Luxury Vacation Rentals with a Private Pool 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 56 private pool 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
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Dec 7 - Dec 9
612
Waimea, Hawaii
Wander Big Island Retreat
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Dec 11 - Dec 14
512
Koloa, Hawaii
Wander Kauai Sanctuary
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Dec 4 - Dec 7
412
Koloa, Hawaii
Wander Kauai Serenity
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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
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Jan 6 - Jan 11
414
Kailua-Kona, Hawaii
Wander Big Island Garden
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Dec 20 - Dec 21
48
Welcome to private poolside luxury in Hawaii
Set your stay apart with Wander's luxury private pool vacation rentals in Hawaii. From Waimea, Koloa, and Princeville to Kailua-Kona and Kihei, our portfolio showcases contemporary design, sweeping island backdrops, and the consistency of a luxury hotel in a private home.
Every residence centers around a pristine private pool and generous outdoor lounging, paired with hotel-grade linens, fully equipped kitchens, ultra fast WiFi, and dedicated work zones. Professional cleaning and 24/7 concierge come standard, so you can arrive, unplug, and enjoy total privacy. If you want a beautiful space that looks exactly like the photos and performs like a five-star stay, this is it.
Kailua-Kona, Hawaii
Wander Kona Bay
Next avail.
Dec 6 - Dec 9
49
4.9
Kihei, Hawaii
Wander Maui Meadows
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Mar 1 - Mar 6
410
4.8
Kailua-Kona, Hawaii
Wander Kona Bay Shores
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Dec 3 - Dec 4
512
Waikoloa, Hawaii
Wander Waikōloa Beach
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Feb 7 - Feb 15
516
5
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
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Dec 16 - Dec 19
622
Princeville, Hawaii
Wander Kauai Haven
48
Koloa, Hawaii
Wander Kauai Surf
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Dec 3 - Dec 6
510
Kihei, HI, US
Wander Wailea Elua
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Jan 18 - Jan 26
36
Kailua-Kona, Hawaii
Wander Big Island Escape
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Dec 24 - Dec 25
38
Waimea, Hawaii
Wander Kamuela Glow
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Dec 3 - Dec 5
48
Kailua-Kona, Hawaii
Wander Big Island Garden
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Dec 20 - Dec 21
48
Koloa, Hawaii
Wander Kauai Pacific
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Dec 11 - Dec 17
412
Kailua-Kona, Hawaii
Wander Big Island Cove
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Jan 6 - Jan 11
414
Koloa, Hawaii
Wander Kauai Modern
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Jan 24 - Jan 27
410
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
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
Kailua-Kona, Hawaii
Wander Big Island Garden
Next avail.
Dec 20 - Dec 21
48
Discover more beyond the pool in Hawaii
Few destinations balance awe and ease like Hawaii. Lush valleys, lava fields, and luminous beaches sit within a short flight of each other, inviting a choose-your-own-pace escape across the islands.
Trade winds keep the climate comfortable, the ocean sets a daily rhythm, and golden hours feel almost cinematic. Between Kauai’s storied cliffs, the Big Island’s celestial night skies, and Maui’s warm shoreline, the scenery never repeats. This is why Wander's luxury private pool vacation rentals in Hawaii are the perfect choice, whether you're traveling for work or leisure.