Luxury Vacation Rentals 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 59 vacation rentals – enter your dates for availability.
Kaanapali, HI, US
Wander Kaanapali NorthBeach
Next avail.
Dec 1 - Dec 4
38
Waimea, Hawaii
Wander Kamuela Coast
Next avail.
Dec 7 - Dec 9
612
Waimea, Hawaii
Wander Big Island Retreat
Next avail.
Dec 11 - Dec 14
512
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
Koloa, Hawaii
Wander Kauai Sanctuary
Next avail.
Dec 4 - Dec 7
412
Koloa, Hawaii
Wander Kauai Serenity
Next avail.
Dec 10 - Dec 13
38
Kailua-Kona, Hawaii
Wander Big Island Breeze
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Dec 3 - Dec 4
36
Kailua-Kona, Hawaii
Wander Big Island Cove
Next avail.
Jan 6 - Jan 11
414
Welcome to Hawaii
Experience the best of island living with Wander’s luxury vacation rentals in Hawaii. Our handpicked homes in Waimea, Koloa, Kailua-Kona, Kihei, and Princeville bring hotel-level consistency to the most coveted coastlines and upland settings.
Each residence pairs striking design with hotel-grade comforts like chef-ready kitchens, private pools or hot tubs, dedicated work zones, and ultra fast WiFi. Expect pristine housekeeping, plush linens, and 24/7 concierge support so your time on the islands feels effortless.
Whether you are planning a restorative escape or a productive workcation, a Wander makes it simple.
Destinations in Hawaii
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
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Dec 3 - Dec 4
512
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
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Dec 3 - Dec 5
514
Koloa, Hawaii
Wander Kauai Oasis
Next avail.
Dec 16 - Dec 19
622
Princeville, Hawaii
Wander Kauai Haven
48
Koloa, Hawaii
Wander Kauai Surf
Next avail.
Dec 3 - Dec 6
510
Kihei, HI, US
Wander Wailea Elua
Next avail.
Jan 18 - Jan 26
36
Kailua-Kona, Hawaii
Wander Big Island Escape
Next avail.
Dec 24 - Dec 25
38
Waimea, Hawaii
Wander Kamuela Glow
Next avail.
Dec 3 - Dec 5
48
Kailua-Kona, Hawaii
Wander Big Island Garden
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Dec 20 - Dec 21
48
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
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
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
Kaanapali, HI, US
Wander Kaanapali NorthBeach
Next avail.
Dec 1 - Dec 4
38
Waimea, Hawaii
Wander Kamuela Coast
Next avail.
Dec 7 - Dec 9
612
Waimea, Hawaii
Wander Big Island Retreat
Next avail.
Dec 11 - Dec 14
512
Hanalei, Hawaii
Wander Kauai Drift
Next avail.
Dec 12 - Dec 14
510
Koloa, Hawaii
Wander Kauai Sanctuary
Next avail.
Dec 4 - Dec 7
412
Koloa, Hawaii
Wander Kauai Serenity
Next avail.
Dec 10 - Dec 13
38
Kailua-Kona, Hawaii
Wander Big Island Breeze
Next avail.
Dec 3 - Dec 4
36
Kailua-Kona, Hawaii
Wander Big Island Cove
Next avail.
Jan 6 - Jan 11
414
Discover more of Hawaii
Hawaii rewards discerning travelers with distinct landscapes and microclimates across Kauai, Maui, and the Island of Hawaii. Princeville and Koloa reveal Kauai’s dramatic North and South Shores, from emerald ridgelines to calm coves perfect for unhurried days by the water.
On Maui, Kihei brings warm, dry weather and easy access to coastal adventures. On Hawai‘i Island, Kailua-Kona blends oceanfront buzz with coffee country, while Waimea offers cooler highland vistas and brilliant night skies.
With such variety in scenery, climate, and pace, this is why Wander's luxury vacation rentals in Hawaii are the perfect choice, whether you're traveling for work or leisure.