Wailea vacation packages from $639

Cheap Wailea package deals

These are the best prices for Aug 24 - 27.

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Kihei Akahi C-612 by Coldwell Banker Island Vacations - Wailea

Kihei Akahi C-612 by Coldwell Banker Island Vacations

9 Wonderful

Parking

Free Wi-Fi

Pool

Honolulu

Meals not included

3 nights + flight

$816

Grand Champions - Wailea - Living room

Grand Champions

Pool

Eugene

Meals not included

3 nights + flight

$976

Wailea Ekolu, #312 1 Bedroom Condo by RedAwning - Wailea - Balcony

Wailea Ekolu, #312 1 Bedroom Condo by RedAwning

Free Wi-Fi

Honolulu

Meals not included

3 nights + flight

$942

Wailea Grand Champion, #78 - Wailea

Wailea Grand Champion, #78

Free Wi-Fi

Honolulu

Meals not included

3 nights + flight

$1,169

Palms at Wailea Maui - Wailea - Building

Palms at Wailea Maui

7.9 Good

Parking

Free Wi-Fi

Pool

Spa

Honolulu

Meals not included

3 nights + flight

$639

Polo Beach Club - Coraltree Residence Collection - Wailea - Balcony

Polo Beach Club - Coraltree Residence Collection

8 Very good

Parking

Free Wi-Fi

Pool

Dallas/Fort Worth

Meals not included

3 nights + flight

$1,746

Wailea Beach Villas - Wailea - Balcony

Wailea Beach Villas

10 Wonderful

Parking

Free Wi-Fi

Honolulu

Meals not included

3 nights + flight

$1,828

Wailea Grand Champions - Maui Condo & Home - Wailea - Pool

Wailea Grand Champions - Maui Condo & Home

Free Wi-Fi

Pool

Honolulu

Meals not included

3 nights + flight

$817

Hotel Wailea - Wailea - Living room

Hotel Wailea

9.3 Wonderful

Free Wi-Fi

Pool

Spa

Honolulu

Meals not included

3 nights + flight

$1,277

Grand Wailea, A Waldorf Astoria Resort - Wailea - Pool

Grand Wailea, A Waldorf Astoria Resort

8.2 Very good

Free Wi-Fi

Pool

Spa

Lambert-St Louis

Meals not included

3 nights + flight

$1,429

Ho olei at Grand Wailea - Wailea - Restaurant

Ho olei at Grand Wailea

10 Wonderful

Parking

Pool

Spa

Eugene

Meals not included

3 nights + flight

$2,701

Kamaole Sands Two Bedrooms by Coldwell Banker Island Vacations - Wailea - Balcony

Kamaole Sands Two Bedrooms by Coldwell Banker Island Vacations

9 Wonderful

Free Wi-Fi

Honolulu

Meals not included

3 nights + flight

$980

Wailea Ekahi, #22d 1 Bedroom Condo by RedAwning - Wailea - Living room

Wailea Ekahi, #22d 1 Bedroom Condo by RedAwning

9 Wonderful

Pool

Honolulu

Meals not included

3 nights + flight

$1,602

Wailea Beach Resort - Marriott, Maui - Wailea - Restaurant

Wailea Beach Resort - Marriott, Maui

8.7 Very good

Free Wi-Fi

Pool

Spa

Eugene

Meals not included

3 nights + flight

$1,242

Andaz Maui at Wailea Resort - A Concept by Hyatt - Wailea - Pool

Andaz Maui at Wailea Resort - A Concept by Hyatt

8.4 Very good

Pool

Pet friendly

Spa

Eugene

Meals not included

3 nights + flight

$1,592

Fairmont Kea Lani, Maui - Wailea - Bedroom

Fairmont Kea Lani, Maui

9.3 Wonderful

Free Wi-Fi

Pool

Pet friendly

Spa

Eugene

Meals not included

3 nights + flight

$1,514

There are loads of types of vacations in Wailea and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $120; Family vacation $546; Romantic vacation $546; Luxury vacation $697.