destinations

Where to Stay in Hawaii

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If you’re planning a trip to the Big Island of Hawaii, you’re in for a great time. It’s not the island that most first time visitors to Hawaii choose to visit (most favor Oahu or Maui) and it’s usually because they’re intimidated by its size (you really can’t see the entire island from one central location). Actually, all of the other Hawaiian Islands could fit inside the Big Island TWO TIMES. This is of course why they call it the Big Island. So yes, it can be overwhelming but the Big Island is home to some of the most spectacular sites in the world (the world-not just Hawaii) so it’s a shame to skip it just because the logistics are tougher to figure out. So here’s what you need to know to figure out where to stay in Hawaii:

The island is divided into two sides: Kona side and Hilo side.
The vast majority of visitors stay on the Kona side even though some of the island’s best attractions are on the Hilo side.
It’s a Big Island so while it is possible to stay on one side and drive back and forth to the other, it means a LOT of time in the car so if you want to see the whole island, you should consider staying in at least two places.

Side note: After you read up on the lay of the is(land) and know which part you want to stay on, check out these posts for MORE recommendations:

Big Island condos under $100/night

7 Big Island budget hotels

10 Big Island beach resorts

6 best family friendly resorts on the Big Island

5 best Big Island honeymoon resorts

Top 10 luxury resorts in Hawaii

12 favorite boutique hotels in Hawaii

Here’s an overview of the island broken down by area:

Kona Side

Kona side refers to roughly the entire West side of the island, including the town of Kailua-Kona (often referred to just as “Kona.” This is the dryer side of the island (no lush jungles or rainforests here) and it’s mostly barren lava fields as far as the eye can see. But no rain also means the best beaches (the vast majority on the Big Island are found on the Kona side) and therefore all of the resorts and condos. This side of the island is mostly made up of:

Kailua-Kona

This is where the main airport is and it’s a good home base for exploring this side of the island. There aren’t many beaches in Kona but you will find a lot of budget accommodation options. You can easily drive to beaches located north and south of town and you’ll be close to most of the island’s cultural and historic sites. You can also easily daytrip to the Pololu and Waipo valleys from here. One of the downsides of staying in Kona is how touristy it is. This is where the cruise ships dock so you can imagine what that entails but on the upside there are a lot of shopping and dining options.

Courtyard by Marriott King Kamehameha’s Kona Beach Resort: This casual beachfront hotel next to the Kamakahonu National Historic Landmark has a nice picnic area, two restaurants, a coffee shop, and a beautiful outdoor pool. Click here to check rates and availability during your stay.

Where to Stay in Kauai

If you’re planning a vacation to Kauai then you’re one lucky dog! It’s one of my favorite Hawaiian islands and probably the prettiest one at that. If you’re very far into the planning process, you’ve probably realized that picking the right place to stay is likely the trickiest (and most important) things you’ll have to do. Where you stay on Kauai can make or break your vacation and there are soooo many options that it can be overwhelming. Not to worry! I’m going to break it down for you, give you an overview of the island.

Side note: After you read up on the lay of the is(land) and know which part you want to stay on, check out these posts for MORE specific recommendations:

7 Kauai budget hotels

12 Kauai beach resorts

Kauai condos under $100/night

5 Best Family Friendly Resorts on Kauai

5 best Kauai honeymoon resorts

Top 10 luxury resorts in Hawaii

12 Favorite boutique hotels in Hawaii

Here’s everything you need to know about where to stay in Kauai:

Lay of the Land

Kauai is divided into four major sections (North Shore, East Shore, South Shore, and West Shore). Each section has its pros and cons and own individual personality. Depending on what you’re looking for and what’s most important to you (budget, convenience, stellar views, beautiful beaches, luxury resorts, etc.) one area of the island may be more desirable. Here’s a breakdown of Kauai’s four main areas:

North Shore

In my opinion, the north shore of Kauai is the most gorgeous place on the planet. It has beautiful beaches and the lush green mountainous landscapes that most people’s Hawaiian dreams are made of. As you might guess, it’s so lush because it rains more here than other parts of the island (especially in the winter). The north shore is home to the charming little surf town of Hanalei and some pretty spectacular luxury accommodations. While it’s stunningly gorgeous, it’s also a bit remote if you’re planning on exploring sites on the south and west sides of the island.

Stay on the north shore if…

You want beautiful beaches with gorgeous backdrops.
You want luxury accommodations.
You’re a golfer.

My favorite properties on the north shore:

Princeville Resort: If you’re honeymooning on Kauai during the summer months (roughly April to October) there’s no place better than the Princeville Resort. It’s located on Kauai’s stunning north shore which is without a doubt the prettiest part of the island (although it rains a LOT in the winter months). The pool here boasts the BEST view of any resort in Hawaii hands down, and the luxe vibe is perfect for a honeymoon. Pricing starts at $405/night. Click here to check pricing and availability during your stay.

