Wailea vacation packages from $715

Cheap Wailea package deals

These are the best prices for May 14 - 17.

Go to map

Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations - Wailea - Balcony

Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

Free Wi-Fi

San Francisco

Meals not included

3 nights + flight

$1,299

Kihei Surfside 412 1 Bedroom Condo - Wailea - Balcony

Kihei Surfside 412 1 Bedroom Condo

10 Wonderful

Free Wi-Fi

Kona Intl

Meals not included

3 nights + flight

$1,901

Palms at Wailea Maui - Wailea - Pool

Palms at Wailea Maui

7.9 Good

Parking

Free Wi-Fi

Pool

Spa

Kona Intl

Meals not included

3 nights + flight

$983

Polo Beach Club - Coraltree Residence Collection - Wailea - Balcony

Polo Beach Club - Coraltree Residence Collection

8.1 Very good

Parking

Free Wi-Fi

Pool

Kona Intl

Meals not included

3 nights + flight

$1,416

Grand Champions One Bedrooms by Coldwell Banker Island Vacations - Wailea - Balcony

Grand Champions One Bedrooms by Coldwell Banker Island Vacations

9.5 Wonderful

Free Wi-Fi

San Francisco

Meals not included

3 nights + flight

$1,259

Wailea Beach Villas - Wailea - Balcony

Wailea Beach Villas

9.6 Wonderful

Parking

Free Wi-Fi

Kona Intl

Meals not included

3 nights + flight

$1,898

AC Hotels by Marriott Maui Wailea - Wailea - Patio

AC Hotels by Marriott Maui Wailea

8.2 Very good

Free Wi-Fi

Pool

Pet friendly

Detroit Metropolitan Wayne County

Meals not included

3 nights + flight

$1,073

Hale Kamaole - Wailea

Hale Kamaole

7.9 Good

Free Wi-Fi

Pool

Kona Intl

Meals not included

3 nights + flight

$715

Hale Kamaole 207 - Wailea

Hale Kamaole 207

Parking

Free Wi-Fi

Kona Intl

Meals not included

3 nights + flight

$817

Hotel Wailea - Wailea - Living room

Hotel Wailea

9.3 Wonderful

Free Wi-Fi

Pool

Spa

San Francisco

Meals not included

3 nights + flight

$1,520

Grand Wailea, A Waldorf Astoria Resort - Wailea - Pool

Grand Wailea, A Waldorf Astoria Resort

8.2 Very good

Free Wi-Fi

Pool

Spa

San Francisco

Meals not included

3 nights + flight

$1,577

Mana Kai by Coldwell Banker Island Vacations - Wailea - Bedroom

Mana Kai by Coldwell Banker Island Vacations

5 Fair

Parking

Free Wi-Fi

Pool

Kona Intl

Meals not included

3 nights + flight

$2,068

Ho olei at Grand Wailea - Wailea - Restaurant

Ho olei at Grand Wailea

10 Wonderful

Parking

Pool

Spa

Detroit Metropolitan Wayne County

Meals not included

3 nights + flight

$2,568

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

Wailea Ekahi, #22d 1 Bedroom Condo by RedAwning

9 Wonderful

Pool

Kona Intl

Meals not included

3 nights + flight

$2,070

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

Andaz Maui at Wailea Resort - A Concept by Hyatt

8.5 Very good

Pool

Pet friendly

Spa

Phoenix Sky Harbor Intl

Meals not included

3 nights + flight

$1,763

Fairmont Kea Lani, Maui - Wailea - Restaurant

Fairmont Kea Lani, Maui

9.2 Wonderful

Free Wi-Fi

Pool

Pet friendly

Spa

Detroit Metropolitan Wayne County

Meals not included

3 nights + flight

$1,644

The Villas at Fairmont Kea Lani - Wailea

The Villas at Fairmont Kea Lani

10 Wonderful

Free Wi-Fi

Pool

Pet friendly

Spa

Phoenix Sky Harbor Intl

Meals not included

3 nights + flight

$7,406

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 $159; Family vacation $701; Romantic vacation $697; Luxury vacation $697.