Top 10 Hotels in Kaupo, HI (from $506) 2026 - Competitive Prices

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Our top choices for Kaupo hotels

Hotel

9 outdoor pools, cabanas (surcharge), sun loungers

1. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Katelyn

$786 nightly

Aug 18 - Aug 19

Total with taxes and fees

Kai Ocean View Ali i Suite | View from room

2. Maui Coast Hotel

South Kihei

John

$275 nightly

Aug 21 - Aug 22

Total with taxes and fees

3. Maui Seaside Hotel

Kahului

Patrick

$190 nightly

Aug 31 - Sep 1

Total with taxes and fees

4 outdoor pools, pool umbrellas, sun loungers

4. Wailea Beach Resort - Marriott, Maui

Wailea

chad

$636 nightly

Aug 29 - Aug 30

Total with taxes and fees

5. Hilton Grand Vacations Club Maui Bay Villas

North Kihei

Adolfo

$369 nightly

Aug 20 - Aug 21

Total with taxes and fees

6. Four Seasons Resort Maui at Wailea

Wailea

Ifelere

$880 nightly

Aug 26 - Aug 27

Total with taxes and fees

7. Fairmont Kea Lani Maui

Wailea

Ramy

$1,008 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Residence Inn by Marriott Maui Wailea

Wailea

Christian

$442 nightly

Aug 11 - Aug 12

Total with taxes and fees

9. Maui Beach Hotel

Kahului

Florentino

$217 nightly

Aug 9 - Aug 10

Total with taxes and fees

10. Mana Kai Maui- Official Onsite Rental

South Kihei

Baijumon

$595 nightly

Aug 9 - Aug 10

Total with taxes and fees

5 outdoor pools, cabanas (surcharge), pool umbrellas

11. Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

Anil

$858 nightly

Sep 1 - Sep 2

Total with taxes and fees

12. Hampton Inn & Suites Maui North Shore

Kahului

Christy

$360 nightly

Sep 1 - Sep 2

Total with taxes and fees

13. Gods Peace Of Maui

Makawao

Sarah

$161 nightly

Aug 30 - Aug 31

Total with taxes and fees

Outdoor pool, open 8:00 AM to 9:30 PM, pool umbrellas, sun loungers

14. Aston Maui Hill

South Kihei

Douglas Paul Zwerner or Laura

$341 nightly

Aug 27 - Aug 28

Total with taxes and fees

15. Maui Beach Vacation Club

North Kihei

John L

16. Kohea Kai Hotel Maui

North Kihei

Kalani C F

$197 nightly

Aug 30 - Aug 31

Total with taxes and fees

17. Hana-Maui Resort, a Destination by Hyatt Residence

Hana Town Center

Si Lu

$427 nightly

Sep 1 - Sep 2

Total with taxes and fees

18. AC Hotel by Marriott Maui Wailea

Wailea

Darelys

$434 nightly

Aug 8 - Aug 9

Total with taxes and fees

Outdoor pool, pool umbrellas, sun loungers

19. Courtyard Maui Kahului Airport

Kahului

Leonellie

$339 nightly

Aug 9 - Aug 10

Total with taxes and fees

Economy Condo, 1 Bedroom, Ocean View | View from room

20. Maui Sunset

Central Kihei

Miguel

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Stay near popular attractions around Kaupo

Discover the charm of Kaupo, where outdoor adventures and stunning scenery await. Whether you seek thrilling activities, serene beaches, or romantic moments, the local attractions promise an unforgettable experience for every traveler. Embrace the beauty of nature and create lasting memories in this Hawaiian paradise.

A rugged mountain landscape with a valley and distant peaks under a clear sky.

Haleakala National Park

9.4/10 (1,169 reviews)

Experience the best of adventure and scenery at Haleakala National Park, a stunning destination ideal for nature lovers. With its breathtaking landscapes and outdoor vibes, this national park is about 9 miles from Kaupo, making it an easy addition to your travel plans. Staying nearby allows for quick access to its unique beauty.

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Learn more about Kaupo

Check out Haleakala National Park—just one of the popular sights to explore around Kaupo.

See all hotels in Kaupo

A two-lane road with a white dividing line, surrounded by vegetation and hills in the distance.

Top Kaupo Hotel Reviews

Hana-Maui Resort, a Destination by Hyatt Residence

10/10 Excellent

"There was a delay in our room and we received an upgrade. The front desk was very helpful and pleasant. The bell staff were also so patient and kind. The property is magical and we wish we had stayed an extra night. Highly recommend a stay here instead of doing road to Hana in one day. The tennis and basketball are immaculate! Thank you for having us, we will always remember the great views and spacious property"

Haleakala Sunrise Home, Kula, Maui, Hawaii

8/10 Good

"This is an excellent location for Haleakalā sunrise and also the back road to Hana. I highly recommend leaving early and doing the back road to Hana, it was amazing to have the road basically to yourself until you reach PipiWai Trail. As for the property, it is beautiful and clean and the views are lovely. Delightful hosts. But honestly the setup is a bit odd-you can really hear every little thing the hosts are doing in the kitchen, so it isn’t truly private. Just a flimsy plastic door separates you in the downstairs. And the only available sink is the bathroom sink so if you want to rinse off dishes you use or fill your hiking water bladder, etc, you use the bathroom sink. So it’s a nice place but I wouldn’t stay more than two nights."

