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Hawaii Vacation Rentals with Sunset Views

Watching the Hawaiian sky come alive with color each evening is one of the most memorable parts of any island vacation. Our handpicked collection of rentals lets you savor the show in comfort-from your private lanai, pool deck, or ocean-facing window.

Choose from stylish condos, private villas, and spacious homes-all with westward-facing views that deliver breathtaking sunsets. Every listing on this page highlights a unique way to enjoy Hawaii’s golden hour.

Here are a few featured rentals:

• Honu Villa at Mauna Lani – A luxury 3-bedroom estate featuring a pool, outdoor lounge, and expansive views of the Kohala Coast at dusk.
• Golf Course View Condo in Waikoloa Village – Thoughtfully remodeled and set against open skies, this unit's lanai is ideal for wine-and-sunset moments.
• Elegant Princeville Retreat – With 3,100+ square feet and views over the Makai Golf Course, this 4-bedroom home offers some of Kauai’s best sunset vantage points.

Browse the listings below to find your perfect Hawaiian home base for evening skies and lasting memories.

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Luxury 3BR Home Near Heeia Bay in Kona

Welcome to Manukai Hale by Gather, a stunning 3-bedroom, 3-bathroom home situated on Manukai Street. This luxurious residence offers a spacious, open floorplan ideal for relaxing and entertaining, with contemporary updates and charming Boho decor throughout.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua Kona

from $687 

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Ko Olina Kai 1027A Luxury Ground-Floor Condo

Embark on an unforgettable Hawaii vacation at Ko Olina Kai 1027A by Gather, a stylish and comfortable two-bedroom, two-bathroom ground-floor condo nestled in the peaceful Ko Olina Kai community within the renowned Ko Olina Resort. This single-level home is perfect for up to four guests, offering a harmonious blend of modern comfort and island charm, ideal for extended stays and memorable vacations.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kapolei

from $461 

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On the Golf Course, Close to Pool, Beautifully Decorated

Located in the heart of Waikoloa Beach Resort near multiple golf courses.

You will love staying here for your island vacation!

This spacious 2 story, 2-bedroom, 2-bathroom condo boasts high 20+ ft ceilings in the living area to create a spacious feel, with plenty of windows that allow the natural light to come in.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Waikoloa

from $295 

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Private Kōloa Retreat | Pool + Golf Course Views | Near Poʻipū Beach

Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for a relaxing island retreat. With three full bathrooms including walk-in showers, a soaking tub in the master suite, and a private outdoor shower, guests can truly relax and unwind after a day of exploring Kaua‘i’s south shore.

• 3 bedroom
• 4 bathroom
• Sleeps 9

Hawaii> Koloa

from $1,406 

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Kapalua Golf Villa 16P7 with Fairway View and Spacious 2BR

Experience the perfect Hawaiian getaway in this charming 2-bedroom, 2-bath golf villa located on the first floor with stunning views of the Kapalua Bay Golf Course's 6th fairway. The villa offers a spacious 1344 sqft layout with a seamless blend of comfort and style.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Lahaina

from $758 

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Luxury Kapalua Villa with Ocean Views and Modern Amenities

Discover this beautifully appointed 1st-floor villa located in Kapalua, offering a blend of comfort and elegance. The property features a spacious layout with 1200-1500 sqft, perfect for up to four guests including children and infants. The villa is accessible via three stairs from the parking area, with plush carpeting in the living room, dining area, and bedroom, complemented by tile floors in the kitchen and bathrooms.

• 1 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Lahaina

from $804 

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Waikiki Mountain View Condo with Free Parking & Wi-Fi

Experience the perfect Hawaiian getaway in this charming Waikiki condo located just a block from the famous Waikiki Beach. The unit offers comfortable sleeping arrangements with two queen-sized beds in the bedroom and a sofa bed in the living room, accommodating families or groups comfortably.

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Honolulu

from $362 

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Luxury 3BR Townhome in Ko Olina Kai Resort

Welcome to your dream retreat in the heart of Ko Olina! This beautifully remodeled 3-bedroom, 3-bathroom townhome is nestled within the exclusive, gated community of Ko Olina Kai, offering a perfect blend of luxury, comfort, and island charm.

• 3 bedroom
• 3 bathroom
• Sleeps 7

Hawaii> Kapolei

from $393 

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Sunset/Ocean Views, Two pools, BBQ, Golf, Quiet

Welcome to the stunning and immaculate condo! We are happy to share our home with discerning guests looking for a get-away in Waikoloa Village. Our home features: Porcelain tile floors; Quartz kitchen counters; Tile and stone shower and bathroom; Samsung 65” QLED television; Chef’s kitchen with everything you’ll need to prepare a gourmet meal or quick snack; Leather recliners; Custom rosewood bedroom furniture.

