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Find 5 Star Hotels in Kahoolawe, HI from $414

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Check availability on Kahoolawe 5 Star Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Kahoolawe 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.8 out of 10, Excellent, (1,005 reviews)
"Great location beach and pool. Would stay again."
United States
nicholas gaetano
$743 nightly
The price is $882
Nov 20 - Nov 21
Total with taxes and fees
Grand Wailea Maui, A Waldorf Astoria Resort
A staircase with a view of a garden, palm trees, and a bridge.

2. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,006 reviews)
"Great place to stay with the family."
United States
Iulian
$1,058 nightly
The price is $1,256
Nov 28 - Nov 29
Total with taxes and fees
Fairmont Kea Lani Maui
A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

3. Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,000 reviews)
"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"
United States
Quinn
$1,030 nightly
The price is $1,223
Nov 28 - Nov 29
Total with taxes and fees
Four Seasons Resort Maui at Wailea
A resort with a large pool, a water slide, and a view of the ocean.

4. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
5.0 star property
Wailea
9.0 out of 10, Wonderful, (1,000 reviews)
"Not sure if you can beat the pools, value, location, views, snorkel, and staff on the island! Loved our stay!"
United States
Rachel
$629 nightly
The price is $747
Nov 15 - Nov 16
Total with taxes and fees
Wailea Beach Resort - Marriott, Maui
A poolside area with a fire pit, lounge chairs, and umbrellas.

5. Hotel Wailea Maui

Hotel Wailea Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,003 reviews)
"Spacious and updates rooms with everything you need. The service is simply outstanding. The pool was never crowded. The food at the restaurants was so good!"
United States
Maureen
$814 nightly
The price is $967
Oct 31 - Nov 1
Total with taxes and fees
Hotel Wailea Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

6. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (54 reviews)
"The room was beautiful the view incredible , the amenities were perfect. I would stay again and again"
United States
Risa
$1,899 nightly
The price is $2,254
Nov 18 - Nov 19
Total with taxes and fees
Ho‘olei Villas at Grand Wailea
A spacious living room with a large window, a ceiling fan, a sofa, a coffee table, and a TV.

7. Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (3 reviews)
"This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. "
United States
Mae
Oceanfront Kihei Paradise Vistas
A balcony with a wooden table, a bottle of champagne, and a flower arrangement.

8. 2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (11 reviews)
"Beautifully renovated. Everything you need to enjoy the beach is there for you to use."
United States
Carrie
2 2 Oceanview Modern Resort Vistas
A hotel courtyard with palm trees, outdoor seating, and a view of the ocean at sunset.

9. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
Villa, Garden View, 2-bedroom
A balcony with a glass door, a sofa, a table, and a bottle of champagne.

10. Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Condo was very well stocked and very clean. Thank you for great accommodations."
United States
Shirley
Aloha Chic Penthouse Vistas
A modern kitchen with white cabinets, stainless steel appliances, and a large island.

11. Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (3 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Kahoolawe.
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

575 S Kihei Road Kihei HI
$349 nightly
The price is $414 total per night from Nov 5 to Nov 6
$414 total
Nov 5 - Nov 6
Total with taxes and fees
9.4/10 Exceptional! (418 reviews)
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Kahoolawe Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent
"Ha sido la mejor experiencia"
Edgar 2-night trip
Posted 18 hours ago
Grand Wailea Maui, A Waldorf Astoria Resort

Find out more about Kahoolawe

Ready for an incredible adventure? Add further pleasure on your next trip to Kahoolawe by treating yourself to the best of the best when it comes to lodging. It's an ideal pairing. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Kahoolawe so popular in the last year. There's no reason to delay a getaway to Kahoolawe any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Kahoolawe are the perfect places to relax in when you really need to escape. What are you waiting for?

Get a Great Deal on 5-Star Hotels in Kahoolawe

You'll have a wonderful time at one of these 5-star hotels. High-end restaurants, concierges, and pillow-fluffing are all at the ready. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready for a wonderful adventure. How do you want to relax? A deep-tissue massage to help your cares fall away? A concierge to help you pick out your next adventure? Comfortable beds, lip-smacking main courses, and even spectacular views...these hotels have it all.

Can't wait to get outside? We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Kahoolawe are waiting for you to rest up after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Make Your Escape

The results are in, and Kahoolawe 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. Don't put off your dream vacation any longer. Opt for one of our Kahoolawe 5-star hotels today and settle down in luxe surroundings tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Kahoolawe?
The amount you pay for a 5-star hotel in Kahoolawe depends on factors like when you plan to travel and the length of your escape. An insider tip for scoring an awesome deal? Use our pricing filters to compare the available options for your preferred dates.

  • Search for the lowest price per night from $414

What makes a hotel 5 stars in Kahoolawe?
Exceptional guest service characterizes every 5-star hotel in Kahoolawe. From the minute you step through the door, staff ensure your every need is met, whether recommending activities and tours or providing a nightly turn-down service. Plus, hotels must feature superior amenities to be entitled to a 5-star rating. These can include luxury bathrobes, a wellness center, pools, fine dining kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Kahoolawe?
Our handy filters are the quickest way to find exactly what you're looking for. Select "5-star" and "All inclusive" to see the most upscale hotels in Kahoolawe where your meals, lodging, entertainment and activities are included in the price. At these getaways, your trip is pure extravagance from the moment you arrive.

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