![](https://forever.travel-assets.com/flex/flexmanager/images/2020/11/06/TVLY-MSJE-DTG-Hero-Image.jpg?impolicy=fcrop&w=900&h=225&q=mediumHigh)
Deals on vacations and trips to Wailea
Wailea flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
![OUTRIGGER Kaanapali Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/11600/11554/ac1d0f0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
This resort features a restaurant, an outdoor pool, and a bar/lounge. Dine at the beachfront restaurant and relax with beach cabanas. WiFi in public areas is free.
![Aston at The Whaler on Kaanapali Beach](https://images.trvl-media.com/lodging/1000000/70000/60400/60350/e8a75a75_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Aston at The Whaler on Kaanapali Beach
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
2 outdoor tennis courts, an outdoor pool, and A 24-hour gym are all featured at this smoke-free condo. There's a spa tub on site, and a 24-hour front desk and a terrace are also provided.
![Aston Mahana at Kaanapali](https://images.trvl-media.com/lodging/1000000/20000/12900/12900/dce7d964_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Aston Mahana at Kaanapali
Save 100% on your flight
per person
Sep 12 - Sep 17
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
An outdoor pool is featured at this aparthotel, along with a terrace and a garden. Enjoy the outdoor tennis court and perks like free self parking. A library, a picnic area, and luggage storage are also on offer.
![Aston Kaanapali Shores](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/7c59e90e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Aston Kaanapali Shores
Save 100% on your flight
per person
Sep 12 - Sep 17
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
This aparthotel's full-service spa, 2 outdoor pools, and 2 outdoor tennis courts are some of the highlights. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.
![Aston Maui Hill](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/ed8cad4e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Aston Maui Hill
Save 100% on your flight
per person
Sep 12 - Sep 17
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
This aparthotel features an outdoor pool and an outdoor tennis court. Enjoy the spa tub and perks like free self parking and free WiFi. A garden, dry cleaning, and concierge services are also on offer.
Top Wailea hotels deals
![Grand Wailea Maui, A Waldorf Astoria Resort](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/5b741036_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive, Kihei, HI
The price is $1,084 per night
$1,084
includes taxes & fees
$919 per night
Jul 28 - Jul 29
A full-service spa, 5 restaurants, and 9 outdoor pools are all featured at this resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. 2 poolside bars and 2 bars/lounges are featured at this resort, along with a gym.
Pool
Hot Tub
![Wailea Beach Resort - Marriott, Maui](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/6dd3c5e4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Wailea Beach Resort - Marriott, Maui
3700 Wailea Alanui Dr, Kihei, HI
The price is $762 per night
$762
includes taxes & fees
$646 per night
Aug 21 - Aug 22
A full-service spa, 4 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's pool and a waterslide, and supervised childcare is an added bonus. Enjoy the 2 spa tubs and perks like free WiFi.
![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/e1f9eeaf_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr, Kihei, HI
The price is $960 per night
$960
includes taxes & fees
$814 per night
Jul 31 - Aug 1
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this eco-certified 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.
Pool
Hot Tub
![Four Seasons Resort Maui at Wailea](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/d88f4bb3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive, Kihei, HI
The price is $1,292 per night
$1,292
includes taxes & fees
$1,095 per night
Aug 16 - Aug 17
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this 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 supervised childcare is an added bonus.
Pool
Hot Tub
![Andaz Maui at Wailea Resort - a concept by Hyatt](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/b559cbf2_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Andaz Maui at Wailea Resort - a concept by Hyatt
3550 Wailea Alanui Dr, Kihei, HI
The price is $900 per night
$900
includes taxes & fees
$763 per night
Aug 19 - Aug 20
A full-service spa, 4 restaurants, and 5 outdoor pools are all featured at this smoke-free 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.
Pool
Hot Tub
![Hotel Wailea, Relais & Chateaux - Adults Only](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/88cb1969_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street, Kihei, HI
The price is $1,108 per night
$1,108
includes taxes & fees
$939 per night
Jul 28 - Jul 29
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this luxury resort. Traveling for business? Take advantage of the business center, laundry service, and conference center. Enjoy the gym and perks like a free beach shuttle.
Pool
Spa
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
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.
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.
Maluaka Beach
4.5/5(101 reviews)
This is part of Maui’s so-called “Turtle Town,” a prime spot for sighting the inquisitive Hawaiian green turtles that are very common here.
Frequently asked questions
Photos of local treasures
Browse Wailea vacation photos for more inspiration
![Molokini featuring coral and marine life](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/37000/37443-Molokini.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)
Book a vacation to Wailea
Most popular
Hotels
Hotels with Free Parking in WaikikiHotels in HanamauluHotels in KahalaCheap Hotels in WaikikiHotels with Waterslides in WaikikiAll Inclusive Resorts & Hotels in CartagenaHotels near Ulua BeachBeach Resorts & Hotels in WaikikiHotels in WaikikiAll Inclusive Resorts & Hotels in WaikikiHotels with Hot Tubs in WaikikiExtended Stay Hotels ValdostaHotels in PoipuHotels in Summersville
Flights
Tucson to New York (TUS - LGA)Flights from Jonesboro MunicipalFlights to SchenectadyJetBlue Airways New York (JFK) to Rome (FCO) flightsDetroit to Dallas (DTW - DFW)JetBlue Airways Lima (LIM) to Fort Lauderdale (FLL) flightsJetBlue Airways Boston (BOS) to Key West (EYW) flightsPhilippine Airlines Manila (MNL) to Kalibo (KLO) flights
Cars