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Waikoloa

from $202 

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Luxury Kapalua Ridge Villa with Ocean & Golf Views

Welcome to Kapalua Ridge Villa 1822, a beautifully remodeled one-bedroom, two-bath luxury townhouse nestled in the prestigious Kapalua Resort. This elegant property offers breathtaking partial ocean, mountain, and golf course views from every window, creating a perfect setting for a memorable Maui getaway.

• 1 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Lahaina

from $322 

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Quiet Condo, Gorgeous Views, Golf Course, 2 Pools

Upstairs Condo with Ocean View

Waikoloa Villa B202 promises guests exceptional sunsets and amazing golf course views and overlooking the 9th fairway of the Robert Trent Jones designed Waikoloa Village Golf Course. Guests get a golf discount with the amenity card located in the property.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Waikoloa

from $229 

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Golf Villas Gold Fairway View 2BR, Maui

Experience a relaxing getaway at Golf Villas Maui, located along the picturesque Kapalua Bay Course fairway. This spacious 2-bedroom, 2-bath villa offers between 1800 and 2200 sqft of comfort, accommodating up to 6 guests including children and infants.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Lahaina

from $791 

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Waikoloa Village Condo with Golf & Pool Access

Experience a comfortable stay at this inviting ground-floor condo in Waikoloa Village, Hawaii. Nestled in a secure, gated complex, this 785 sq ft unit offers two bedrooms and two bathrooms, ideal for families or groups of friends. The master bedroom features a plush king-size bed with an ensuite bathroom, while the second bedroom is equipped with twin beds that can be converted into a king-sized arrangement upon request, providing flexible sleeping options.

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Waikoloa

from $228 

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Luxury Ko Olina Kai 1081C Villa with Amenities

Discover the epitome of island elegance at Ko Olina Kai 1081C by Gather, a beautifully appointed three-bedroom, three-bathroom villa nestled within the charming Ko Olina Resort. This two-story vacation home comfortably accommodates up to six guests and features stunning real bamboo flooring throughout the main level, creating a warm and luxurious atmosphere as you step inside.

• 3 bedroom
• 3 bathroom
• Sleeps 7

Hawaii> Kapolei

from $653 

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View of Mauna Kea in Gated Community across from Golf Course

Quiet & Private 1 bed/1 day bed/1 bath kitchenette (attached to main house) w/ separate entrance & patio ~600 sqft in secluded & gated community at a cool 2400 ft elevation. Wake up to beautiful views of Mauna Kea. Located 30 min by car from Kona Airport, Waimea, Waikoloa, Kona town & 10 min from the "New Saddle Road entrance" that will get you to Hilo in 1 hour.

• 1 bedroom
• 1 bathroom
• Sleeps 3

Hawaii> Kailua-Kona

from $149 

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Luxury Estate at Hualalai Resort- Sweeping Ocean and Golf Course Views ** 2 Golf Carts**

A Sanctuary of Luxury – Lau‘eki Estates at Hualalai Resort

Discover refined Hawaiian living at its finest in this exceptional estate, nestled within the exclusive Lau‘eki Estates at the world-renowned Hualalai Resort.

A perfect harmony of tranquility, sophistication, and adventure awaits—set against a backdrop of lush tropical landscapes and panoramic views of the Pacific Ocean.

• 5 bedroom
• 7 bathroom
• Sleeps 10

Hawaii> Kailua Kona

from $7,744 

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Cozy 2BR Condo in Ko Olina Resort

Welcome to Hillside Villas 1498-3 by Gather, a cozy and well-maintained two-bedroom, two-and-a-half-bath condo nestled on the outskirts of the tranquil Ko Olina Resort in Hawaii. This charming townhome offers a perfect blend of modern comfort and tropical serenity, making it an ideal retreat for your vacation or extended stay.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kapolei

from $219 

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Luxury 3-Bedroom Ko Olina Resort Rental

Immerse yourself in the ultimate Hawaiian getaway at Ko Olina Kai 1105E by Gather, a beautifully furnished 3-bedroom, 2-bathroom upstairs unit nestled within the prestigious Ko Olina Resort. This luxurious retreat combines the comforts of a high-end home with the enchanting spirit of the islands, offering a perfect blend of relaxation and adventure.

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Kapolei

from $441 

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NEW!! Iconic Hawaiian Getaway at Mauna Lani. Beach, Bike, Golf, Books, Relax.

Parking Pass to Mauna Lani Beach Club Included.

Welcome to the Surf House in picturesque Kulalani, a gorgeous, upscale community within the world-class Mauna Lani Resort. This charming, light-filled two-bedroom townhouse is your perfect Hawaiian escape.

• 2 bedroom
• 2 bathroom
• Sleeps 5

Hawaii> Waimea

from $436 

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