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Top 10 Oahu Luxury Vacation Rentals – Page 2

Honorable Mentions

breathtaking view from your own balcony at Kai Hale Suites Hawaii Luxury rental
Average $6,339/night

Kai Hale Suites

Waikiki, Hawaii

Enjoy your family vacation or romantic escape at Kai Hale Suites, centrally located on Waikiki Beach. Experience serene units with ocean views, a resort pool, private cabanas, and live entertainment. With a fitness center, day spa, and kids’ program, it’s the perfect home away from home…

2 Beds

2 Baths

2 Bedrooms

Kea Moana Vacation Rental on Oahu
Average $5,500/night

Kea Moana

Lanikai, Hawaii

This gorgeous 5 bedroom, 4.5 bathroom, the gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful…

7 Beds

5 Baths

5 Bedrooms

tropical and pool view at Kealoha Penthouse Hawaii property rental
Average $5,250/night

Kealoha Penthouse

Waikiki, Hawaii

Experience luxury at Kealoha Penthouse, a stunning 3-bedroom suite at the Hilton Hawaiian Village Grand Waikikian, offering panoramic ocean views, exclusive penthouse amenities, and full access to resort services. Enjoy top-tier accommodations at a fraction of the cost for an unforgettable stay…

3 Beds

3 Baths

3 Bedrooms

stunning exterior of Makani Nui Estate Hawaii property rental
Average $4,427/night

Makani Nui Estate

Honolulu, Hawaii

Discover luxury living at Makani Nui Estate, a stunning contemporary home nestled on a verdant hillside in Honolulu. This secluded sanctuary boasts over 6000 sq ft of elegant living space with walls of glass, exotic woods, Subzero kitchen appliances, and breathtaking ocean and city views…

4 Beds

5.5 Baths

4 Bedrooms

Moana kiʻi kiʻi Vacation Rental on Oahu
Average $4,000/night

Moana kiʻi kiʻi

Kahala, Hawaii

This oceanfront crown jewel – a modern diamond head home – offers a penthouse atmosphere for entertaining or quiet days watching ocean waves. This is a truly one-of-a-kind property with beach access. Located very near the Doris Duke “Shangri La,” this executive home…

5 Beds

5 Baths

4 Bedrooms

Kai Valhalla Vacation Rental on Oahu
Average $3,716/night

Kai Valhalla

Lanikai, Hawaii

With a private, gated entrance and a sophisticated and luxurious feel throughout, Kai Valhalla is the indulgence you need on your next Hawaiian vacation. This larger-than-life custom-built five-bedroom, four-and-a-half-bath home spread out over three stories is ideal…

6 Beds

5 Baths

5 Bedrooms

Koa Loft Oahu luxury Vacation Rental
Average $3,250/night

Koa Loft

Lanikai, Hawaii

Koa Loft – This four-bedroom, four-bathroom home is ideal for families. It features high vaulted ceilings, a large open living space, plenty of dining areas, a perfectly manicured yard, and access to a gorgeous white sand beach just yards away…

6 Beds

4 Baths

4 Bedrooms

Average $3,034/night

Honu Kai Villa

Kahuku, Hawaii

Discover luxury at Honu Kai Villa, a beach-level 3-bedroom retreat on Oahu’s North Shore within the Turtle Bay Resort. Enjoy direct access to a heated pool, jacuzzi, and the beach, along with top-notch amenities including a gourmet kitchen, spacious living areas, and reserved parking…

3 Beds

2 Baths

3 Bedrooms

Makai Retreat circular bar by the pool
Average $2,435/night

Makai Retreat

Waikiki, Hawaii

Experience the ultimate coastal escape at Makai Retreat, just steps from the beach. This family-friendly haven offers serene rooms with lanais, a stunning pool, and lush greenery. Enjoy the breathtaking views, all while being minutes from Waikiki Beach and world-class shopping…

8 Beds

4 Baths

4 Bedrooms

Hau' oli Hale backyard with panoramic ocean and sunset view
Average $1,491/night

Hau’ oli Hale

Waianae, Hawaii

Experience the ultimate family getaway at Hau’oli Hale, a breathtaking two-story home in the gated Cottages at Mauna Olu. Enjoy panoramic ocean and sunset views, luxurious amenities, and proximity to stunning beaches. This beautifully decorated retreat offers comfort, relaxation, and unforgettable memories…

6 Beds

2.5 Baths

4 Bedrooms

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