Luxury Vacation Rentals for Families in Hawaii
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 58 family vacation rentals – enter your dates for availability.
Kihei, HI, US
Wander Kihei Shores
24
Kailua-Kona, Hawaii
Wander Big Island Breeze
Next avail.
Dec 3 - Dec 4
36
Kihei, HI, US
Wander Wailea Elua
Next avail.
Jan 18 - Jan 26
36
Koloa, Hawaii
Wander Kauai Golf
Next avail.
Dec 8 - Dec 13
36
Kihei, HI, US
Wander Wailea Oceanview
Next avail.
Mar 8 - Mar 16
26
Kihei, HI, US
Wander Wailea Palms
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Dec 14 - Dec 16
26
Kihei, HI, US
Wander Kihei Dunes
Next avail.
Feb 21 - Mar 1
26
Kailua-Kona, Hawaii
Wander Big Island Bay
Next avail.
Feb 25 - Mar 2
36
Welcome to family adventures in Hawaii
Our luxury family vacation rentals in Hawaii pair the polish of a five-star stay with the ease of a private home. Multi-bedroom layouts, airy great rooms, and indoor-outdoor living give everyone space to gather and space to unwind.
Settle into ocean-view villas in Princeville and Koloa, contemporary coastal homes in Kihei, or sunlit retreats in Kailua-Kona and Waimea. Expect hotel-grade amenities like ultra fast WiFi, gyms and pools, pristine cleaning, and 24/7 concierge, plus thoughtful work areas so parents can stay connected when needed.
Kailua-Kona, Hawaii
Wander Kona Bay
Next avail.
Dec 6 - Dec 9
49
4.9
Kihei, Hawaii
Wander Maui Meadows
Next avail.
Mar 1 - Mar 6
410
4.8
Kailua-Kona, Hawaii
Wander Kona Bay Shores
Next avail.
Dec 3 - Dec 4
512
Waikoloa, Hawaii
Wander Waikōloa Beach
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Feb 7 - Feb 15
516
5
Hanalei, Hawaii
Wander Kauai Drift
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Dec 12 - Dec 14
510
Kailua-Kona, Hawaii
Wander Big Island Escape
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Dec 24 - Dec 25
38
Princeville, Hawaii
Wander Kauai Oceanfront
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Dec 5 - Dec 7
48
Koloa, Hawaii
Wander Kauai Shores
Next avail.
Dec 3 - Dec 5
514
Koloa, Hawaii
Wander Kauai Surf
Next avail.
Dec 3 - Dec 6
510
Waimea, Hawaii
Wander Kamuela Glow
Next avail.
Dec 3 - Dec 5
48
Koloa, Hawaii
Wander Kauai Pacific
Next avail.
Dec 11 - Dec 17
412
Kailua-Kona, Hawaii
Wander Big Island Cove
Next avail.
Jan 6 - Jan 11
414
Koloa, Hawaii
Wander Kauai Modern
Next avail.
Jan 24 - Jan 27
410
Waimea, Hawaii
Wander Big Island Retreat
Next avail.
Dec 11 - Dec 14
512
Waimea, Hawaii
Wander Big Island Estate
Next avail.
Dec 8 - Dec 10
410
Waimea, Hawaii
Wander Big Island Falls
Next avail.
Dec 3 - Dec 4
510
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Hawaii
Kihei, HI, US
Wander Kihei Shores
24
Kailua-Kona, Hawaii
Wander Big Island Breeze
Next avail.
Dec 3 - Dec 4
36
Kihei, HI, US
Wander Wailea Elua
Next avail.
Jan 18 - Jan 26
36
Koloa, Hawaii
Wander Kauai Golf
Next avail.
Dec 8 - Dec 13
36
Kihei, HI, US
Wander Wailea Oceanview
Next avail.
Mar 8 - Mar 16
26
Kihei, HI, US
Wander Wailea Palms
Next avail.
Dec 14 - Dec 16
26
Kihei, HI, US
Wander Kihei Dunes
Next avail.
Feb 21 - Mar 1
26
Kailua-Kona, Hawaii
Wander Big Island Bay
Next avail.
Feb 25 - Mar 2
36
Discover more family fun in Hawaii
From Kauai’s emerald cliffs to Maui’s sunlit shores and the Island of Hawaii’s lava-carved coastlines, the state offers a rare blend of beauty and variety for all ages. Koloa’s south shore brings calm waters, Princeville reveals dramatic ridgelines and crescent bays, Kihei delivers golden beaches and easygoing days, Kailua-Kona serves up radiant sunsets, and Waimea opens to cool upcountry ranch lands.
Year-round warmth, seasonal whale sightings, stargazing skies, and a rich Native Hawaiian heritage create a setting families remember long after the trip. With convenient mainland access and smooth interisland travel, planning is simple. This is why Wander’s luxury family vacation rentals in Hawaii are the perfect choice, whether you’re traveling for work or leisure.