
Wailea Holidays from £1,597
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Your Wailea Holiday
Lock in a holiday package to Wailea and get set to experience its surfing, coastal beaches and views. However you'd like to spend your break in this picturesque neighbourhood, you'll find plenty of opportunities to mix relaxation and fun. Wondering what to see and do during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. No matter your travel plans or the size of your budget, booking your dream Wailea holiday has never been easier with Expedia.

Maui Beach Vacation Club
Reviewed on 4 Nov 2026




Signature Residences at Maui Banyan
Reviewed on 4 Nov 2026
Where to stay in Wailea

South Kihei
While visiting South Kihei, you might make a stop by sights like Kamaole Beach Park 2 and Kamaole Beach Park 3.
Top hotels in Wailea

Grand Wailea Maui, A Waldorf Astoria Resort

Four Seasons Resort Maui at Wailea

Fairmont Kea Lani Maui
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Reviewed on 30 Oct 2026
Frequently asked questions
Stay near popular Wailea attractions
Things to do

Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta

Sunset Dinner Cruise aboard Calypso: Prime Rib, Fish, Chicken or Pasta

Award-winning Dinner Cruise: Four Course Dining Experience
Explore a world of travel with Expedia
- Hotels near Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters
- Hotels near Kamaole Beach Park
- 3 Bedroom Suite w/Loft – Kamaole Sands 1401
- Aloha Aku Bamboo Suite – Discover Beachfront Serenity
- South Maui's Best Family Reunion Spot
- Aston Maui Hill Condo
- Beach Resorts & in Kihei
- This Blue Sky Escapes Studio Beachside condo/Walkout to Hot tub
- 🏝️😎🏄🏻Winter in Maui
- Castle at Maui Banyan
- Cozy Cute Condo Kihei Maui Vista Complex
- Cozy Maui 'Treehouse' with lovely views and amenities
- Experience Oceanfront Grandeur
- Halama Hale Private Home 4 Bedroom Home
- Hale Hui Kai 108 on Keawakapu Beach
- Island Charm
- Nani Kai Hale 307 on Sugar Beach
- Kamaole Beach Royale #312 3nd Flr
- Kamaole Sands 6
- Kamaole Sands 7
- Kihei Akahi Resort C313 Partial Oceanview
- Ocean view condo steps from Kamaole Beach and dining summer deals
- Garden Oasis w/ Partial Ocean Views
- Kihei Kai Nani #6
- Kihei Kai Nani #12
- Modern Oceanfront Escape
- Koa Resort 4F
- Leinaala Oceanfront #205 Oceanfront Views! A/C
- Super Summer Sale! Come Live da HI Life!
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- Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
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- Totally Renovated Maui paradise condo steps away from the beaches of South Kihei
- Modern Kihei Resort 2 Bedroom
- Nani Kai Hale #302 on Sugar Beach
- Budget Friendly
- ~Kamaole Sands~Owner Pd Resort Fees~UPDATED!~
- Updated Kauhale Makai unit 610 1 bedroom top floor
- Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
- Ocean View South Maui Condo with Lanai plus FREE parking
- Open Suite w/Bath Upgrades – Kamaole Sands 6306
- Spacious getaway w/Kitchen
- Rare
- Stunning Two Story Townhouse located in Ekahi Village!
- Sugar Beach Resort
- Sugar Beach Resort PH 14 Penthouse unit
- Sugar Beach Resort PH 29 Penthouse
- Tranquility Found w/OV lanai
- Specials
- Wailea Ekahi 10C
- Ocean View
- Wailea Ekolu #306 Panoramic Ocean Views on Wailea Golf Course
- Closest condo to Ulua Beach with perfect ocean/sunset views and complete privacy
- Waiohuli Beach Hale A
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.




















