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Featured Paia 5 Star hotels

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,511 per night from May 27 to May 28
CA $1,511
CA $1,875 total
May 27 - May 28
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
9.4/10 Exceptional! (1,009 reviews)
"Very happy with our stay and with the staff. All were very friendly."

Reviewed on May 19, 2026

Opens in a new windowFairmont Kea Lani Maui
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
The price is CA $1,317 per night from May 25 to May 26
CA $1,317
CA $1,652 total
May 25 - May 26
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,017 reviews)
"The Grand Wailea is more than grand! You will not regret going there, unless you are a constantly angry, miserable soul. Even then, I believe the Grand Wailea can sweep those miseries away. Is it expensive, yes. Is it worth it, absolutely."

Reviewed on May 19, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
The price is CA $1,175 per night from May 26 to May 27
CA $1,175
CA $1,395 total
May 26 - May 27
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (1,000 reviews)
"Great experience"

Reviewed on May 18, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
The price is CA $1,236 per night from May 22 to May 23
CA $1,236
CA $1,563 total
May 22 - May 23
includes taxes & fees
Book a stay at this luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (1,001 reviews)
"It was a great vacation thanks to the friendly and kind staff. We will definitely return."

Reviewed on May 20, 2026

Opens in a new windowThe Ritz-Carlton Maui, Kapalua
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street Kihei HI
Fully refundableReserve now, pay when you stay
The price is CA $1,098 per night from Jun 15 to Jun 16
CA $1,098
CA $1,385 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (1,003 reviews)
"A hidden gem 💎 beautiful boutique hotel felt very private and secluded. Adults only made the stay very relaxing. Room was well clean and well appointed with amenities and air conditioning. Staff were very responsive overall to requests. Pool and gym both nice and not crowded. Multiple restaurants ..."

Reviewed on May 9, 2026

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle Kihei HI
The price is CA $2,452 per night from Jun 2 to Jun 3
CA $2,452
CA $3,000 total
Jun 2 - Jun 3
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Wailea Beach and Shops at Wailea ...
9.6/10 Exceptional! (46 reviews)
"This was a beautiful villa across the street from the grand wailea. Booking included full use of the resort, which was excellent. Included was a shuttle service with uber-like app that we could use to go anywhere within a 1 mile radius. This was a great stay"

Reviewed on Apr 19, 2026

Opens in a new windowHo‘olei Villas at Grand Wailea
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
2780 Kekaa Drive Lahaina HI
Fully refundableReserve now, pay when you stay
The price is CA $419 per night from May 27 to May 28
CA $419
CA $570 total
May 27 - May 28
includes taxes & fees
Book a stay at this luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Kaanapali Beach and Whalers Village ...
8.2/10 Very Good! (16 reviews)
"Worst hotel I have ever stayed in, check in was a nightmare, going back and forth with front desk, getting my room locked a couple times because my card wouldn’t get through some system failure, yet other guest had no problem, the first room I stayed in was dirty and fill with mosquitos, the shower ..."

Reviewed on May 19, 2026

Opens in a new windowRoyal Lahaina Bungalows & Spa
The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui

5 out of 5
One Bay Drive Lahaina HI
The price is CA $1,758 per night from Jun 10 to Jun 11
CA $1,758
CA $2,389 total
Jun 10 - Jun 11
includes taxes & fees
Book a stay at this luxury hotel in Kapalua. Enjoy free WiFi, a full-service spa, and 3 restaurants. Popular attractions Whalers Village and Kaanapali Beach ...
9.6/10 Exceptional! (211 reviews)
"Even though we booked under the montage name, the hotel met all standards even with new ownership. The property itself is one of the most magical places we have been. We are very excited to come back in the future with our family."

Reviewed on Apr 3, 2026

Opens in a new windowThe Resort at Kapalua Bay, Maui
Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM

5 out of 5
500 Bay Drive Kapalua HI
Book a stay at this luxury condo in Kapalua. Enjoy free parking, 2 outdoor pools, and a beach locale. Popular attractions Whalers Village and Napili Bay are ...
Opens in a new windowKapalua Bay Villas Resort by KBM
2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas

5 out of 5
938 S Kihei Rd Kihei HI
Book a stay at this luxury condo in Kihei. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Wailea Beach and Waipuilani Park are located ...
Opens in a new window2 2 Oceanview Modern Resort Vistas
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Five Star Hotels in Paia

Looking for your own little slice of heaven during your next trip? Check out all the best 5 star hotels in Paia to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the five star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Paia 5 star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5 star hotels in Paia before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

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