Holiday package deals in Wailea

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Tips for booking hotels in Wailea

Gain useful insights to help choose a hotel in Wailea. Data was last updated on Wed Mar 25 2026.
Cheapest month:May
Most expensive month:February
Average price in Wailea:£751/night
Cheapest price found:£122/night
Cheapest day:Monday
Most expensive day:Friday
£481 - £1,234
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£610 - £1,030
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Wailea vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Wed Mar 25 2026.
Four Seasons Resort Maui At Wailea
Four Seasons Resort Maui At Wailea

Four Seasons Resort Maui At Wailea

3900 Wailea Alanui Drive, Kīhei, Maui, HI, United States
0.0 mi from city centre
£3,774
Avg. per night
View Deal
Sheraton Maui Resort & Spa
Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

2605 Kaanapali Parkway, Kahului, Maui, HI, United States
0.0 mi from city centre
£2,238
Avg. per night
View Deal
Maui Coast Hotel
Maui Coast Hotel

Maui Coast Hotel

2259 South Kihei Road, Kīhei, Maui, HI, United States
0.0 mi from city centre
Free Wi-Fi
£1,714
Avg. per night
View Deal
Fairmont Kea Lani, Maui
Fairmont Kea Lani, Maui

Fairmont Kea Lani, Maui

4100 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.0 mi from city centre
£2,886
Avg. per night
View Deal
Grand Wailea, A Waldorf Astoria Resort
Grand Wailea, A Waldorf Astoria Resort

Grand Wailea, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.0 mi from city centre
£2,567
Avg. per night
View Deal
Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.0 mi from city centre
£2,071
Avg. per night
View Deal
Castle Kama'ole Sands
Castle Kama'ole Sands

Castle Kama'ole Sands

2695 South Kihei Road, Kīhei, Maui, HI, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£1,925
Avg. per night
View Deal
Andaz Maui at Wailea Resort - A Concept by Hyatt
Andaz Maui at Wailea Resort - A Concept by Hyatt

Andaz Maui at Wailea Resort - A Concept by Hyatt

3550 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.0 mi from city centre
£3,176
Avg. per night
View Deal
Courtyard by Marriott Maui Kahului Airport
Courtyard by Marriott Maui Kahului Airport

Courtyard by Marriott Maui Kahului Airport

532 Keolani Place, Kahului, Maui, HI, United States
0.0 mi from city centre
Free Wi-Fi
£1,820
Avg. per night
View Deal
See all

Where to stay in Wailea

Utilise the map to find the perfect place to stay for your trip to Wailea. There are 200 hotels to choose from in Wailea.

FAQ about Wailea holiday packages

Find answers to frequently asked questions Cheapflights users have about Wailea holiday deals.

  • How much are vacation packages to Wailea?

    Wailea holidays can be booked for as little as £1,714.

  • What is the cheapest time of year to travel to Wailea?

    Wailea holidays in September typically cost around £193.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Make sure to check back regularly as prices are subject to change.

  • What other destinations does Wailea have flight+hotel deals to?

    Remember to check back often to keep track of all the enticing offers for holiday packages to Wailea and more.

See more FAQs

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