Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana

    Mauna Kea Bluffs #5: La Ikena O Komohana

    Kamuela, HI

    Found on the sunny Kohala Coast of the Big Island of Hawaii, the Mauna Kea Bluffs #5 estate is conveniently located within an exclusive gated community. This magnificent estate home boasts 11,500 square feet of interior space. Every detail has been...

    Pool Hot Tub

    $10,240 to $12,620/night

  2. APARTMENT
    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    Kamuela, HI

    span style="font-size:16px;">This 8,000-square foot luxury estate with 2,750 square feet of outdoor living space is situated on a private, secure cul-de-sac in the Bluffs area of the Kohala Coast. The Beach House at the Bluffs features an...

    Pool Hot Tub

    $3,695 to $6,075/night

  3. VILLA
    Kahala Grand Splendor

    Kahala Grand Splendor

    Honolulu, HI

    Admiration starts at first glance with this contemporary vacation residence, completed in 2015 and boasting a huge pool, luxurious rooms with extravagant details, and central air conditioning. The tone of the home is set by a custom, solid mahogany...

    Pool Hot Tub

    $3,100 to $4,766/night

  4. HOUSE
    Hale Nui 2827

    Hale Nui 2827

    Lahaina, HI

    Thoughtfully designed with your comfort in mind, Hale Nui will exceed your expectations! After a long, arduous flight, each guest will feel embraced upon entering this exquisite, spacious home and everyone will immediately marvel at the panoramic...

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  5. VILLA
    Hale Waiulu #150470

    Hale Waiulu #150470

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views of...

    Pool Hot Tub

    $1,917 to $5,992/night

  6. HOUSE
    Hokulani

    Hokulani

    Honolulu, HI

    Hokulani, Hawaiian for “heavenly star,” is your next luxury vacation destination. New to the market, Hokulani is a relaxing executive estate in the heart of upscale Kahala. This meticulously planned estate furnished by the premier Orange...

    Pool Hot Tub Pets OK

    $1,821 to $4,082/night

  7. HOUSE
    CR 18 House of the Turtle at Champion Ridge, Mauna Lani

    CR 18 House of the Turtle at Champion Ridge, Mauna Lani

    Kamuela, HI

    Tranquility and luxury await in this single-level residence with spectacular Kohala Mountain views in the desirable gated Champion Ridge community. Situated in the heart of Mauna Lani, for convenient access to the finest beaches, golf, restaurants,...

    Pool Hot Tub

    $1,391 to $2,985/night

  8. HOUSE
    Mauna Kea Fairways North #9

    Mauna Kea Fairways North #9

    Kamuela, HI

    The vacation of a lifetime awaits at Mauna Kea Fairways North, a gated community within the premier resort area of Hawaii Island. Mauna Kea Fairways North #9 boasts three en suite bedrooms, air conditioning, a private pool and spa, and views of the...

    Pool Hot Tub

    $1,315 to $3,695/night

  9. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Relax and luxuriate in this spacious and bright four bedroom luxury property, newly renovated, redesigned and brand new to the rental market! Professional and cheerful Fine Design interior decor echoes tones of the nearby Pacific. Unwind on the...

    Pool Hot Tub

    $1,267 to $3,815/night

  10. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1,191 to $3,569/night

  11. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    This golf course-adjacent luxury home in a gated oceanfront community is the premier destination for a once-in-a-lifetime Hawaiian getaway. Offering over 3,000 square feet of island elegance with stunning views, a private pool and hot tub, and...

    Pool Hot Tub

    $1,182 to $3,373/night

  12. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Sweeping Ocean Views from Molokai to Lanai from this 8th floor Ocean Front condo. Floor to ceiling windows and doors bring the ocean views into the living area and the bedrooms. Ocean views can be enjoyed from the king bed in the master bedroom. The...

    Pool Hot Tub
    FREE CANCELLATION

    $1,089 to $1,445/night

  13. HOUSE
    Hawaii Happy Healthy House

    Hawaii Happy Healthy House

    Waimea, HI

    Hawaii Happy Healthy House is a five bedroom, five bathroom (plus powder room) located in the exclusive, gated Kohala Ranch community on the Big island of Hawaii. The Kohala Coast is one of the sunniest destinations in Hawaii with a unique blend of...

    Pool Hot Tub

    $1,089 to $1,513/night

  14. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1,056 to $3,132/night

  15. CONDOMINIUM
    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa 104

    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa...

    Kahuku, HI

    Ocean View & Beachfront Beach Level 4-Bedroom (2 Masters) Turtle Bay Villa 104 At Ocean Villa 104 you have dramatic ocean views from just about everywhere! My 4-bedroom villa is located on the beach level so you can walk right out your living room...

    Pool Hot Tub

    $1,037 to $3,517/night

  16. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high...

    Pool Hot Tub

    $970 to $2,856/night

  17. HOUSE
    Kainoa

    Kainoa

    Hanalei, HI

    KAINOA:TVNCU-1227: TA#148-488-1920-01 Walk to Hanalei Bay or to Hanalei shops and restaurants This beautifully appointed 4 bedroom, (two master suites) and 3 bath home with Hawaiian and Asian flair. Hardwood floors extend out to the deck in a...

