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Christopher & Kelsey

Thursday, October 2, 2025 • Maui, HI

Christopher & Kelsey

Thursday, October 2, 2025 • Maui, HI
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Airbnb Condo in Kihei

Picture of Airbnb Condo in Kihei

This Airbnb apartment was our personal favorite stay during our August 2023 trip. One of the best ways to experience Maui in all its glory is to stay at an Airbnb. Airbnb has plenty of incredible and unique options, ranging from gorgeous villas, cool apartments, to retro campervans and the island’s Airbnb's can be found all over its valleys, beaches, and population centers like Wailuku, Kihei and Kula. The cool apartment we stayed at was in Kihei and here are some of the things we noticed.


Pros:

1. Price

2. Distance to Beach/ wedding venue

3. Beach furniture included

4. Free parking


Cons:

1. Pool is subpar


The link below will take you directly to this Airbnb's info. Recommend checking out Airbnb.com as well.

Grand Wailea, A Waldorf Astoria Resort

Picture of Grand Wailea, A Waldorf Astoria Resort
3850 Wailea Alanui Dr, Wailea, HI 96753, USA
(808) 875-1234

We stayed here during our May 2024 trip! This hotel is situated right next to the ocean and public beach. They offer a wide range of activities, amenities, restaurants, pools and even a cave bar. This hotel also boasts the largest and most expensive collection of Hawaiian Art in all of the State of Hawaii. This is also where they filmed one of Chris' favorite comedy movies "Just Go With It," starring Adam Sandler and Jennifer Aniston. We took their free beach yoga classes in the morning, went to the restaurants, and spent the afternoons relaxed in their lazy river and pools. While this hotel has a lot of things to do, it is definitely more on the expensive side.


If value hotels are more your style but you still want to check out some of the nicer resorts, check out resort pass as it allows you to use their amenities without spending $$$ on a room.


Pros:

1. Luxury experience

2. Direct access to polo beach

3. Largest/Best Pools in Maui

4. Part of Hilton Hotels


Cons:

1. Expensive (average room is $800-1100 per night)

2. Parking is $55 to $65 per night at hotel, but can park for free nearby

Hilton Vacation Club Ka'anapali Beach Maui

Picture of Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'Anapali Shores Place, Lahaina, HI 96761, USA
(808) 661-2000

We stayed here during part of our May 2024 trip! While this is technically a timeshare hotel, you are able to book individual hotel rooms for your vacation. This hotel ended up being a great deal as it only amounted to $300 a night including taxes and fees!


Pros:

1. Price

2. Large 1 bedroom fully stocked apartments (800-1000 square feet)

3. Solid amenities like putput golf/standard pool

4. Free parking and within walking distance to some restaurants/food trucks

5. Easy drive to wedding venue and the northern part of the island


Cons:

1. Lack of restaurant availability in direct area

Wailea Beach Resort - Marriott, Maui

Picture of Wailea Beach Resort - Marriott, Maui
3700 Wailea Alanui Dr, Wailea, HI 96753, USA
(808) 879-1922

This was a hotel we stayed at during part of our August 2023 Trip. We were very excited to stay here based on previous reviews and pictures but ended up having a few experiences that put a sour taste in our mouth.


They would not honor Chris military rate for our stay. The representative we worked with was very unhelpful during this process which made the beginning of our stay kick off to a poor start.


Our AC also went out in the middle of the night and room service wasnt answering. We were in the building furthest away from the Lobby so Chris ended up walking 15 minutes to explain to them the issue we were having. Instead of moving us to a new room right away, they told us we needed to wait for maintenance to arrive to see what the issue was. Another hour and a half later of maintenance working on the system, they informed us it could not be fixed and we would have to go back up to the front desk and request a new room.


The hotel is located on the Wailea board walk, which makes it very easy to get around the hotel campus along with walking to other hotels/restaurants/Wailea shoppes.


Pros:
1. Direct access to Ocean and board walk.
2. Beautiful & spacious hotel rooms with views of the water and nearby island of Lanai.
3. Many activities & pools (including two adults only pools)




Cons:
1. You need to book any activities well ahead of time. We tried to book a few activities a month before our stay and everything was sold out.
2. It is a fairly large campus so if you have trouble walking, this may not be the best hotel for you.
3. Many amenities are not free and the hotel included a few hidden fees we were not expecting.
4. Standard rooms are expensive, $700-$1100 per night.
5. Parking is $55 to $65 per night and no free parking nearby.