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Wailea flight + hotel packages

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Price was $3,249, price is now $2,518 per person
per person
Dec 8 - Dec 14
Roundtrip flight included
Denver (DEN) to Kahului (OGG)
This aparthotel features 2 outdoor pools, a 24-hour fitness center, and a restaurant. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A bar/lounge, a 24-hour front desk, and a terrace are also provided.
Kaanapali Beach Club Resort by Diamond Resorts

Kaanapali Beach Club Resort by Diamond Resorts

3.5 out of 5
Save 100% on your flightPrice was $2,264, price is now $1,789 per person
per person
Oct 27 - Nov 3
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
This aparthotel features a restaurant, an outdoor pool, and a poolside bar. Families will appreciate the arcade/game room, barbecue grills, and supervised childcare. Enjoy the fitness center and perks like free valet parking and free WiFi.
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Price was $2,012, price is now $1,657 per person
per person
Oct 27 - Nov 3
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
This aparthotel features 2 outdoor pools, a spa tub, and a restaurant. Families will appreciate the arcade/game room, onsite laundry facilities, and supervised childcare. Enjoy the fitness center and perks like free WiFi.
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
Save 100% on your flightPrice was $3,545, price is now $2,980 per person
per person
Oct 27 - Nov 3
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
This smoke-free resort features a golf course, a full-service spa, and 5 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 6 outdoor pools and perks like free WiFi.
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
Save 100% on your flightPrice was $1,280, price is now $1,085 per person
per person
Nov 17 - Nov 22
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
This hotel features an outdoor pool and an outdoor tennis court. Enjoy the spa tub and perks like free self parking and free WiFi. A picnic area, dry cleaning, and barbecue grills are also on offer.

Top Wailea hotels deals

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is $749 per night
This luxury resort features a golf course, a full-service spa, and 4 restaurants. There's fun for all ages with a children's pool and a waterslide, and supervised childcare is an added bonus. Enjoy the 4 outdoor pools and perks like free WiFi.
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
Free Cancellation
Reserve now, pay when you stay
The price is $838 per night
A full-service spa, 6 restaurants, and 9 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi.
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 $1,550 per night
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a children's pool, and free childcare is an added bonus.
Hotel Wailea, Relais & Chateaux- Adults Only

Hotel Wailea, Relais & Chateaux- Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
The price is $874 per night
This luxury resort includes 2 restaurants, an outdoor pool, and a fitness center. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Unwind with a drink at the poolside bar and enjoy perks like a free beach shuttle.
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
The price is $929 per night
A full-service spa, 4 restaurants, and 5 outdoor pools are all featured at this luxury resort. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
Free Cancellation
Reserve now, pay when you stay
The price is $909 per night
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities.
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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.

Popular places to visit in Wailea

Image for Wailea Beach

Wailea Beach

4.5/5(1,614 reviews)

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

Wailea Beach
Image for Keawakapu Beach

Keawakapu Beach

4.5/5(85 reviews)

Enjoy the peace and quiet at one of Maui’s less crowded and wider beaches, where kids can wander around the rock pools, and divers can explore the artificial reef.

Keawakapu Beach
Image for Makena State Park Beach

Makena State Park Beach

4.5/5(438 reviews)

Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.

Makena State Park Beach

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