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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters

Search results

  1. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Kauhale Pilialoha Indulge yourself in the ultimate in island style luxury, at the Big Island of Hawaii’s most exclusive retreat – Kauhale Pilialoha.  Experience breathtaking sunsets and enjoy the natural beauty of Hawaii from the ultimate...

    Pool Hot Tub

    $18,953 to $29,061/night

  2. 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

  3. 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

  4. 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

    $2,022 to $6,318/night

  5. 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 $3,796/night

  6. HOUSE
    Hale Keanu- Waimea Home

    Hale Keanu- Waimea Home

    Waimea, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort. At this single level brand-new home, you will find a...

    Pool Hot Tub

    $1,264 to $3,032/night

  7. 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 $3,552/night

  8. 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 $3,356/night

  9. CONDOMINIUM
    Honua Kai Konea 1019

    Honua Kai Konea 1019

    Kaanapali, HI

    Unbelievable KONEA 10th FLOOR CORNER PENTHOUSE -PANORAMIC VIEWS above the resort not looking into the courtyard. The 180 degree view of the blue pacific ocean, the islands of lanai and molokai, Black Rock and Maui Mountains! One of only four homes...

    Pool Hot Tub
    FREE CANCELLATION

    $1,140 to $3,452/night

  10. 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

  11. 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

  12. 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 $3,117/night

  13. 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 $2,842/night

  14. CONDOMINIUM
    Hale Lelea Ko Olina Beach Villa (B310)

    Hale Lelea Ko Olina Beach Villa (B310)

    Kapolei, HI

    This vacation home has been registered as a Transient Accommodation with the State of Hawaii – HAWAII TAX ID TA-083-717-4272-01 #groundfloor #view #oceanview #whitewater #group  #wedding #KoOlina #resort #luxury #villa #Kapolei #Oahu #Hawaii...

    Pool Hot Tub

    $856 to $2,016/night

  15. CONDOMINIUM
    Villa 316

    Villa 316

    Kahuku, HI

    This penthouse villa is located in the most desirable location in the complex, on the third level just steps from the sandy beach with panoramic ocean views and a private serene lanai. This villa is only about 20 yards from the ocean! Photographs...

    Pool Hot Tub

    $808 to $2,609/night

  16. 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

  17. CONDOMINIUM
    Honua Kai Hokulani 709

    Honua Kai Hokulani 709

    Kaanapali, HI

    Never before offered for rental, Honua kai Hokulani 709 is clearly the best 2 bedroom condo available in the Hokulani Building. Top of the highly desirable "09" stack, it just doesn't get any better than this. The best Ocean views from INSIDE the...

    Pool Hot Tub
    FREE CANCELLATION

    $696 to $2,092/night

  18. 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
  19. CONDOMINIUM
    B-110: Hale Papakea Ko Olina Beach Villa

    B-110: Hale Papakea Ko Olina Beach Villa

    Kapolei, HI

    One of only two ground floor beachfront 2 bedroom 2 bathroom condos that are closer to the beach than any other Ko'Olina Resort residence. Experience the ultimate oceanfront experience with family and friends. We manage both beachfront units, which...

    Pool Hot Tub

    $682 to $2,016/night

  20. CONDOMINIUM
    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    Kapolei, HI

    The Hale Nani Ikena Kai beach villa at Ko Olina offers exactly what its name suggests; a home with a “Beautiful Ocean View”. Spectacular direct whitewater ocean and beach views will be what greets you at this upscale, luxurious ground floor...

    Pool Hot Tub

    $682 to $2,016/night

  21. CONDOMINIUM
    Ko Olina Beach Villa (O121)

    Ko Olina Beach Villa (O121)

    Kapolei, HI

    Celebrities want privacy and quick exit routes, but so does everyone else! You deserve this one-of-a-kind Ko Olina Beach Villa, unlike any other located within the resort. It boasts over 1600 sq.ft of living space, 3 ground floor private lanais, no...

    Pool Hot Tub

    $682 to $1,668/night

  22. CONDOMINIUM
    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Kahuku, HI

    This villa is located on the second level with Spectacular Ocean and pool views from the lanai, the living room, the dining room, and the master bedroom! This villa is just 35 yards from the sandy beach and 10 yards to the Pool and BBQs. It has...

    Pool Hot Tub

    $677 to $2,217/night

  23. 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

  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

    $633 to $2,287/night

  25. CONDOMINIUM
    Honua Kai Konea 501

    Honua Kai Konea 501

    Kaanapali, HI

    Konea 501 is the top unit 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 degree views and SUNSETS ALL YEAR LONG. Watch the Whales in...

    Pool Hot Tub
    FREE CANCELLATION

    $620 to $2,167/night

  26. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Wailea Elua is the premier ocean front property in Wailea. A gated property situated right on picturesque Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean. In addition, the...

    Pool Hot Tub
    FREE CANCELLATION

    $609 to $1,073/night

  27. CONDOMINIUM
    Honua Kai Hokulani 509

    Honua Kai Hokulani 509

    Kaanapali, HI

    Hokulani #509 is located in one of the most desirable stacks on the entire property. Forward facing interior corner view location for catching the whales or just watching the SUNSET. This fabulous 2 bedroom/2 bath upgraded condo is in the Hokulani...

    Pool Hot Tub
    FREE CANCELLATION

    $595 to $1,871/night

  28. CONDOMINIUM
    Honua Kai Hokulani 841

    Honua Kai Hokulani 841

    Kaanapali, HI

    This large two bedroom/two bath condo in the hokulani interior courtyard is the perfect vacation spot. With 1320 sq ft of interior living space and an over sized 340 sq ft wraparound lanai, HOKULANI 841 is one of the largest two bedroom condos at...

    Pool Hot Tub
    FREE CANCELLATION

    $595 to $1,973/night

  29. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $583 to $1,861/night

  30. VILLA
    Lele Hideaway

    Lele Hideaway

    Kihei, HI

    Lele Hideaway is a three bedroom, 3 bath two-level condominium suite. Two bedrooms each have a full bathroom and are located on the ground floor. The third bedroom is located below ground level, down a spiral staircase from the living room. The...

    Pool Hot Tub

    $579 to $984/night