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
12 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.
KauaiKauai
Grand Hyatt Kauai Resort & Spa
From $2,050per person for 47 days · October 15, 2026 – December 15, 20262 adults 2 children with air- Queen Queen Partial Ocean View room
- $250 Resort Credit
- Breakfast daily for 4
- Reduced resort fees
+ 3 more inclusions
Poipu's signature resort — saltwater lagoon, river pool, and one of Kauai's best beaches.
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MauiMaui
Fairmont Kea Lani, Maui
From $3,250per person for 26 days · 09/15/26 – 12/20/262 guests with air- 5th night free
- Jr Suite
- Breakfast daily
- Airport transfers from OGG
+ 2 more inclusions
All-suite Wailea resort — extra space for families, three pools, and Polo Beach.
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OahuOahu
Best Family Deal for Hilton Hawaiian Village
From $1,212.50p/person for 45 nights · 10/15/26 – 01/31/274 guests with air- Oceanview Special
- Main cabin seating, no charge, carry-on allowed
- 2 adults / 2 children
- Round-trip airport transfers
+ 2 more inclusions
5 Nights From $1,212.50 p/person for 4. Oceanview Special with air. Travel 10/15/26 – 01/31/27.
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MauiMaui
Grand Wailea, A Waldorf Astoria Resort
From $1,825p/person for 45 nights · Oct 20, 2026 – Jan 31, 20274 guests with air- Lagoon Room Queen Queen
- Resort fees waived
- Personal travel agent service
- $200 Resort Credit
+ 3 more inclusions
Wailea's iconic family resort — nine pools, waterslides, river ride, and the best beachfront on south Maui.
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MauiMaui
Sheraton Maui Resort & Spa
From $1,487.50p/person for 46 days · Oct 15, 2026 – Jan 31, 20274 guests with air- Oceanview Special
- Resort fees waived
- Full-size car
- Air from LAX, SAN, SFO, SEA, PDX, OAK, PHX
6 Days From $1,487.50 p/person for 4 at Black Rock — Oceanview Special, Resort fees waived, full-size car, and air including PDX. Travel Oct 15, 2026 – Jan 31, 2027.
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Multi-IslandMulti-Island
Maui & Oahu Vacation Package: 9 Days Sheraton Maui & OUTRIGGER Waikiki Beachcomber
From $1,812.50per person for 49 days · 10/01/26 – 01/31/272 adults 2 children with air- 5 nights Sheraton Maui Resort & Spa — Oceanview Room Two Doubles, 2 adults 2 children
- $100 daily dining credit (per room, per night)
- Resort fees waived
- Full Size Car — taxes included
+ 5 more inclusions
9 Days From $1,812.50 per person for 4 with Air — Oceanview Room Two Doubles at Sheraton Maui, Ocean View at OUTRIGGER Waikiki Beachcomber, full-size car taxes included, Kualoa Secret Island. Travel 10/01/26 – 01/31/27.
View package- Oahu
Oahu
Disney's Aulani Resort & Spa
From $5,450for 46 days · 10/23/26 – 12/20/264 guests with air- 6 days · Partial Ocean View Room
- 4 guests with air
- Round-trip airport transfers
- Disney kids club & character experiences included
+ 2 more inclusions
Disney magic with Hawaiian heart — Ko Olina lagoons, kids' club, and character experiences.
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MauiMaui
Hyatt Regency Maui Resort & Spa
From $1,850for 47 days · 09/15/26 – 12/20/262 adults 2 children with air- Queen Queen Partial Ocean View room
- $150 Resort Credit
- Full-size car
- Breakfast daily for 4
+ 3 more inclusions
Kaanapali Beach classic — penguin habitat, lagoon pool with waterslide, and oceanfront sunsets.
View package- Oahu
Oahu
Sheraton Waikiki
From $2,250per person5 nights · 06/10/26 - 10/31/262 guests with 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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Big IslandBig Island
Fairmont Orchid
From $2,475per person6 nights · Aug 25, 2026 – December 18, 20262 guests with air- $50 daily resort fees included
- Partial Ocean View Room
- Full-size car
- Breakfast daily
+ 1 more inclusions
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
From $3,050per person8 days2 guests with 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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KauaiKauai
Castle Kiahuna Plantation & Beach Bungalows
From $6,500for 46 nights · April 20, 2026 – August 31, 20264 guests with air- 1 Bedroom Oceanview Suite at Castle Kiahuna Plantation & Beach Bungalows
- Full-size rental car
- Cleaning fees ($298) included
- Air from LAX, SFO, SEA, SAN, SJC, OAK, PDX, PHX
Poipū beachfront condo — 1-bedroom oceanview suite, full-size car, and cleaning fees for families of four.
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