the perfect spot to see a whole herd of turtles (usually around 20) both in and out of the water. Ho’okipa is also a popular surfing beach and on good days you’re guaranteed a show from the outlook where there are usually at least a couple of food trucks parked.

Staying at the Four Seasons, Maui

On my latest trip to Maui, (a girl’s trip with my friend who had never been before) I scheduled a lot of spectacular activities like driving the road to Hana and going up for sunrise at Haleakala. Spectacular, but exhausting. After all of that adventuring, we knew we wanted some time at the end of our trip to unwind with a little luxury. Nobody does luxury like the Four Seasons, so we booked a three-night stay at the Four Seasons Maui in Wailea.

In this post, I’m going to share a travelogue of my stay at the Four Seasons Maui, give you a list of things to do there, and finish up with tips for enjoying your stay.

The Four Seasons Maui is located on Wailea Beach in south Maui. Beautiful, sun drenched Wailea is home to some of the best high-end resorts on Maui and with that comes excellent shopping and dining.

We checked into the Four Seasons on a Monday morning, but the Four Seasons experience really begins before check in. Once we booked, we downloaded the Four Seasons app, and a concierge team member was in communication regarding our stay…mostly to know when we’d be arriving and offering to set up transportation.

Since we were already on island and just changing accommodations, we checked in about 10:30 and were greeted with fresh flower leis, ginger mint lemonade, and chilled lavender towels.

Our room wasn’t quite ready, which we expected, and we had already discussed how to jockey bags so we could find a place to change into suits and hit the pool. But the Four Seasons had a plan for that. They whisked all of our bags away to the “Aloha Suite,” a full suite with showers, lockers, changing rooms, a lounge, a fridge with bottled water, and plenty of charging stations. In less than 15 minutes, we had changed, packed away our clothes, and dug out the beach bags and what we wanted to take with us for the day. We called the bellman back (they had showed us how to reach them on the house phone), and we headed to the pool. Having only been on property for about 30 minutes at this point, I felt like I was already experiencing the world class service the Four Seasons is famous for.

With coverups and hats on and beach bags in hand, we headed out to explore the property and stake out a spot for the afternoon. We settled at the adults only “Serenity Pool” which has got to be one of the best infinity pools on Maui. By 11 AM it was hopping and we could only find a place in the sun. Well let me rephrase that. The attendant only had spots available in the sun. Because one doesn’t search for a chair at a Four Seasons pool, you check in with an attendant and they get you all settled in. It’s nice.

10 Condos on Kauai Under $100/Night

The most difficult part of planning a Hawaiian vacation for me is deciding where to stay. While I love luxurious beach resorts as much as the next girl, most of my trips to Hawaii tend to be pretty active (especially Kauai!), and it just doesn’t make sense to pay an arm and a leg to stay at a fancy place when I’ll be spending most of my days hiking in Waimea Canyon or boating down the Napali Coast. But…sometimes I like a little more comfort than a budget hotel provides. Luckily, I’ve figured out the perfect way to save some cash and still get amazing amenities by staying in a condo or vacation rental!

Hawaii has a great variety of accommodation options, which makes it the perfect place to try out a vacation rental. Since Hawaii is a major vacation destination, there are of course MANY condos to choose from but besides condos, Hawaii has a ton of “ohanas.” Ohana means family (any Lilo and Stitch fans out there???) and in Hawaii the term is applied to separate living units located on the same property as the main house. Many homes in Hawaii are divided up into multiple spaces (each with its own private entrance, bathroom, kitchenette, etc.) while some have a guest cottage on the property. Because so many homes are configured this way, it’s easy to find a private apartment or cottage on the same property with a local host.

There are several ways you’ll save money on a trip to Oahu by staying in a condo or vacation rental. The biggest way you’ll save money is that it’s soooo much cheaper than staying at a resort or hotel. On many islands you can find condos or ohanas either right on or just a block or two from the beach. Plus, resorts can get expensive really fast if you have more than two adults staying in a room. Rental units are perfect for larger parties who can rent an entire house or multi bedroom condo and split the cost. Another big benefit that rentals offer is the full kitchen (or kitchenette depending on what you book). Having a place to cook some meals and a fridge to store snacks and drinks can really save you a lot.

What should you look for in a vacation rental?

Before you start looking around for specific condos or rentals, it’s best to have a general idea of where you want to stay. If you’re not very familiar with Kauai, you should read this post to get the lay of the is(land) and decide which area you’d most like to stay.

Consider what you need. What’s important to you? Are you looking for a specific location near a certain beach or resort area? Do you need a full kitchen? Reliable Wi-Fi? A full house or just studio? Be clear about what you want before you start searching.

9 Condos on Oahu under $100/Night

A trip to Hawaii can be a once in a lifetime experience, but wow can it be hard settling on a good place to stay! If you’re on a budget and trying to avoid paying resort prices, or you’re just looking for a little something different (maybe a more local experience?) then a condo or vacation rental on Oahu is perfect for you!

What should you look for in a vacation rental?

Before you start looking around for specific condos or rentals, it’s best to have a general idea of where you want to stay. If you’re not very familiar with Oahu, you should read this post to get the lay of the is(land) and decide which area you’d most like to stay. But before you start looking, you should know that by far the bulk of accommodations are located in Waikiki (a neighborhood of Honolulu), and Oahu just passed legislation that limits the rentals in “local” parts of the island. More on that below.

Read reviews. Before you even consider staying at a property, you should read up on what people who have stayed there have to say. Remember, you’ll only hear the good points from the host but reviews usually give a much more honest story. And when I’m weeding through listings, I also put a lot of weight into the photographs provided. If the photos look professional, it probably means that the owner runs their vacation rental in a professional manner and that is a indication that it’s a good place to stay.

Ask plenty of questions. When you’re seriously considering staying at a specific property, you should correspond with the owner and ask them any questions you may have.

Count the extra costs. Be sure to factor in any security deposits, cleaning fees, and booking fees.

Know the cancellation policy. Each property and owner may have different terms so know what they are before you commit.

Where to Stay

Lay of the Land, Maui Style

What should you look for in a vacation rental?

What should you look for in a vacation rental?

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