In Hawaiʻi, a swimming pool can be more than a private retreat. At the right property, it becomes a front-row seat to the islands’ most unforgettable scenery.
From beachfront estates where the ocean begins just beyond the lawn to elevated residences overlooking Maui’s neighboring islands, these Coldwell Banker Island Properties listings celebrate outdoor living on an extraordinary scale.
Here are eight remarkable Hawaiʻi homes where the pool is every bit as captivating as the view.
Resort-Inspired Escape on Keawakapu Beach
3060 South Kīhei Road, Kīhei, Maui
MLS 408751
Set directly along coveted Keawakapu Beach, this one-of-a-kind estate brings the feeling of a private resort home to South Maui. Its impressive poolscape features a slide, hot tub, waterfalls, and a dramatic rock grotto, all surrounded by tropical landscaping.
Beyond the pool, a generous oceanfront lawn leads toward the beach, creating a seamless progression from the residence to the Pacific. Multiple indoor and outdoor gathering spaces make this an exceptional setting for relaxed island living, hosting, and multigenerational stays.
Oceanfront Living on West Maui
4809 Lower Honoapiʻilani Road, Kahana, Maui
MLS 406991
This expansive West Maui estate combines more than 8,400 square feet of living space with a rare oceanfront setting. The property’s pool and outdoor areas offer a private place to enjoy the scenery, with the shoreline forming a remarkable natural backdrop.
Created for gathering on a grand scale, the residence includes seven bedrooms, nine baths, a detached ʻohana, and generous indoor-outdoor living areas. It is a true legacy offering where space, privacy, and proximity to the water come together.
A 70-Foot Pool Above the ʻAuʻau Channel
426 Wailau Place, Launiupoko, Maui
MLS 408714
From the uppermost heights of Launiupoko, this mountaintop retreat captures one of the most expansive ocean panoramas in the Hawaiian Islands. Its west-facing outlook stretches across the ʻAuʻau Channel, from Lānaʻi to Molokaʻi.
Massive retractable glass doors open the central living space to nearly 2,000 square feet of covered outdoor living. At the center is an extraordinary 70-foot-wide pool with a 12-foot-wide hot tub, accompanied by an outdoor kitchen and bar. With more than 25 acres surrounding the residence, the setting feels private, expansive, and completely connected to the landscape.
Contemporary Island Living in Puunoa Estates
325 Hokiokio Place, Kapalua, Maui
MLS 407837
Completed in 2024, this contemporary residence offers a refined interpretation of modern island living within Puunoa Estates. Set across more than five acres, the home pairs generous interiors with a private pool and expansive outdoor spaces.
The elevated setting opens the property to broad island views, while the single-level design creates an easy connection between the residence, pool terrace, and surrounding landscape. With nearly 5,000 square feet of living space, the home balances architectural presence with a relaxed sense of privacy.
Timeless Luxury in Kapalua’s Plantation Estates
223 Plantation Club Drive, Kapalua, Maui
MLS 408037
Within the prestigious Plantation Estates community, this single-level Kapalua residence offers more than two acres of private grounds and over 5,300 square feet of interior living.
The home’s pool and outdoor entertaining areas are surrounded by the beauty of West Maui, creating a private setting for slow mornings, sunlit afternoons, and evenings under the island sky. Furnished interiors, a sauna, and thoughtfully designed gathering spaces further enhance its resort-inspired appeal.
A Private Retreat in Kā‘anapali Golf Estates
1015 Anapuni Place, Lahaina, Maui
MLS 409785
Set within one of West Maui’s most desirable residential enclaves, this single-level home embraces the open-air lifestyle that defines luxury living in Hawaiʻi.
The private pool extends the living experience outdoors, while the property’s elevated setting creates a beautiful connection to the surrounding scenery. Four bedroom suites and approximately 4,000 square feet of living space provide an elegant balance of privacy, comfort, and room to entertain.
Grand-Scale Living at 104 Anapuni Loop
104 Anapuni Loop, Lahaina, Maui
MLS 408779
Nearly 6,000 square feet of interior living distinguishes this substantial West Maui residence. The home’s private pool and expansive grounds create a resort-like environment within a highly sought-after gated community.
Set on nearly an acre, the property offers ample space for entertaining while maintaining a sense of privacy. Its generous proportions, furnished interiors, and connection to the surrounding island views make it an impressive setting for year-round living or extended stays.
Where the Water Meets the View
The most memorable pools do more than complement a home. They frame the horizon, invite life outdoors, and create a deeper connection to the beauty of the islands.
Whether overlooking the Pacific, surrounded by tropical grounds, or set high above the coast, each of these exceptional properties offers its own interpretation of luxury poolside living in Hawaiʻi.
Explore more extraordinary homes through Coldwell Banker Island Properties’ Global Luxury collection, and discover a property where every day comes with a remarkable view.
Property information and availability were reviewed on July 21, 2026, and are subject to change. Listing information is deemed reliable but is not guaranteed.
