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. HOUSE
    Bluffs 22- The Beach House at Mauna Kea Resort

    Bluffs 22- The Beach House at Mauna Kea Resort

    Kamuela, HI

    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 award-winning green design, original...

    Pool Hot Tub

    $3765 to $6145/night

  2. HOUSE
    Ali’i Honu Kai House

    Ali’i Honu Kai House

    Kailua-Kona, HI

    Perfectly located on the Kona “Gold Coast” of the Big Island between the charming village of Kailua~Kona and Keahou Bay, this home offers you your own personal paradise. From the moment you drive up to this dramatic gated, Ocean Front Estate you...

    Pool

    $3025 to $4840/night

  3. 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

    $2274 to $6318/night

  4. VILLA
    Hualalai Resort Palm Villa 140B

    Hualalai Resort Palm Villa 140B

    Kailua-Kona, HI

    This Hualalai Palm Villa is a spectacular three bedroom, three bath, two-story Hualalai condo on popular Waiulu Street at the world renowned Hualalai Resort. The Resort is home to the Four Seasons Hualalai, regarded by many as the #1 Resort in...

    Pool
    FREE CANCELLATION

    $1401 to $3736/night

  5. VILLA
    Hualalai Resort Fairway Villa 116D

    Hualalai Resort Fairway Villa 116D

    Kailua-Kona, HI

    Located on popular Waiulu Street just three minutes by golf cart to the Four Seasons Resort Hualalai, this large three bedroom single-level villa offers views of the 15th hole of the Hualalai Golf Course and ocean beyond. The villa is professionally...

    Pool
    FREE CANCELLATION

    $1284 to $3736/night

  6. HOUSE
    Pua Lani Home 69-1854

    Pua Lani Home 69-1854

    Waimea, HI

    A sophisticated touch of "old Hawaii" with easy ocean front living.  Large open spaces, Ocean views from two master suites, kitchen and living room with expansive covered lanai across the ocean side of the home.  Enter into two private landscaped...

    Pool

    $1210 to $2420/night

  7. HOUSE
    Aina Malia (4-Bedroom Home)

    Aina Malia (4-Bedroom Home)

    Waimea, HI

    This unique property is situated above beautiful Wailea Bay on the Kohala Coast of the Big Island of Hawaii, one of the few white sand beaches on the island of Hawaii. Beautiful tropical landscaping abounds with privacy and romance. Custom designed...

    $1204 to $2420/night

  8. VILLA
    Hualalai Palm Villa 140C

    Hualalai Palm Villa 140C

    Kailua-Kona, HI

    The spacious floor plan includes a downstairs master bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf...

    Pool
    FREE CANCELLATION

    $1168 to $3736/night

  9. VILLA
    Hualalai Resort- Palm Villa 130A

    Hualalai Resort- Palm Villa 130A

    Kailua-Kona, HI

    One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite opens...

    Pool
    FREE CANCELLATION

    $1168 to $3736/night

  10. VILLA
    Hualalai Resort- Waiulu 137D

    Hualalai Resort- Waiulu 137D

    Kailua-Kona, HI

    This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet of...

    Pool
    FREE CANCELLATION

    $1168 to $3736/night

  11. 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

    $1168 to $3647/night

  12. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    This oceanfront Kohala Coast home with breathtaking coastline views offers the ultimate setting for a once-in-a-lifetime escape to paradise. Decorated in a tranquil, elegant island style, it features two master suites, central air conditioning, and...

    $1147 to $3299/night

  13. VILLA
    Hualalai Resort Ke Alaula Villa 210A

    Hualalai Resort Ke Alaula Villa 210A

    Kailua-Kona, HI

    Spectacular three bedroom three bath villa centrally located within the Hualalai Resort. Two story townhome style in the exclusive Ke Alaula neighborhood, just a 3-4 minute cart ride to the Four Seasons Hotel. Fully receding pocket glass, screen and...

    FREE CANCELLATION

    $1109 to $3736/night

  14. VILLA
    Hualalai Resort Hillside 4102

    Hualalai Resort Hillside 4102

    Kailua-Kona, HI

    Location-Location-Location! This spectacular 2 bedroom, 2 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the soothing sounds of gentle waves on the shoreline from this ground...

    Pool
    FREE CANCELLATION

    $1109 to $3736/night

  15. 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

    $1089 to $1513/night

  16. 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

    $1089 to $1445/night

  17. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Ocean Front like you’ve never seen before! Located on the end of the building, this condo sits right on the world famous, Ka’anapali Beach. Enjoy spectacular ocean views from each room, whether you are relaxing on the couch, lying in bed or...

    Pool
    FREE CANCELLATION

    $1089 to $1445/night

  18. VILLA
    Hualalai Resort Fairway Villa 104D

    Hualalai Resort Fairway Villa 104D

    Kailua-Kona, HI

    Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are...

    Pool
    FREE CANCELLATION

    $934 to $2335/night

  19. CONDOMINIUM
    Whaler at Kaanapali Beach 723

    Whaler at Kaanapali Beach 723

    Lahaina, HI

    Mauka to Makai, translates to: the Mountain to the Ocean, which is the expansive views you have from the wrap around lanai of this two (2) bedroom condo. This open and spacious condo offer sweeping views of Mauna Kahalawai (West Maui Mountains), the...

    Pool
    FREE CANCELLATION

    $895 to $1231/night

  20. CONDOMINIUM
    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    Lahaina, HI

    Expansive floor plan creates a very spacious two (2) bedroom, two (2) bath condo. This well appointed condo has been completely remodeled with top of the line finishes and furnishings. The lanai wraps around from the mountain side to the center...

    Pool
    FREE CANCELLATION

    $895 to $1231/night

  21. 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

    $881 to $1110/night

  22. APARTMENT
    Diamond Head Beach Hotel R2

    Diamond Head Beach Hotel R2

    Honolulu, HI

    One of a Kind 3 Bedroom 2 Bathroom Penthouse on Oahu's Gold Coast Hovering over the ocean, and surrounded by windows, this flat has direct ocean views out of every window. Recently renovated, this full 3 bedroom apartment has a spacious open...

    FREE CANCELLATION

    $878 to $1001/night

  23. 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

    $860 to $2609/night

  24. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kalilua Kona, HI

    What is better than a Hawaiian sunset over the ocean? A sunset over the ocean that you can take in from the privacy of your tropical home-away-from-home! With nearly 5,000 square feet of indoor/outdoor living space, including a lanai with a pool...

    Pool

    $853 to $1769/night

  25. 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

    $808 to $2478/night

  26. 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 $1051/night

  27. 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

    $756 to $2348/night

  28. HOUSE
    Honu Ohana House 69-1757

    Honu Ohana House 69-1757

    Waimea, HI

    This is a big, fun beach house with several areas to enjoy as a whole group or to tuck away from the rest of the group’s festivities for some private time. Perfect for multi-generational families and/or extended family with friends. The home is...

    Pool

    $756 to $1585/night

  29. CONDOMINIUM
    Kaanapali Alii 456

    Kaanapali Alii 456

    Lahaina, HI

    Our Luxury Ocean View condo is PRIVATELY MANAGED. Our condo is not in the Rental Program, so rest assure that our condo photos that you see here, is the one that you will rent from us. The condo unit is located in building 4 on the 5th floor end...

    Pool
    FREE CANCELLATION

    $749 to $1500/night

  30. 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

    $703 to $2217/night