Photo by Claire Houston

5 Star Hotels in Olowalu, Hawaii

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Check availability on Olowalu 5 Star Hotels

Top Olowalu 5 Star Hotels

Grand Wailea Maui, A Waldorf Astoria Resort
2 bars/lounges, 2 poolside bars, swim-up bar

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1006)
"Spent our honeymoon here, and it was everything we dreamed of and then some! Beautiful views, amazing staff, the ocean! We didn’t want to leave and can’t wait to go back! Thank you to everyone at the Grand Wailea for an amazing time! Mahalo! The Foster’s"
The price is €1,030
includes taxes & fees
1 Apr - 2 Apr
Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1005)
"Very enjoyable experience, we stayed on the Club Level and felt the perks were worth it."
The price is €811
includes taxes & fees
1 Apr - 2 Apr
Four Seasons Resort Maui at Wailea
The Ritz-Carlton Maui, Kapalua
3 outdoor pools, pool cabanas (surcharge), pool loungers

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.2 out of 10, Wonderful, (1008)
"Amazing hotel with amazing service! I left my jackets behind and they FedEx it back to me for free! Thank you."
The price is €1,139
includes taxes & fees
11 Mar - 12 Mar
The Ritz-Carlton Maui, Kapalua
Four Seasons Resort Lanai
Lanai

Four Seasons Resort Lanai

5.0 star property
9.8 out of 10, Exceptional, (213)
"Very good hotel. Recommend for everyone who can afford it)"
The price is €1,350
includes taxes & fees
13 Mar - 14 Mar
Four Seasons Resort Lanai
Sensei Lanai, A Four Seasons Resort
Breakfast, lunch, dinner served; al fresco dining

Sensei Lanai, A Four Seasons Resort

5.0 star property
9.8 out of 10, Exceptional, (126)
"Amazing property - one of the best we’ve ever stayed at!"
Sensei Lanai, A Four Seasons Resort
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor spa tub

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (1003)
"I can’t recommend Hotel Wailea enough! From the moment we arrived to the moment we left, we had an absolutely spectacular stay. Everyone was friendly and accommodating and helpful. The hotel itself is magical. The suites are private and so well equipped and decorated beautifully. My husband loved the fact that he could ask for more cookies on demand. Sometimes it’s the little things. Being an adult only resort was the main attraction for us but once we arrived, we realized there was so much more...
The price is €1,197
includes taxes & fees
30 Mar - 31 Mar
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkelling, surfing

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (195)
"I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open. "
The price is €1,324
includes taxes & fees
10 Apr - 11 Apr
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Outdoor pool, pool loungers

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (39)
"Best property in Maui "
The price is €3,184
includes taxes & fees
5 Apr - 6 Apr
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
View from property

Fairmont Kea Lani Maui Villa Experience

5.0 star property
9.6 out of 10, Exceptional, (5)
"It’s a decent hotel to stay for the family."
The price is €3,339
includes taxes & fees
9 Apr - 10 Apr
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment | Private kitchen

Wailea Luxury Hilltop Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
"We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back! "
Wailea Luxury Hilltop Resort Vistas
Oceanfront Kihei Paradise Vistas
Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, pool loungers

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
Oceanfront Kihei Paradise Vistas
Centrally Located Elegant Vistas
Luxury Condo | Balcony

Centrally Located Elegant Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
"Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!"
Centrally Located Elegant Vistas
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, pool loungers

2 2 Oceanview Modern Resort Vistas

5.0 star property
2 2 Oceanview Modern Resort Vistas
Upscale Luxurious Ocean Resort Vistas
BBQ/picnic Area

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean 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 Olowalu.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI
The price is €1,257 per night from 1 Apr to 2 Apr
€1,257
includes taxes & fees
1 Apr - 2 Apr
9.4/10 Exceptional! (1,006 reviews)
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Trip time! Discover the local cuisine and beaches in romantic Olowalu.

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Photo by Claire Houston
Open Photo by Claire Houston

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Olowalu?
The amount you pay for a 5-star hotel in Olowalu depends on things like when you want to go and the length of your getaway. An insider tip for landing the best deal? Use our pricing filters to check out all of the available accommodation for your preferred dates.

  • Search for the lowest price per night from €701

What makes a hotel 5 stars in Olowalu?
Flawless guest service is the hallmark of every 5-star hotel in Olowalu. From the minute you step through the door, staff attend to your every need, whether answering room service calls 24/7 or providing a turn-down service. What’s more, hotels must feature superior amenities to qualify for a 5-star rating. These can include luxury toiletries, spa facilities, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Olowalu?
Use Expedia’s filter tool to find a luxury getaway in Olowalu where everything you need is included in the price. After your initial search, refine your results for accommodation that have a rating of 5 stars and are listed as “All inclusive.” The most important thing to look forward to at these stays? Pure relaxation and indulgence.
Are there any 5-star holiday rentals in Olowalu?
Our site doesn’t have any 5-star holiday rentals in Olowalu. However, you will still find some top-rated options where the only thing on your itinerary will be to kick back and have fun. See what’s available by searching through our holiday rentals in Olowalu.