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

8/10 Good

"Great stay, perfect location. Research locations to eat before you arrive. Really enjoyed the overall atmosphere of Hana, the people were amazing, and the overall stay was good. Please remember there is no air-conditioning, Wish communication from host was better."

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

10/10 Excellent

"A lovely, spacious property. The 6 of us enjoyed the spacious kitchen and back room for TV viewing and games. The property location was very secluded and provided a very peaceful place to stay after driving the Road to Hana. We had made a late afternoon reservation for Black Sand Beach and were able to check in and drop off our luggage prior to heading to the park. We spent the following day in the National Park (access beyond Hana) and greatly enjoyed our stay. We had two vehicles and their is ample parking available. We did contact the house the morning of departure to let them know a tree had blown down but was thankfully not blocking the drive. They were very appreciative and responsive every time we reached out to them. We would definitely stay here again."

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

10/10 Excellent

"We (3 50'ish siblings and our 88 year old mother) were looking for something other than a condo-farm to stay in on Maui and this house was perfect for that. The sunset views were amazing--you could see down to the ocean on the western side of the house and all the way up to the observatory on Haleakala behind the house. The yard was full of fruit trees--there were goats next door but you could barely see any other houses around. It was wonderfully isolated and quiet.Everything was clean and in working order--as other reviews have said, there are several small steps up/down getting around the house and master bedroom.We were able to use beach towels, cooler, etc. on our day trips.The host met us at checkin to show us around the house and was nearby for any concerns or missing items with a fast response time.Air conditioning was in bedrooms only so the common areas were warmer mid-day (but you could open up several sliding doors to create a pleasant cross-breeze to keep things cooler). We all enjoyed sitting outside in the evenings at the end of long days of exploring.Groceries/restaurants were about a 10-15 minute drive away so convenient.We also enjoyed the location for quicker access to the road to Hana and to Haleakala, while not being too far from beaches/ocean activities."

Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.

8/10 Good

"The property was very well landscaped with lots of interesting plants although there was a fair amount of construction material in the yard and it needed mowing. We didn’t see the owners while there. No cell service and couldn’t get the WiFi to work."

More cheap stays in Kaupo

Hana-maui Resort

5031 Hana Hwy Hana HI

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10/10 Exceptional! (15 reviews)

Hotels in Kaupo with star-rating

Frequently asked questions

When is the best time to go to Kaupo?

The best time to visit Kaupo, Hawaii, is during the dry season, which generally runs from April to October. This period offers the most consistent weather for exploring the area's natural beauty.

During these months, you'll experience less rainfall and plenty of sunshine, making it ideal for outdoor activities like hiking along the coastline or driving the scenic portions of the Piilani Highway. The ocean conditions are also typically calmer, which is great for enjoying the natural tide pools or simply relaxing by the water.

Couples often find this time particularly appealing for a tranquil getaway. The drier weather allows for uninterrupted enjoyment of the secluded beaches and the quiet, undeveloped landscape that makes Kaupo so unique.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Kaupo.

How much is the nightly rate at a Kaupo hotel?

Prices for hotels in Kaupo often vary, but you can find a great deal from $506 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Find hotels in Kaupo, HI from $506

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Our top choices for Kaupo hotels

1. Grand Wailea Maui, A Waldorf Astoria Resort

2. Maui Coast Hotel

3. Maui Seaside Hotel

4. Wailea Beach Resort - Marriott, Maui

5. Hilton Grand Vacations Club Maui Bay Villas

6. Four Seasons Resort Maui at Wailea

7. Fairmont Kea Lani Maui

8. Residence Inn by Marriott Maui Wailea

9. Maui Beach Hotel

10. Mana Kai Maui- Official Onsite Rental

11. Andaz Maui at Wailea Resort - a concept by Hyatt

12. Hampton Inn & Suites Maui North Shore

13. Gods Peace Of Maui

14. Aston Maui Hill

15. Maui Beach Vacation Club

16. Kohea Kai Hotel Maui

17. Hana-Maui Resort, a Destination by Hyatt Residence

18. AC Hotel by Marriott Maui Wailea

19. Courtyard Maui Kahului Airport

20. Maui Sunset

Stay near popular attractions around Kaupo

Haleakala National Park

Learn more about Kaupo

Top Kaupo Hotel Reviews

Hana-Maui Resort, a Destination by Hyatt Residence

More cheap stays in Kaupo

Hana-maui Resort

Hotels in Kaupo with star-rating

Frequently asked questions

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