Holidays in Wailea

Holidays in Wailea

2 travellers
Exact dates

KAYAK searches hundreds of travel sites at once for holiday package deals in Wailea

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Search
Best Deals

Cheap Wailea package deals

Most popular Wailea flight and hotel deals

Show all
Charming Beachside Garden Vistas - Wailea
Charming Beachside Garden Vistas - Wailea
Charming Beachside Garden Vistas
9.8 Wonderful
Parking
Free Wi-Fi
Pool
Air conditioning
San Francisco
Meals not included
3 nights + flight
£732
2BR Kihei Unit with 2 Baths, 3-Zone Split AC, In-Unit Laundry, Pool and Hot Tub! - Wailea
2BR Kihei Unit with 2 Baths, 3-Zone Split AC, In-Unit Laundry, Pool and Hot Tub! - Wailea
2BR Kihei Unit with 2 Baths, 3-Zone Split AC, In-Unit Laundry, Pool and Hot Tub!
9.8 Wonderful
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
£1,075
Luxurious & Spacious Ocean Vistas - Wailea - Pool
Luxurious & Spacious Ocean Vistas - Wailea - Pool
Luxurious & Spacious Ocean Vistas
9.7 Wonderful
Free Wi-Fi
Pool
Air conditioning
San Francisco
Meals not included
3 nights + flight
£1,018
Parking
Free Wi-Fi
Pool
Air conditioning
Seattle/Tacoma Intl
Meals not included
3 nights + flight
£887
Luxurious Wailea Ocean Vistas - Wailea - Balcony
Luxurious Wailea Ocean Vistas - Wailea - Balcony
Luxurious Wailea Ocean Vistas
10 Wonderful
Parking
Free Wi-Fi
Pool
Air conditioning
San Francisco
Meals not included
3 nights + flight
£993
Kamaole Sands by Maui Rental Group - Wailea - Pool
Kamaole Sands by Maui Rental Group - Wailea - Pool
Kamaole Sands by Maui Rental Group
Air conditioning
Spokane
Meals not included
3 nights + flight
£909
Parking
Free Wi-Fi
Pool
Air conditioning
San Francisco
Meals not included
3 nights + flight
£1,824
AC Hotels by Marriott Maui Wailea - Wailea - Patio
AC Hotels by Marriott Maui Wailea - Wailea - Patio
AC Hotels by Marriott Maui Wailea
8.2 Very Good
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Bozeman Gallatin Field
Breakfast
3 nights + flight
£798
Hotel Wailea Maui
9.3 Wonderful
Free Wi-Fi
Pool
Air conditioning
Omaha Eppley Airfield
Meals not included
3 nights + flight
£1,162
Free Wi-Fi
Pool
Air conditioning
Bozeman Gallatin Field
Meals not included
3 nights + flight
£1,069
Parking
Pool
Air conditioning
Bozeman Gallatin Field
Meals not included
3 nights + flight
£2,101
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Bozeman Gallatin Field
Breakfast
3 nights + flight
£846
Maui Banyan - Wailea
Maui Banyan - Wailea
Maui Banyan
7.6 Good
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
£579
Free Wi-Fi
Pool
Air conditioning
Bozeman Gallatin Field
Meals not included
3 nights + flight
£934
Pool
Pet-friendly
Air conditioning
Bozeman Gallatin Field
Meals not included
3 nights + flight
£1,156
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Bozeman Gallatin Field
Meals not included
3 nights + flight
£1,113

Last minute holiday packages to Wailea

Show all
Kihei Surfside #109 - Wailea
Kihei Surfside #109 - Wailea
Kihei Surfside #109
10 Wonderful
Parking
Free Wi-Fi
Pool
Air conditioning
Spokane
Meals not included
3 nights + flight
£1,061
The Villas at Fairmont Kea Lani - Wailea
The Villas at Fairmont Kea Lani - Wailea
The Villas at Fairmont Kea Lani
9.9 Wonderful
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Spokane
Meals not included
3 nights + flight
£4,450
Mana Kai #403 by Coldwell Banker Island Vacations - Wailea
Mana Kai #403 by Coldwell Banker Island Vacations - Wailea
Mana Kai #403 by Coldwell Banker Island Vacations
9 Wonderful
Parking
Free Wi-Fi
Pool
Air conditioning
Spokane
Meals not included
3 nights + flight
£1,760
Wailea Ekahi, #22d 1 Bedroom Condo by RedAwning - Wailea - Pool
Wailea Ekahi, #22d 1 Bedroom Condo by RedAwning - Wailea - Pool
Wailea Ekahi, #22d 1 Bedroom Condo by RedAwning
9 Wonderful
Spokane
Meals not included
3 nights + flight
£1,602

When to book a holiday in Wailea

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Wailea is on the southern, less exposed 'leeward' tip of Hawaii's Maui island. Surrounded by volcanic rocks and tree-green expanses stretching into the distance, Wailea holidays overlook the pristine deep-blue waters of the Pacific. Mixed with a relaxed local atmosphere away from the hustle and bustle, Wailea holidays offer visitors a true slice of island paradise.

Wailea

Planning Wailea Holidays

Wailea is lucky to enjoy less rain than other parts of Hawaii, and the best time to see its stunning beach-holiday beauty is during the balmy summer months. However, temperatures in winter are still mild, and this is a wonderful time to visit as whales migrate past the area and can be regularly spotted. Wailea is in the Hawaii-Aleutian timezone (UTC-10), and Wailea holidays are just a short car or taxi ride from the major airport at Kahului that receives many flights. Accommodation does not leave a lot of choice for budget travellers, however many of the prices for hotels and resorts are all-inclusive, so there are no extra hidden costs.

Wailea Highlights

Wailea holidays are simply not complete without visiting the beach; choose from one of the few dozen idyllic beaches all along the coast, but perhaps the best choice is the Makena Beach. Those looking for more active holidays try the Wailea Beach Walk, which combines a beach visit with a hike, or visit one of the various canoe and kayak rental facilities and enjoy a trip out onto the water. There is also much more to Wailea holidays than just its coastline, with several world-class golf courses to choose from for any sporting visitors, as well as a multitude of fabulous restaurants. Pick the perfect place to relax as the sunlight gently fades, whilst tasting the diverse cuisine on offer and replenish energy levels after a long day exploring.

Where to stay in Wailea

Our map will help you find the perfect place to stay for your holiday in Wailea by showing you the exact location of each hotel.