Hawaii · Family Vacations
Hawaii Family Vacations
Hand-priced family resort packages on Maui, Oahu, Kauai, and the Big Island — air, transfers, and resort credits handled by Travelin' with Theresa.
All packages
10 Hawaii family packages
Every package is custom-quoted with current pricing — tell us your dates and party size and you'll have a proposal in 24 hours.
MauiMaui
Grand Wailea, A Waldorf Astoria Resort
5 nights from $6,750 for 4 w/Air
- Lagoon Queen Queen Room
- Resort fees included with tax (value $65 per day)
- $250 Resort Credit
- Round-trip airport transfers
+ 2 more inclusions
Travel Window 08/23/26 – 12/15/26
Wailea's iconic family resort — nine pools, waterslides, river ride, and the best beachfront on south Maui.
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KauaiKauai
Grand Hyatt Kauai Resort & Spa
7 Days From $8,200 for 4 with Air
- Queen Queen Partial Ocean View room
- $250 Resort Credit
- Breakfast daily for 4
- Reduced resort fees
+ 3 more inclusions
Travel Window October 15, 2026 – December 15, 2026
Poipu's signature resort — saltwater lagoon, river pool, and one of Kauai's best beaches.
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MauiMaui
Hyatt Regency Maui Resort & Spa
7 days with Air from $6,950 for 4
- Queen Queen Partial Ocean View room
- $150 Resort Credit
- Full-size car
- Breakfast daily for 4
+ 3 more inclusions
Travel Window April 25 – December 15, 2026
Kaanapali Beach classic — penguin habitat, lagoon pool with waterslide, and oceanfront sunsets.
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OahuOahu
Hilton Hawaiian Village Waikiki Beach Resort
5 nights from $4,700 for 4 w/Air
- Rainbow Tower oceanfront room — two double beds
- 2 adults / 2 children
- Main cabin seating
- Round-trip airport transfers
+ 2 more inclusions
Travel Window August 8, 2026 – November 15, 2026
20 acres on Waikiki Beach — five pools, the only true Waikiki lagoon, and Friday fireworks.
View package- Oahu
Oahu
Disney's Aulani Resort & Spa
6 Days From $5,450 for Partial Oceanview
- Partial Ocean View Room
- Round Trip Airport Transfers
- 2 adults 2 children
- Air from LAX, SEA, OAK, SAN
Travel Window October 23, 2026 – December 20, 2026 (based on space availability)
Disney magic with Hawaiian heart — Ko Olina lagoons, kids' club, and character experiences.
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Oahu
Sheraton Waikiki
5 nights at $2,250 per person w/Air
- Oceanfront Room
- Breakfast Daily
- 1 complimentary Catamaran sail for two
- One $50 Resort Credit per room, per stay
+ 3 more inclusions
Infinity pool over Waikiki Beach, Diamond Head views, and an unbeatable beachfront location.
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MauiMaui
Sheraton Maui Resort & Spa
From $6,950 for 4 with Air
- Double Oceanview Room
- $100 DAily Resort Credit
- Full Size Car
- Depart from LAX, OAK, SFO, SJC, SEA, PDX, San Diego to Maui
Travel Window 4/15/26 - 06/30/26 Excludes Spring Break
Black Rock on Kaanapali Beach — snorkeling right off the sand and a relaxed family vibe.
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Big IslandBig Island
Fairmont Orchid
6 nights from $2,475 per person w/Air
- $50 daily resort fees included
- Partial Ocean View Room
- Full-size car
- Breakfast daily
+ 1 more inclusions
Travel Window Aug 25, 2026 – December 18, 2026
Kohala Coast luxury — protected snorkel cove, sea turtles on the beach, and resort-wide kids' programs.
View package- Multi-Island
Multi-Island
8-Day Kauai & Oahu Guided Tour Package
8 Days From $3,050 per person w/Air
- 4 Nights Sheraton Kauai Coconut Beach Resort
- Convertible Car in Kauai
- $150 Resort Credit in Kauai
- Snorkel and Kayak Excursion in Kauai inlcudes lunch
+ 5 more inclusions
All-inclusive 8 days across Kauai and Oahu — hotels, guided tours, and inter-island flights handled.
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MauiMaui
Fairmont Kea Lani, Maui
6 Days From $3,225 per person
- 5th night Free
- Jr Suite
- Breakfast Daily
- Airport Transfers fro OGG
+ 3 more inclusions
Travel Window 09/15/26 - 12/20/26 Price is based on space availability.
All-suite Wailea resort — extra space for families, three pools, and Polo Beach.
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