Hanalei Colony Resort: If you really want to get away from it all, this beachfront hideaway on Kauai’s lush north shore is the place to do it. You won’t find televisions or phones here but you will find plenty of natural beauty. Click here to check rates and availability during your stay.

Hanalei Bay Resort: This fabulous resort tucked away on Kauai’s secluded north shore, has a fabulous pool area, gorgeous beach, and even tennis facilities. It’s also a popular spot for destination weddings. Click here to check rates and availability during your stay.

East Shore

The east shore is often referred to as the “coconut coast” and is the most developed part of the island. This is where you’ll find the most reasonably priced accommodations and it central location makes it a convenient location from which to explore the north and south shores. There are of course lovely beaches on the coconut coast (hello, this is Hawaii!) but you won’t find any awe inspiring backdrops as you will on the north shore and the amenities are usually not as convenient as those on the south shore. You’ll find more “local” beaches on the east side.

Stay on the east shore if…

Budget is the deciding factor.
You want a convenient home base from which to explore the island.

My favorite properties on the east side:

Kauai Marriott Resort: I think the Kauai Marriott Resort is the best “bang for your buck” beach resort on the island. It has one of the largest pools in Hawaii, a golf course nearby, and a full service spa. Starting at $215/night, the Kauai Marriott Resort is definitely a bargain. Click here to check rates and availability during your stay.

Kauai Shores: I stayed at Kauai Shores on my last trip to Kauai and I LOVED it! It’s easy on the budget but the rooms and common spaces are bright and airy, the onsite restaurant is amazing, and it’s right on the beach! It’s location on the east side of the island makes it perfectly situated for exploring both the north and the south shores. Pricing starts at $109/night. Click here to check pricing and availability during your dates.

Courtyard Kauai at Coconut Beach: Located right on the beach on the east side of Kauai, the Courtyard Kauai is a good option for families who need more space to spread out. There are a variety of suites available. The pool area and grounds are beautifully landscaped and maintained and there’s a game room for families to enjoy together. Pricing starts at $230/night. Click here to check pricing and availability during your stay.

South Shore

Kauai’s south side is the driest and sunniest part of the island, which makes it very popular with tourists. There are plenty of big resorts so you’ll find plenty of shopping and dining options. You’ll also find a nice selection of beaches but expect them to be more crowded than beaches on other parts of the island. The south side is a convenient place from which to explore the west side (Waimea Canyon and Polihole beach) but not so convenient for seeing north shore sites.

Stay on the south shore if…

You want sunny and dry weather.
You like a resort feel.
You want a lot of dining options.

My favorite properties on the south shore:

Grand Hyatt Kauai: The Grand Hyatt Kauai is the flagship place to stay on the south shore and it’s perfect for families or anyone wanting a “big resort” experience. Click here to check rates and availability during your stay.

Ko’a Kea Hotel and Resort: Ko’a Kea is located on Kauai’s best beach (in my opinion) in sunny Poipu. If you’re visiting Kauai during the winter months, this is probably the best place on the island to stay. It’s luxurious and swanky and it’s well situated for day trips to Waimea Canyon and the north shore. You’re also likely to see turtle and Hawaiian monk seals basking in the sun just steps from the resort. Pricing starts at $449/night. Click here to check pricing and availability during your stay.

Sheraton Kauai Resort: Located on what I think is the best beach on Kauai (Poipu beach) where finding turtles or Hawaiian monk seals sunning themselves in the sand is a common sight, you can’t go wrong with staying at the Sheraton. The pool is just steps form the sand and there are cabanas available for rent if you want a break from the sun. The resort also has a daily activity schedule with things like lei making, hula and ukulele lessons, island crafts, and water sport demos. Pricing starts at $230/night. Click here to check pricing and availability during your stay.

West Shore: The west shore is definitely the least visited part of Kauai (except for visitors to Waimea Canyon) and not very many people stay here. It’s very barren, dry, and isolated, and not convenient to seeing the rest of the island. Really the only people who are going to be staying over here are hikers and backpackers and people wanting to get away from it all.

Stay on the west shore if…

You’re planning to do hikes on that part of the island.
You want to spend a lot of time at Polihale beach.

RELATED: 15 Things to Do on Kauai

How to See the Napali Coast

Where to Eat on Kauai

Where to Stay on Oahu: Waikiki or Not?

Oahu is Hawaii’s most visited island (largely because it’s home to the state’s capital, Honolulu, and its major tourist hub, Waikiki). Waikiki (a beachfront neighborhood in Honolulu) is home to about 95% of the island’s hotel rooms, so by default, it’s where most tourists end up. Waikiki is basically a big city on the beach. Think endless high rises, flashy shopping centers, all the major chain restaurants, and a million people. All of the major hotel chains are represented as well as plenty of budget options and even trendy new boutique hotels.