    Hot Tub

    $787 to $992/night

  18. HOUSE
    Kolepa Hale

    Kolepa Hale

    koloa, HI

    This fabulous new home features a 32-foot swimming pool and jacuzzi on the fourth tee of the Kiahuna Plantation Golf Course offers over 2,500 square feet of island luxury, for an unforgettable Kauai getaway. Ideally situated in the exclusive Wainani...

    Pool Hot Tub

    $780 to $1,553/night

  19. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    This stunning Poipu home boasts over 3,300 square feet of elegant living space, along with sweeping views from the coastline up the sloping hills of Kalaheo. An open floor plan provides guests with the perfect setting for quality time together,...

    Pool Hot Tub

    $780 to $2,334/night

  20. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,540/night

  21. CONDOMINIUM
    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Kahuku, HI

    Direct Ocean & Beach View 2nd Level 3Bd (or 4bd w/adjoin studio) Villa 203This villa is located on the second floor in the most desirable location in the complex, just 20 yards from the sandy beach with direct ocean and beach views from just about...

    Pool Hot Tub

    $756 to $2,478/night

  22. CONDOMINIUM
    Ocean & Garden View Beach Level 3-Bed Villa 115

    Ocean & Garden View Beach Level 3-Bed Villa 115

    Kahuku, HI

    Beachfront Ocean & Garden View Beach Level by Pool & BBQs 3-Bed Villa 115 This beach level villa is just 20 yards from the sandy beach and 10 yards from the pool and BBQs! It has all new, top of the line, furniture including a sleeper sofa with a...

    Pool Hot Tub

    $703 to $2,348/night

  23. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Island living at its finest! Experience charming plantation style living in this gorgeous South Shore home. Enjoy all the Robert Trent Jones, Jr. community has to offer conveniently located along the Kiahuna Golf Course. Shopping, golf, and beach...

    Pool Hot Tub

    $702 to $1,910/night

  24. CONDOMINIUM
    Honua Kai Konea 301

    Honua Kai Konea 301

    Kaanapali, HI

    One of the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex. Konea 301 is one of only 5 Two Bedroom Ali'I Suites with Direct Ocean Views and private Outdoor Kitchens. At 1620 sq ft with a HUGE 415 sq ft lanai this gorgeous home has 180...

    Pool Hot Tub
    FREE CANCELLATION

    $700 to $2,287/night

  25. CONDOMINIUM
    Wailea Point #3401

    Wailea Point #3401

    Wailea, HI

    Wailea Point is a luxury condominium village located on the beach in Wailea. Every residence has a view of the ocean. It offers 3 heated swimming pools, a 25 meter lap pool, 2 hot tubs, pickle ball, paddle board and tennis courts, and a fitness...

    Pool Hot Tub
    FREE CANCELLATION
  26. CONDOMINIUM
    Direct Ocean View Beach Level 3Bed Villa 103

    Direct Ocean View Beach Level 3Bed Villa 103

    Kahuku, HI

    Direct Ocean View Beach Level 3Bed (or 4Bed w/Adjoin Studio) Villa 103 This villa is in the most desirable location in the complex. It has just 20 yards of lawn before the sandy beach and the pool and BBQs are just 50 yards to the right!  It has...

    Pool Hot Tub

    $677 to $2,609/night

  27. CONDOMINIUM
    Ocean & Pool View Beachfront 3rd Floor Penthouse Villa 309

    Ocean & Pool View Beachfront 3rd Floor Penthouse Vil...

    Kahuku, HI

    Ocean & Pool View Beachfront 3rd Floor (top) Penthouse Villa 309 This penthouse villa is located on the third level just steps from the sandy beach with beautiful ocean and pool views from the lanai, living room and master bedroom. It has a serene...

    Pool Hot Tub

    $651 to $2,217/night

  28. CONDOMINIUM
    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    Lahaina, HI

    Completely Remodeled and well-appointed one (1) bedroom, two (2) bath condo. Custom cabinetry, granite counter tops, built-in wine cooler and stainless steel appliances greet you as you walk in. Quality furnishings inspire luxury in this...

    Pool Hot Tub
    FREE CANCELLATION

    $634 to $824/night

  29. CONDOMINIUM
    Papakea K-402

    Papakea K-402

    Lahaina, HI

    The Ultimate Island getaway awaits you at our luxury 3 bedroom, 2-1/2 bath split level condo in West Maui!  Our beautifully furnished condo has spectacular views of the ocean making it the perfect place to whale watch (during season) and sip...

    Pool Hot Tub
    FREE CANCELLATION

    $603 to $860/night

  30. HOUSE
    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    Koloa, HI

    Experience a slice of heaven at Kiahuna Lani at Poipu. This beautiful 3 bed 3 bath home features privacy and comfort nestled within the exclusive Wainani community on Kauai's scenic and sunny South Shore. Enjoy the 1942 square foot spacious open...

    Pool Hot Tub

    $601 to $1,137/night