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Wailea Beach Vacation Packages

Wailea Beach Flight + Hotel Packages

Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this aparthotel in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Aston Maui Hill along with the latest prices and availability – book now.
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston Mahana at Kaanapali along with the latest prices and availability – book now.
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach condo in Kaanapali. Enjoy free parking, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby. Discover genuine guest reviews for Aston at The Whaler on Kaanapali Beach along with the latest prices and availability – book now.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach resort in Kihei. Enjoy 3 outdoor pools, 4 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Fairmont Kea Lani Maui, in Wailea neighborhood, along with the latest prices and availability – book now.
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
per person
May 20 - May 25
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Aston at the Maui Banyan along with the latest prices and availability – book now.
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a beach locale, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston Kaanapali Shores along with the latest prices and availability – book now.
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach aparthotel in Kaanapali. Enjoy free parking, 2 outdoor pools, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston Maui Kaanapali Villas along with the latest prices and availability – book now.
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
per person
May 20 - May 25
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach aparthotel in Kaanapali. Enjoy free parking, a garden, and a library. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston at Papakea Resort along with the latest prices and availability – book now.
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this beach resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and 4 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Andaz Maui at Wailea Resort - a concept by Hyatt, in Wailea neighborhood, along with the latest prices and availability – book now.
Kahana Villa

Kahana Villa

3 out of 5
per person
Jun 1 - Jun 6
Roundtrip flight included
Sacramento (SMF) to Kahului (OGG)
Stay at this 3-star condo in Napili-Honokowai. Enjoy free WiFi, free parking, and a sauna. Popular attractions Kaanapali Beach and Napili Bay are located nearby. Discover genuine guest reviews for Kahana Villa along with the latest prices and availability – book now.
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4 out of 5
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 4-star beach condo in Kaanapali. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for OUTRIGGER Honua Kai Resort & Spa along with the latest prices and availability – book now.
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
per person
May 20 - May 25
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this aparthotel in Napili-Honokowai. Enjoy free WiFi, a fitness center, and onsite parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby. Discover genuine guest reviews for Royal Kahana Maui by OUTRIGGER along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

3-4 Night Vacations in Wailea Beach

Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 11
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 11
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
Wailea
Save 100% on your flight
per person
Jun 7 - Jun 11
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 11
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Prices and availability subject to change. Additional terms may apply.

5-7 Night Vacations in Wailea Beach

Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
Wailea
Save 100% on your flight
per person
May 20 - May 26
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Prices and availability subject to change. Additional terms may apply.

Wailea Beach Last Minute Hotel Deals

Residence Inn by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea
3.5 out of 5
75 Wailea Ike, Kihei, HI
Stay at this 3.5-star business-friendly hotel in Kihei. Enjoy free breakfast, a free beach shuttle, and a 24-hour fitness center. Our guests praise the breakfast ...
Residence Inn by Marriott Maui Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
Grand Wailea Maui, A Waldorf Astoria Resort
5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
Stay at this beach resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and 5 restaurants. Our guests praise the helpful staff and the property condition in our ...
Grand Wailea Maui, A Waldorf Astoria Resort
Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui
4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
Stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. ...
Wailea Beach Resort - Marriott, Maui
Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea
5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
Stay at this beach resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the helpful staff and the property condition in our ...
Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui
Fairmont Kea Lani Maui
4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
Stay at this beach resort in Kihei. Enjoy 3 outdoor pools, 4 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
Fairmont Kea Lani Maui
Andaz Maui at Wailea Resort - a concept by Hyatt
Andaz Maui at Wailea Resort - a concept by Hyatt
4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
Stay at this beach resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and 4 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
Andaz Maui at Wailea Resort - a concept by Hyatt
Ho‘olei Villas at Grand Wailea
Ho‘olei Villas at Grand Wailea
5 out of 5
146 Ho'olei Circle, Kihei, HI
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Wailea Beach and Kamaole Beach Park are located ...
Ho‘olei Villas at Grand Wailea
Wailea Beach Villas
Wailea Beach Villas
4.5 out of 5
3800 Wailea Alanui Drive, Kihei, HI
Stay at this 4.5-star luxury aparthotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Kamaole Beach Park ...
Wailea Beach Villas
See all 5,549 properties in Wailea Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Book the perfect getaway to Wailea Beach

With Hotwire, booking your next trip to Wailea is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Wailea Beach while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Wailea Beach flight and hotel package for as low as $1,119.

Living it up in Wailea means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Wailea Beach, Wailea vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Wailea Beach for some of the best accommodations and flight deals.

FAQs about cheap Wailea Beach packages:

How to get cheap vacation deals to Wailea Beach?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $519.

How much are Wailea Beach packages?

Vacation packages to Wailea Beach vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $1,119.

How to find cheap car rentals near Wailea Beach?

Hotwire partners with some of the most reliable car rental companies in Wailea to bring you the best car rental deals in Wailea Beach for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Wailea Beach now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Wailea Beach right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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