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. CONDOMINIUM
    1051E Ko Olina Kai Condo

    1051E Ko Olina Kai Condo

    Kapolei, HI

    Want to stay longer? This property sleeps 8* This well maintained 3 Bedroom 2 Bath condo is located in a gated community with resort amenities including a salt water pool, BBQs, Club House, Exercise Room, Putting Green, Tennis Court and a...

    Pool Hot Tub
  2. HOUSE
    Hale O'Pulelehua

    Hale O'Pulelehua

    Hanalei, HI

    Hale O'Pulelehua, 50 Steps to Amazing Banana Beach! TVNC: 1238 A classic plantation style home, this Haena beach house, known as Hale Pulelehu'a (The Butterfly House), is a wonderful place for your family & friends to experience the island...

    $969 to $3800/night

  3. 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

  4. VILLA
    Hualalai Resort Fairway Villa 110C

    Hualalai Resort Fairway Villa 110C

    Kailua Kona, HI

    This garden level 2 bedroom, 2 bath Fairway Villa overlooks the 15th Fairway of the Hualalai Golf Course with views of the ocean beyond. Located within the master-planned resort community of Hualalai, guests have the option of amenity use privileges...

    FREE CANCELLATION

    $934 to $2335/night

  5. HOUSE
    Kolepa Hale

    Kolepa Hale

    koloa, HI

    This fabulous home on the fourth tee of the Kiahuna Plantation Golf Course offers over 2,200 square feet of island luxury, for an unforgettable Kauai getaway. Ideally situated in the exclusive Wainani at Poipu neighborhood, Kolepa Hale includes...

    Pool Hot Tub

    $909 to $1623/night

  6. CONDOMINIUM
    Makena Surf Resort #B-101

    Makena Surf Resort #B-101

    Makena, Maui, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $908 to $1795/night

  7. CONDOMINIUM
    Makena Surf Resort, #G-304

    Makena Surf Resort, #G-304

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $898 to $1235/night

  8. HOUSE
    Hale Poola

    Hale Poola

    Honolulu, HI

    This recently upgraded five bedroom, three bathroom home sits on a small hill in the quiet neighborhood of Aina Haina. Hale Poola comfortably sleeps 10 people, but will house up to 12. The large open living room, media room and kitchen create a nice...

    $896 to $1385/night

  9. 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

  10. 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

  11. VILLA
    Bay Villa 22G2 Gold Ocean Front

    Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Perfectly situated above the waves in the most pristine and highly desired locations in Kapalua! This unique floor plan is the only ground-floor Kapalua Bay villas that can boast an additional 150+ square feet of living space facing the ocean!!...

    Pool

    $881 to $1322/night

  12. 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

  13. 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

  14. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Searching for vacation rentals with a private pool? Look no further because this is one of the best vacation rentals with a private pool on the Big Island. Nestled in an enclosed tropical garden across the way from the Ali’i outdoor marketplace...

    Pool

    $876 to $1284/night

  15. 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

  16. 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

    $860 to $2609/night

  17. 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 $2016/night

  18. 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

  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

    $850 to $2214/night

  20. VILLA
    Bay Villa 30b3 Ocean Front

    Bay Villa 30b3 Ocean Front

    Kapalua, HI

    Relax and rejuvenate. The warm tropical breezes and soothing sounds of the ocean will transport you to a place of total relaxation. Your beautifully UPGRADED KITCHEN with new granite counter tops will beckon you to dine in. After dinner you can curl...

    Pool

    $847 to $1322/night

  21. VILLA
    Bay Villa 21G Gold Beach Front

    Bay Villa 21G Gold Beach Front

    Kapalua, HI

    Stretch out in the spacious comfort of your 2 bedroom 3 bath private villa and take in the warm breezes and magical views that make Kapalua so special. A stately open-air living room provides a full ocean view before opening up to the full panoramic...

    Pool

    $847 to $1322/night

  22. VILLA
    Bay Villa 34b2 Gold Ocean Front

    Bay Villa 34b2 Gold Ocean Front

    Kapalua, HI

    Stunning ocean views from every room! Recent upgrades include new furnishings inside and out, new carpet, fresh paint and accessories. The rugged shore below is home to a variety of tropical birds, exotic plants, fish, and giant sea turtles. During...

    Pool

    $847 to $1322/night

  23. VILLA
    Bay Villa 35B3 Gold Ocean Front

    Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    The spacious interior of this 2 bed 3 bath tranquil retreat is the perfect blend of premium comfort and contemporary modern design. Stately and well-appointed, this lovely villa is uniquely positioned for endless views of the Pacific and neighboring...

    Pool

    $847 to $1322/night

  24. VILLA
    Bay Villa 20G2 Gold Beach Front

    Bay Villa 20G2 Gold Beach Front

    Lahaina, HI

    We invite you to be carried away by this luxury beachfront villa overlooking the azure waters of beautiful Oneloa Bay. Our property is uniquely positioned above the beach in the most desirable location of Kapalua, the crown jewel of West Maui. This...

    Pool

    $847 to $1322/night

  25. HOUSE
    Hale A Kai

    Hale A Kai

    Princeville, HI

    This beautiful custom home is located in the Queen Emma Bluff's gated community in Princeville. The home is approximately 4000 sq feet. Upstairs is a large great room with beautiful hardwood floors. There’s a well equipped gourmet kitchen with a...

    $842 to $1149/night

  26. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Unobstructed Ocean Views from our 9th floor 3 bedroom, 3 bath in Konea Tower with over 1610 sq ft of living space at N. Ka'anapali's newest resort-Honua Kai Resort & Spa. Our vacation rental features 2 Master Suites with lanai access from one of the...

    Pool

    $841 to $2575/night

  27. 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

  28. CONDOMINIUM
    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Bay

    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Ba...

    Kahuku, HI

    This beach level villa has beach and ocean views and is located just steps from the sandy beach with a lawn area before the sand starts. The Ocean Villas pool, jaccuzzi and BBQs are all just 20 yards to your right! It has a serene lanai where you...

    Pool Hot Tub

    $808 to $2478/night

  29. HOUSE
    Plantation Cottage at Kiahuna Village

    Plantation Cottage at Kiahuna Village

    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...

    Pool Hot Tub

    $790 to $2131/night

  30. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Hokulani Villa ~ Simple, Island Luxury Getaway! This newly remodeled Golf Course front home is fresh on the market! This wonderful villa boasts fine furnishings and a very cozy atmosphere. With fantastic views of the golf course, bali hai views and...

    $790 to $2006/night