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Featured Paia 5 Star hotels

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 $1,084 per night from Feb 21 to Feb 22
CA $1,084
CA $1,376 total
Feb 21 - Feb 22
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)
Beautiful room with a great balcony and nice view (even at 45 degree angle), friendly staff at the pool and for room service, excellent restaurants and great food. A short walk to shops and other restaurants, and friendly concierge to book tours and excursions with if you want to do that. Wait lists ...

Reviewed on Feb 7, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
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 $966 per night from Mar 4 to Mar 5
CA $966
CA $1,235 total
Mar 4 - Mar 5
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! (1,001 reviews)
Clean room, great staff, pool was fun

Reviewed on Feb 13, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,228 per night from Feb 24 to Feb 25
CA $1,228
CA $1,538 total
Feb 24 - Feb 25
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! (999 reviews)
All around amazing experience. Gorgeous setting, great amenities, our trip went off without a hitch.

Reviewed on Jan 23, 2026

Opens in a new windowFairmont Kea Lani Maui
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
The price is CA $1,322 per night from Mar 7 to Mar 8
CA $1,322
CA $1,657 total
Mar 7 - Mar 8
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 ...
9/10 Wonderful! (1,001 reviews)
Yes it's secluded. Yes it is a large property that requires a lot of walking. The rooms are slightly dated. It's all made up by the attention and care from the staff at the Ritz. My wife and I were celebrating our honeymoon. We were treated with the utmost care from the kind folks there. The property ...

Reviewed on Jan 3, 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 $1,386 per night from Mar 1 to Mar 2
CA $1,386
CA $1,727 total
Mar 1 - Mar 2
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 ...
9.2/10 Wonderful! (1,000 reviews)
Rooms are beautiful

Reviewed on Jan 13, 2026

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay

Montage Kapalua Bay

5 out of 5
One Bay Drive Lahaina HI
The price is CA $1,909 per night from Mar 1 to Mar 2
CA $1,909
CA $2,471 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this luxury hotel in Kapalua. Enjoy free WiFi, a full-service spa, and a beach locale. Popular attractions Kaanapali Beach and Napili Bay are ...
9.6/10 Exceptional! (207 reviews)
Staff was great. Some maintenance issues, leaking water dispenser on fridge leading to pooling and warping of floor. Same on large lanai. Otherwise, great

Reviewed on Feb 14, 2026

Opens in a new windowMontage Kapalua Bay
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 $2,876 per night from Mar 1 to Mar 2
CA $2,876
CA $3,503 total
Mar 1 - Mar 2
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! (43 reviews)
Perfect for Families. Quite spacious and great for a relaxing Family vacation.

Reviewed on Jun 15, 2025

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 $552 per night from Mar 1 to Mar 2
CA $552
CA $728 total
Mar 1 - Mar 2
includes taxes & fees
Stay at this 5-star luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Kaanapali Beach and Whalers Village ...
9.4/10 Exceptional! (3 reviews)
Everything was amazing

Reviewed on Jan 5, 2026

Opens in a new windowRoyal Lahaina Bungalows & Spa
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

5 out of 5
4100 Wailea Alanui Dr-Building A Kihei HI
The price is CA $4,663 per night from Feb 25 to Feb 26
CA $4,663
CA $5,615 total
Feb 25 - Feb 26
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free breakfast, free valet parking, and 3 outdoor pools. Popular attractions Wailea Beach and Polo Beach are ...
9.6/10 Exceptional! (6 reviews)
It’s a decent hotel to stay for the family.

Reviewed on Aug 22, 2024

Opens in a new windowFairmont Kea Lani Maui Villa Experience
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 ...
9.8/10 Exceptional! (7 reviews)
The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful!

Reviewed on Dec 26, 2025

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.

Recent Paia hotel reviews by fellow wanderers