Where to Stay

13 Vacation Rentals on the Big Island Under $100/Night

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Are you struggling finding the perfect place to stay on the Big Island? Picking just the right spot is usually one of the hardest parts for me when I’m planning a trip. I love staying at fancy beach resorts (pretty much more than anything!), but it just doesn’t always make sense to pay so much money when I’ll be spending most of my days hiking in Hawaii Volcano National Park or visiting amazing colored sand beaches.

So I’ve got the perfect solution for you…you can save a bundle and still get amazing amenities by staying in a condo or vacation rental on the Big Island!

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 the Big Island 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 the Big Island, 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.

How to Find the Best Maui Vacation Rentals

One of the trickiest parts of planning a trip for me is finding just the right place to stay. My trips to Hawaii are pretty active and include plenty of exploring so I don’t want to pay a bundle on a fancy beach resort when I’ll be off trekking to the summit of Haleakala for sunrise or hiking through the bamboo forests of Hana, however sometimes a budget hotel can leave a little to be desired when I’m in the mood to lounge at the beach or poolside.

So I’ve got the perfect solution for you…you can save a bundle and still get amazing amenities by staying in a condo or vacation rental on Maui!

There are several ways you’ll save money on a trip to Maui 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 Maui, you should read this post to get the lay of the is(land) and decide which area you’d most like to stay.

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.

Guide to Ka’anapali, Maui: Where to Stay, Where to Eat, & What to Do

Ka’anapali is a resort area in West Maui that’s anchored by the ultra nice Ka’anapali beach. Originally developed in the 1960s, it remains the most popular place to stay and play on Maui. The old whaling village of Lahaina is nearby so you’ll be right in the middle of the majority of dining and accommodation options on this side of the island. It’s about a 45 minute drive from the airport (in Kahului) to the Ka’anapali resort area.

If you’ve just started researching where to stay on Maui and you’re stuck between whether south Maui (Wailea and Kihei) or west Maui (Ka’anapali/Lahaina/Kapalua) is better, read this post.

Where to Stay

Ka’anapali Beach

Westin Maui Resort & Spa: This is my number one hotel recommendation for families visiting Maui (especially if you want to be on the west side). It’s located right on Ka’anapali Beach (which is great for swimming and snorkeling) next door to the Whaler’s Village, which has a lot of shopping and dining options. There are also snorkel catamarans that pick up right on the beach. The resort has a huge “aquatic complex” with five pools (one for adults only) and a great waterslide. There are parrots and flamingos on the grounds and there’s a kid’s club as well. Pricing starts at $250/night. Click here to check pricing and availability during your stay.

Sheraton Maui: Most Sheraton resorts are pretty family friendly and this one is no different. It’s located on Ka’anapali Beach (just a few doors down from the Westin) right in front of Black Rock (one of Maui’s most popular snorkeling spots). It has a nice pool area and several dining options. You can also walk down the bike path to the Whaler’s Village for shopping and dining. Pricing starts at $240/night. Click here to check pricing and availability during your stay.

Hyatt Regency Maui Resort: This recently renovated resort also sits on Ka’anapali Beach (the opposite end of the Sheraton) and has a lovely pool area and kids club. The real selling point of this resort though are the penguins! Seven African black-footed penguins have taken up residence in the hotel’s atrium lobby and they’re a sight to see! They have feedings every day. Stop by and check them out if you’re in the Ka’anapali area. Pricing starts at $250/night. Click here to check pricing and availability during your stay.

Marriott Ocean Club: The Marriott has a great location on Ka’anapali Beach that will keep you in the middle of the action while still staying at a familiar property (if you track points through Starwood or Marriot, that may be of interest to you). Click here to check pricing and availability.

Ka’anapali Beach Hotel: Located right on bustling Ka’anapali Beach, the Ka’anapali Beach Hotel is the perfect place to stay on Maui’s west side. Located on the Ka’anapali beach walk nearby the Sheraton, Westin, and Hyatt, you’ll enjoy being in west Maui’s gorgeous resort area at a fraction of the price. This charming “old Hawaii” hotel starts at $149/night. Click here to check pricing for your dates.

The Whaler on Ka’anapali: This condo resort is right on the beach and has all of the amenities of the big resorts (nice pool area, gardens, beach rentals) at a fraction of the price with the added bonus of getting much more space. Check individual rentals through Airbnb (use this link for $40 off your first stay) or Vrbo.

Wailea, Maui: Where to Stay, Where to Eat & What to Do

Of all the amazing resort areas in Hawaii, Wailea – a resort community in south Maui – is by far my favorite.

