Hawaii Vacation Homes

Ocean Escape - 5BR Home

Rating: 5

• 5 Bed
• 4 Full Baths

From $3150.00 / night

This is a legally established property, please read below for more info... Hawaiiana home just steps from the world famous Kailua Beach. This Hawaiiana house second of two homes of the beachfront property. It is the perfect place to relax and enjoy paradise. The tropical large living room opens onto a spacious private lawn leading out directly via a secure gate beteen the two homes to a sandy walkway, steps to breathtaking Kailua beach. A rear private courtyard lanai with 15ft x 32ft

Oceanfront Bungalow Waimea Bay - 3BR Home

Rating: 4.7

• 3 Bed
• 2 Full Baths

From $3135.00 / night

Private, ocean front home on the North Shore of Oahu just steps from beautiful beaches - Waimea Bay and 3 Tables. (No roads to cross, so safe for kids...) Great snorkeling, swimming,...white sand beaches. Open-beam ceilings. High end finishes, sub-zero refrigerator. Spectacular views, lush landscaping, lanais with sliding doors from each of the 3 bedrooms. (3rd bedroom has a queen-size futon so it will sleep 6- room can also be opened up to be used as an extension off the living/dining/kitche

Ono Oasis - 3BR Home Ocean View + Private Pool

• 3 Bed
• 3 Full Baths

From $321.00 / night — Total price: $963.00

Ono Oasis is a striking retreat in Kailua Kona, HI, offering a private heated pool, lush tropical landscaping, and serene indooroutdoor living for an unforgettable Hawaiian getaway. Spanning 2,800 square feet, this elegantly crafted home accommodates up to six guests across three beautifully appointed bedroom suitesperfect for families or groups seeking tranquility, comfort, and island adventure. What Youll Love About Ono Oasis Private solar heated saltwater pool ideal for sunlit afternoons E

Piko Nani - 3BR Home Ocean View + Private Pool + Private Hot Tub

• 3 Bed
• 3 Full Baths

From $300.00 / night — Total price: $900.00

Perched on a picturesque hilltop with sweeping Pacific Ocean views, Piko Nani by Gather offers a serene luxury escape in Kailua Kona. Meaning Hilltop Beauty, Piko Nani lives up to its name with 2,740 square feet of elegant indoor living and expansive outdoor space, all surrounded by lush tropical landscaping and the propertys own fruit trees and coffee orchard. This private three-bedroom estate accommodates up to six guests and blends comfort, privacy, and island tranquility. What Youll Love Ab

Pineapple House - 3BR Home Ocean View

• 3 Bed
• 2 Full Baths

From $313.00 / night — Total price: $939.00

This elegant 3-bedroom, 2-bath home in the gated Keauhou Estates blends spacious island living with serene privacy. Set on the ground level with tropical gardens, city views, and a glimpse of the Pacific, it offers a refined retreat just minutes from downtown Kailua-Kona. What Youll Love About Pineapple House * Expansive great room with soaring ceilings & open-air design * Covered lanai with hot tub, BBQ & panoramic ocean views * Master suite with soaking tub, walk-in shower & wrap-around windo

Plantation Cottage at Poipu - 3BR Home Partial Ocean View + Private Hot Tub + Private Pool

• 3 Bed
• 3 Full Baths

From $750.00 / night — Total price: $2250.00

Experience island living at its finest at Plantation Cottage at Poipu, a beautifully crafted four-bedroom, three-and-a-half-bath retreat set along the first hole of the Kiahuna Golf Course in Koloa, Hawaii. Blending classic plantation-style architecture with contemporary comfort, this 3,000-square-foot home offers a private, tranquil setting just minutes from Poipu's beaches, dining, and outdoor adventures. What You'll Love About Plantation Cottage at Poipu Four thoughtfully designed sleeping

Pohaku Villa - 4BR Home Mountain View

• 4 Bed
• 3 Full Baths

From $650.00 / night — Total price: $1950.00

Welcome to Pohaku Villa, a spacious four bedroom, three bathroom North Shore Kauai vacation home set in the heart of Princeville. With a private pool, lush garden scenery, and air conditioned bedrooms, this residence delivers relaxed island living with the comfort of a thoughtfully designed retreat. Vaulted ceilings, warm flagstone floors, and wrap-around windows bring the outdoors in, while the covered lanai offers an effortless flow between indoor and outdoor spaces. What Youll Love About Poh

Portlock Paradise - 3+BR Home

Rating: 4.9

• 3 Bed
• 3 Full Baths

From $3300.00 / night

Set on the slopes of Koko Kai Crater, this spacious two story family-style home offers panoramic ocean views and breathtaking sunsets over Diamond Head. Large full kitchen, two living room areas and lots of lanais providing plenty of room for families and friends to relax. Decorated with a touch of island decor, the perfect house for indoor/outdoor living. The downstairs ocean view living room has a large TV complete with card table. Enjoy a swim in the private solar heated swimming pool or

Pualani Villa - 3BR Villa Garden View

• 3 Bed
• 2 Full Baths

From $375.00 / night — Total price: $1125.00

Escape to Pualani Villa by Gather, a stunning three-bedroom + den, 2.5-bathroom townhome in the heart of Princevilles prestigious resort community. Offering a beautifully designed living space, this two-story retreat combines modern luxury with island charm, creating the perfect getaway for families, groups, or long-term stays. Thoughtfully appointed with island-inspired dcor, spacious interiors, and high-end amenities, Pualani Villa is ideal for both relaxation and entertainment. What We Love

Rainbow Hale Estate - 3BR Home plus Den

Rating: 5

• 3 Bed
• 3 Full Baths

From $5025.00 / night

Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali a Family Retreat or Private Honeymoon Get -away. Surrounded by 5 acres of Maui tropical plantation, lies a spectacular estate like you've always dreamed of, with the lifestyle you've always dreamed of living. Secluded and in a private, gated community, it is convenient to all of West Maui's famous beaches, restaurants and activities. This property has 3 bedrooms, all with ensuite bathrooms, a bath, plus a 4th den/library, that is comp