Wailea vacation packages from $749

Cheap Wailea package deals

Discover the best prices by selecting your travel dates on KAYAK.

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Grand Champions 179 - Wailea - Living room

Grand Champions 179

San Francisco

Meals not included

3 nights + flight

$1,056

Palms at Wailea Maui - Wailea - Pool

Palms at Wailea Maui

8.3 Very good

Parking

Free Wi-Fi

Pool

Spa

Los Angeles

Meals not included

3 nights + flight

$802

Polo Beach Club - Coraltree Residence Collection - Wailea - Pool

Polo Beach Club - Coraltree Residence Collection

8 Very good

Free Wi-Fi

Kahului

Meals not included

3 nights + flight

$1,601

Kamaole Sands by VTrips - Wailea - Pool

Kamaole Sands by VTrips

Los Angeles

Meals not included

3 nights + flight

$972

Wailea Beach Villas - Wailea - Balcony

Wailea Beach Villas

9.6 Wonderful

Free Wi-Fi

Kahului

Meals not included

3 nights + flight

$1,974

AC Hotels by Marriott Maui Wailea - Wailea - Patio

AC Hotels by Marriott Maui Wailea

8.2 Very good

Free Wi-Fi

Pool

Pet friendly

New York John F Kennedy Intl

Meals not included

3 nights + flight

$944

Hale Kamaole 207 - Wailea

Hale Kamaole 207

Parking

Free Wi-Fi

Los Angeles

Meals not included

3 nights + flight

$974

Hotel Wailea - Wailea - Living room

Hotel Wailea

9.4 Wonderful

Free Wi-Fi

Pool

Spa

New York John F Kennedy Intl

Meals not included

3 nights + flight

$1,483

Grand Wailea, A Waldorf Astoria Resort - Wailea - Pool

Grand Wailea, A Waldorf Astoria Resort

8.2 Very good

Pool

Spa

San Francisco

Meals not included

3 nights + flight

$1,738

Maui Kamaole By To - Wailea - Living room

Maui Kamaole By To

10 Wonderful

Free Wi-Fi

Los Angeles

Meals not included

3 nights + flight

$957

Residence Inn by Marriott Maui Wailea - Wailea - Patio

Residence Inn by Marriott Maui Wailea

8.4 Very good

Free Wi-Fi

Pool

Pet friendly

New York John F Kennedy Intl

Breakfast

3 nights + flight

$891

Ho olei at Grand Wailea - Wailea - Bar

Ho olei at Grand Wailea

10 Wonderful

Parking

Pool

Spa

New York John F Kennedy Intl

Meals not included

3 nights + flight

$2,406

Mana Kai Maui - Wailea - Living room

Mana Kai Maui

6.3 Okay

Los Angeles

Meals not included

3 nights + flight

$937

Wailea Beach Resort - Marriott, Maui - Wailea - Restaurant

Wailea Beach Resort - Marriott, Maui

8.9 Very good

Free Wi-Fi

Pool

Spa

New York John F Kennedy Intl

Meals not included

3 nights + flight

$1,107

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

Andaz Maui at Wailea Resort - A Concept by Hyatt

8.6 Very good

Pool

Pet friendly

Spa

New York John F Kennedy Intl

Meals not included

3 nights + flight

$1,478

Fairmont Kea Lani, Maui - Wailea - Restaurant

Fairmont Kea Lani, Maui

9.2 Wonderful

Free Wi-Fi

Pool

Pet friendly

Spa

New York John F Kennedy Intl

Meals not included

3 nights + flight

$1,466

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 $1,271; Family vacation $1,313; Romantic vacation $1,124; Luxury vacation $1,106.