Vacation Package
Grand Wailea Family Vacation - Best Deal
- 5 nights · 09/23/26 – 12/15/26
- 4 guests with air
- Garden Queen Queen Room
- Breakfast daily for 2
- Resort fees included with tax (value $65 per day)
- $200 Resort Credit
- Round-trip airport transfers
- Main cabin seating
- Air from LAX, SAN, SEA, LAS, SFO, OAK
Price is based on space availability. Holiday travel is higher.
We have contracts nationwide — request a customized quote for your departure airport and travel dates.
- Napua Club Garden Queen Queen Room
- Club lounge breakfast, afternoon tea, and evening hors d’oeuvres
- Daily resort fees and personal concierge
- Ask about current Club package pricing with air
- Pool wristbands without the morning line: Wristbands are required daily for pool access and the waterslides. We brief families on the fastest towel-hut timing (aim for about 8:00 AM in peak season) and Napua Club shortcuts so you’re not stuck in a long queue while kids wait to swim.
- Save on casual lunches nearby: Skip resort lunch prices when you want something easy—Island Gourmet Markets at The Shops at Wailea is about a 5-minute walk from the lobby for poke bowls, snacks, and drinks at local prices.
- Preferred room placements: Our direct agent relationship with the resort means we submit custom room-location requests (higher Lagoon Tower floors, Wailea Wing beach access, quieter corners) so your family isn’t walking 15 minutes to the pools every morning.
Grand Wailea Maui Family Vacation Package: Insider Guide & Custom Deals
Planning a family trip to the Grand Wailea Maui (A Waldorf Astoria Resort) comes with big expectations—and a big investment. While the resort features 9 pools, families with young kids will want to set up base camp near the Lagoon pool early in the morning to stay close to the baby beach area without losing sight of the main slides.
As a certified luxury travel advisor, I don’t just book your room—I help you maximize resort credits, secure room upgrades where available, and plan your layout so your family isn’t walking 15 minutes to the pool every morning.
Why Book Your Grand Wailea Package With Travelin’ with Theresa?
When you book directly online, you get standard published rates. When you book through our agency privileges, you receive exclusive luxury advisor perks that cut down your out-of-pocket costs on-site:
- Daily Breakfast Credit: Up to $90/day credit toward breakfast for two guests per bedroom.
- Resort Credit: $200 resort credit per stay to apply toward Spa Grande or pool dining.
The Family Breakdown: Choosing the Right Room & Wing
The Grand Wailea is spread across 40 oceanfront acres. Choosing the wrong tower can mean long walks with tired toddlers or unexpected noise from lower-level walkways.
1. Terrace & Deluxe Garden Views (Best Budget Value)
The Reality: Located mainly in the Chapel or Lagoon wings. Our featured package category is the Garden Queen Queen Room—two queen beds, a private lanai, and garden views for a family of four.
Advisor Tip: If you choose a Terrace or Garden View room to save on the base price, request a room on a higher floor in the Lagoon Tower. You’ll stay closer to the main activity pools while avoiding foot-traffic noise on the ground floor.
2. Ocean View Rooms & Suites (Best Balance for Families)
The Reality: Offers views of the Pacific and Molokini Crater.
Advisor Tip: For families wanting quick access to the beach and pool without waiting for elevators, request lower-floor Ocean View rooms in the Wailea Wing.
3. The Napua Tower (The VIP Club Experience)
The Reality: A private hotel-within-a-hotel with a dedicated concierge lounge.
Is it worth it for families? Yes, if you have teenagers or a larger family. The inclusive continental breakfast, afternoon tea, and evening hors d’oeuvres/cocktails easily offset the cost of dining out three times a day in Wailea. See our Grand Wailea Club Room deals for current Napua Tower packages.
Essential Insider Tips for Families Staying at Grand Wailea
Navigating the Pools & Wristbands
While the resort features 9 pools, families with young kids will want to set up base camp near the Lagoon pool early in the morning to stay close to the baby beach area without losing sight of the main slides.
- Wristband Check-In: Wristbands are required daily for pool access and the waterslides. Head to the towel hut by 8:00 AM during peak holiday seasons to avoid morning queues—or ask us how Napua Club guests can streamline wristband pickup.
- Lounge Chair Etiquette: Unattended chairs holding towels are tagged by staff and cleared after 45 minutes. Grab your spots early near the Lagoon / baby beach area if you have little ones, or near the fishpipe pool for proximity to the kid slides.
Smart Dining Strategies
- Humuhumunukunukuapua’a: The floating lagoon restaurant is a must-do for sunset, but reservation slots fill up 30 days in advance. We pre-book dinner reservations for our clients before arrival.
- Off-Site Lunch & Snacks: The Island Gourmet Markets at The Shops at Wailea are a 5-minute walk from the resort lobby. It’s the best spot to grab fresh poke bowls, snacks, and drinks for the room at standard local prices.
Get a Custom Grand Wailea Package Quote
Every family vacation package is tailored to your exact dates, party size, and preferred room category. Let us handle the details, lock in your advisor perks, and ensure your resort credits are applied properly.
What’s included in your quote:
- Discounted resort room rate + Travel Leaders / advisor amenities
- Optional discounted roundtrip airfare & SUV rental car options
- Custom room location requests placed directly with resort management
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