If you’re never been to Maui before, chances are it’s exactly what you think Maui would be like – manicured and lush, quiet and luxurious with gorgeous beaches and world class resorts. It’s definitely not “local,” but it’s the stuff Hawaii vacation dreams are made of. Plus, unlike some resort communities on other islands, Wailea isn’t super isolated. It’s right next to Kihei, a more local town, albeit very touristy, and not a far drive to town (Kahului) or the north shore.

If you’ve just started researching where to stay on Maui and you’re stuck between whether south Maui (Wailea and Kihei) or west Maui (Ka’anapali and Kapalua) is better, read this post. But spoiler, south Maui (Wailea specifically) is my favorite.

Where to Stay

Photo from Thomas Hawk via Flickr.

Four Seasons Maui: The Four Seasons is the granddaddy of them all and definitely my #1 pick for a Maui honeymoon. The resort is super luxurious and it’s located in Wailea which is much quieter (and more upscale) than the west side. The spa, the pools, the restaurants, and the beach…they’re all phenomenal. The only problem with staying here is you probably won’t ever want to leave the resort. Pricing starts at $450/night. Click here to check pricing and availability during your stay.

Grand Wailea: This is my other number one hotel recommendation for families visiting Maui ; ) This is your best south side option. While this is a world class resort for anyone (gorgeous open air lobby, plenty of shops, dynamite spa, amazing dining, and one of the island’s best beaches), it’s especially great for families. The Grand Wailea has one of the best pool complexes on Maui (probably anywhere really). The nine different pools include tons of water slides (they actually just opened a new “lava slide”, a rope swing area, a rapid river, water elevator, hot tubs, a swim up bar, and an adults only pool. The Grand Wailea also has a kids club, a teen club, a gaming lounge, and a ton of cultural activities to participate in. Pricing starts at $350/night. Click here to check pricing and availability during your stay.

Fairmont Kea Lani: The Fairmont Kea Lani is the only resort on Maui that is exclusively suites so you’ll get quite a bit of space for a pretty penny. It’s located on beautiful Polo Beach, which is connected to Wailea beach and Ulua beach via a walkway. Click here to check pricing and availability and read my full review from my latest stay here.

Ko’olina Oahu: Where to Stay, Where to Eat, & What to Do

Ko’olina is an oceanfront resort area on the leeward (west) side of Oahu. It’s a preplanned community (as in, much of the infrastructure was laid out before many of the resorts and restaurants moved in) so it has a bit of a curated and idyllic vibe that although is definitely not “local” Hawaii, is nevertheless heavenly for vacationers. It’s location on the leeward side means that the weather is almost always dry and sunny, and it’s home to some of the island’s loveliest beaches. There are four lagoons in the Ko’olina resort area that are ideal, protected places to swim.

Where to Stay

The Ko’olina resort isn’t that big so narrowing down a place to stay won’t be too difficult.

Aulani, a Disney Resort and Spa: Aulani is the big star around these parts. While being “Disney,” it’s surprisingly the most “Hawaiian” resort I’ve come across in Hawaii. The resort has taken amazing steps to preserve and honor Hawaiian culture and heritage as well as share it with guests. It’s definitely THE place to stay if you have kids. It practically has its own waterpark, and the place has a very comfortable but upscale feel. There’s so much to do at this resort that you’ll constantly be torn between taking advantage of all of the activities and wanting to just lounge around the amazing beach and pools. Read this post for a more in depth review of Aulani. Check rates and read reviews here.

Four Seasons Oahu: If you’re looking for luxury, you’ll find it at the Four Seasons. Recently renovated and converted from a JW Marriott, this property is everything you’d expect from the Four Seasons. With an amazing spa, tennis facility, multiple pools, and yummy restaurants, you’ll be able to pass your vacation here in style. This Four Seasons is considered an entry level Four Seasons property (not quite as lavish and expansive as the resorts on Maui and the Big Island), so if you’d like to experience luxury at a lower price point, this is a great option. It’s usually on par price wise with Aulani. Check rates and read reviews here.

Marriott Ko’olina Beach Club: If you’re a points tracker or loyal to Marriott/Starwood, you’ll definitely want to check out this spot. This gorgeous resort has more pools than you can imagine and wonderful amenities if you’re looking for good bang for your buck. The resort has 1-3 bedroom villas with kitchens so you’ll have more room to spread out. The Marriott is also the only resort on lagoon #3 in Ko’olina (Aulani and the Four Seasons share lagoon #1), so it may seem a little quieter. Check rates and read reviews here.

