7 Luxury Vacation Rentals with Incredible Pools You’ll Want To Swim In

There’s just something about a beautiful pool that takes a Hawaiian vacation to the next level. Morning laps with an ocean view, a cocktail-fueled afternoon in the sun, or a quiet midnight swim under the stars? These seven properties are all about poolside perfection for your next escape!

1. The Beach House | Kamuela, Big Island

Why You’ll Love It: This cliffside oasis features a private infinity pool that seems to spill right into the Pacific. Featuring indoor-outdoor living, tropical landscaping and panoramic views, it’s the definition of Hawaiian luxury.

Perfect for: Families, group getaways, and milestone celebrations.

2. Kai Moena | Kailua, Oahu

Why You’ll Love It: This expansive 7-bedroom estate blends modern elegance with barefoot luxury. The private pool and hot tub are perfect for post-beach relaxation, while the breezy lanai invite long, leisurely days in the sun.

Perfect for: Families, friend reunions, or group retreats in paradise.

3. Champion Ridge Home | Kamuela, Big Island

Why You’ll Love It: Located in the sought-after Mauna Lani Resort area, this elegant 4-bedroom estate blends island serenity with elevated design, featuring a private heated pool, spa, and lush tropical landscaping.

Perfect for: Families, couples traveling together, or anyone seeking space, style, and luxury on the Big Island.

4. Diamond Head Grandeur | Honolulu, Oahu

Why You’ll Love It: This 5-bedroom oceanview estate offers a private pool, spa, and unbeatable views of Diamond Head. Located on Honolulu’s prestigious Gold Coast, it’s a rare blend of luxury, privacy, and proximity to Waikiki.

Perfect for: Families, milestone getaways, and elevated island living.

5. Hale Kai‘opua | Koloa, Kauai

Why You’ll Love It: This 3-bedroom modern home blends contemporary elegance with the island’s natural beauty, while offering a private pool with ocean and golf views.

Perfect for: Families, couples, and small groups looking for a classic retreat.

6. Hale Ka Pua Ola at Kukui‘ula | Koloa, Kauai

Why You’ll Love It: This elegant 4-bedroom retreat in the private Kukui‘ula community features a resort-style pool, tropical gardens, and breezy indoor-outdoor living. A luxurious home base for exploring Kauai’s sunny South Shore.

Perfect for: Families, couples, and luxury travellers seeking privacy and resort perks.

7. Pili Pono | Honolulu, O‘ahu

Why You’ll Love It: This 5-bedroom oceanfront estate features a private pool, expansive lanais, and panoramic ocean views. With sleek interiors, soaring ceilings, and luxe indoor-outdoor living, it’s island luxury at its finest.

Perfect for: Upscale group getaways, family gatherings, or anyone seeking a front-row seat to paradise.