And then there’s the rest of the island. So the big question is…to stay in Waikiki or not?

Psst…once you finish reading this post and have a better idea of where you might like to stay, read these posts for MORE specific suggestions:

Oahu Condos Under $100/Night

7 Best Oahu Condo Complexes

10 Oahu budget hotels

12 Oahu beach resorts

5 Best Family Friendly Resorts on Oahu

5 best Oahu honeymoon resorts

Top 10 Luxury Resorts in Hawaii

12 Favorite Boutique Hotels in Hawaii

Guide to Ko’olina (Oahu)

Staying at Aulani, a Disney Resort and Spa

Why You Might Like Waikiki

So…if it’s so crowded, why do people stay there? Simple. It’s Hawaii’s oldest resort area (the Moana Surfrider was built in 1901), and people have been flocking there ever since. It’s also a really beautiful beach with stunning views of Diamond Head in the background. Most people who have never been to Hawaii end up in Waikiki, usually because flights to Honolulu are cheaper than the other islands, and because they’ve heard of it. They think, “it’s popular for a reason…it must be where you’re supposed to go.”

Here are a few more reasons why people like staying in Waikiki:

You can find cheap hotels. Just like any major city, the more hotel rooms there are, the more competitive prices are.
You don’t need a car. Shuttles are a dime a dozen from the Honolulu airport to Waikiki and most visitors just stay in Waikiki/Honolulu and don’t venture out to the rest of the island.
Waikiki is pretty densely populated with attractions (museums, historic and cultural sites, the zoo and aquarium, etc.) so most of it’s easily walkable.
There’s a good (and reasonably priced) trolley system around Honolulu/Waikiki and Oahu has a decent public bus system for getting around to some of the major tourist attractions.
There’s a LOT of shopping. From luxury designer brands at the Ala Moana to major chain stores at the Royal Hawaiian Center, to cheap souvenir outlets everywhere, Waikiki is a shopper’s paradise.
There are a ton of restaurants. You’ll find major chains (Cheesecake Factory, Hard Rock Café, etc.) and pricey resort restaurants as well as local joints (as you venture away from Waikiki into Honolulu).

Why You Might NOT Like Waikiki

Now, a few reasons you may not like Waikiki:

It’s very crowded. On the beach, you’ll be shoulder to shoulder with fellow sun worshipers.
There’s soooo much traffic! Even if you have a car and you’re willing to get out and explore, expect a headache getting around.
There’s so much to see on the island besides Waikiki (the truly beautiful parts!) and getting around by bus isn’t too convenient.
If you do rent a car, many Waikiki resorts charge as much as $40/day to park it.
You may come home feeling like you’ve had more of a city vacation instead of an island vacation.

Best Condo Complexes on Oahu

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.

5 Maui Day Trips

If you’re planning a trip to Maui (maybe you’ve already been before and this is a repeat trip?), you’re likely looking forward to plenty of time beach bumming and doing your favorite things, but just in case you’re looking for even MORE things to do and fun to be had, consider one of these 5 day trips from Maui:

25 Things to Know Before You Go to Maui

1. Maui is the second youngest of the Hawaiian Islands. It was created by a volcano almost 1.3 million years ago. It’s also the second largest of the four main Hawaiian Islands, and has a population of about 144,000 people.

2. It’s called the “Valley Isle” but it’s a nice mix of natural and developed. Maui hits the sweet spot between Oahu and Kauai. It’s fairly quiet and you’ll certainly find plenty of “country” but you’ll also find high-end resort areas with fine dining, amazing shopping, and top-notch service. Overall, I think Maui will give you the best Hawaiian vacation experience out of all of the islands.

3. Hawaii was the 50^th state added to the United States of America. Despite it being a US state, more than one person has asked me if you need a passport to travel there. You don’t. Also, when referring to the contiguous United States, you don’t call it “the states” like you would when traveling internationally. You refer to it as “the mainland.”

4. It may feel like a different country, but remember, you’re still in the US. Hawaii has a very distinct culture and its location in the middle of the Pacific Ocean often makes it feel like a foreign land, so many visitors question how things are done. Here’s the deal, everything works like it does back home, except when it doesn’t : ) Seriously though, your phone service and everything works exactly like it does at home. But you will find yourself subject to the quirks of “island life.” Things move slower so relax and just go with the flow.

5. The Hawaiian Islands run on the Hawaii-Aleutian Time Zone. Hawaii also doesn’t observe Daylight Savings Time so they’re 3 hours behind West Coast time (6 hours behind East coast time) when we’re on Daylight savings time, and 2/5 hours when we’re not.

destinations

Lay of the Land

Why You Might Like Waikiki

Why You Might NOT Like Waikiki

Lay of the Land, Maui Style

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