Ko’olina Beach Villas Resort: If you’re looking for a spacious condo with resort like amenities, you’ll love this place. It’s located on Lagoon #2 and it’s a great option to save some money while still feeling like you’re living it up. You can book your unit through the resort or independently through owner via sites like Airbnb (use this link for $40 off your first stay) or Vrbo.

RELATED: Not very familiar with Oahu? Read up on the lay of the (is)land and where to stay plus my favorite beach resorts, budget hotels, Airbnbs, honeymoon resorts, family friendly resorts, luxury resorts, and boutique hotels.

Vacation Rentals: There’s also a little neighborhood behind the shopping center that’s surrounded by the golf course where you can rent individual houses/villas through Airbnb and Vrbo.

Kapolei: If you’re looking for something even cheaper, expand your search to the nearby town of Kapolei. It’s inland a few miles but still close enough to pop over to the beach and you might find more economical accommodations if you’re just looking for someplace to set up a basecamp to explore the island from.

Staying at the Fairmont Kea Lani, Maui

I received a discounted media rate during my stay at the Fairmont Kea Lani as well complimentary breakfast and cabana rental. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make Hulaland possible.

Wailea, an upscale resort area in south Maui is one of my favorite spots in all of Hawaii. The resorts are fabulous, the beaches gorgeous, and it just feels like 24/7 vacation. On my latest trip to Maui, I spent a few days at the Fairmont Kea Lani (one of the crown jewels of Wailea) soaking up the sun at a poolside cabana, strolling along the beachwalk, and wading through the tidepools on Polo Beach.

The Fairmont Kea Lani is a posh resort located on 22 beachfront acres in Wailea about 30 minutes from Kahului Airport. With a prime spot on Polo Beach at the start of the Wailea Beach Walk, three pools (including a water slide!), numerous restaurants, an award winning spa, and plenty of golf, tennis, shopping, and dining nearby, you’ll be torn between reading and sleeping the day away in a beach lounger and taking advantage of all of the fun!

In this post, I’m going to share a travelogue of my stay at the Fairmont Kea Lani, give you a list of 15 things to do at the resort, and finish up with tips for enjoying your stay.

But first, check out this video of my stay:

My Travelogue

On this trip to Maui, I was lucky enough to be traveling with a couple of first time visitors to Hawaii. There’s nothing better than seeing one of your favorite places through new eyes! We spent the first part of our trip on Ka’anapali Beach and after checking out on the west side and grabbing acai bowls at WowWow Lemonade in Kihei, we checked into the Fairmont Kea Lani.

From the moment we pulled up, it was a first class experience. The portico and lobby are so grand and sweeping, and they perfectly frame the ocean in the distance. We got checked in very quickly, and our room was ready early so we went right up and they had our luggage delivered before we even finished looking around the suite!

I was blow away by the view from the balcony! We had a full on ocean view. While there are a few garden or mountain view rooms, it seems like the resort is laid out so that the majority of the rooms have ocean or partial ocean views.

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, Airbnbs, 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 and Ka’anapali.

The Fairmont Kea Lani is Hawaii’s only oceanfront all-suite and villa resort which makes it a perfect option for families or couples who want more room to spread out. Pricewise, it’s on the lower end of the surrounding resorts in Wailea, but you practically get double the space!

After we got settled, we packed up our beach and pool gear (when you’re staying at a place like this you really only need a bikini, sunglasses, and a book!) and headed out to explore the resort. We settled at the pool near the slide and spent the late morning hours swimming, lounging, and going down the slide!

Once those acai bowls from the morning started to wear off, we went in search for food and ended up at Ama, which is the pool bar and is a similar menu to what the poolside attendants offer. I had a great mahi mahi sandwich and we also tried out one of the cocktails of the day (each day they had a special one at a discounted price).

During our stay, the resort was undergoing some construction which impacted the dining options, but the Makana Market and Café was scheduled to open soon which will give guests the added option of quicker/more convenient food and sundries.

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 specific recommendations:

7 Kauai budget hotels

12 Kauai beach resorts

20 cool Kauai Airbnb rentals

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.

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.

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.

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.

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 specific suggestions:

25 amazing Oahu Airbnb Rentals

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

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.

Where to Stay

What should you look for in a vacation rental?

What should you look for in a vacation rental?

Where to Stay

Lay of the Land

Why You Might Like Waikiki

Why You Might NOT Like Waikiki

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