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
    Wailea Elua Unit #1204

    Wailea Elua Unit #1204

    Wailea, HI

    Notes from the Owners: Wailea Elua Village #1204 is a beautiful two bedroom, two bath oceanfront condo that has been fully remodeled with top of the line appliances and the latest in furnishings. The large travertine flooring in the kitchen, dining,...

    Pool

    $785 to $1,347/night

  2. 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

    $781 to $1,219/night

  3. 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

    $781 to $1,219/night

  4. 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

    $781 to $1,219/night

  5. 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

    $781 to $1,219/night

  6. 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

    $781 to $1,219/night

  7. 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

  8. 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 $2,153/night

  9. CONDOMINIUM
    Makena Surf Resort, #B-204

    Makena Surf Resort, #B-204

    Makena, HI

    A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second...

    Pool

    $773 to $1,319/night

  10. CONDOMINIUM
    Makena Surf Resort Unit #B-304

    Makena Surf Resort Unit #B-304

    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

    $773 to $1,319/night

  11. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass open to lanai & main living area making this an ideal Hawaiian indoor/outdoor living experience. Elegant...

    Pool Hot Tub

    $766 to $846/night

  12. 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 $934/night

  13. 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...

    Pool

    $750 to $1,699/night

  14. 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 $1,500/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

    $743 to $2,609/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

    $743 to $2,609/night

  17. CONDOMINIUM
    O-1202: Hale Pumehana Ko Olina Beach Villa

    O-1202: Hale Pumehana Ko Olina Beach Villa

    Kapolei, HI

    This 3 BD, 2.5 BA luxury Penthouse on the 12th floor of the Ocean Tower has stunning direct ocean views, was fully re-decorated by a professional interior designer in early 2015 (NEW paint, furnishings, original artwork, built-in closets,...

    Pool

    $740 to $1,668/night

  18. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Direct Ocean Front Cottage where you can watch whales and surfers while relaxing on the large sunning deck, literally hanging over the oceans edge. Features two master suites and private pool, and located just 5 miles from Kailua Village at 78-6658...

    Pool
    FREE CANCELLATION

    $740 to $788/night

  19. 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

    $734 to $3,473/night

  20. CONDOMINIUM
    Makena Surf Resort Unit #f-212

    Makena Surf Resort Unit #f-212

    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

    $729 to $1,094/night

  21. CONDOMINIUM
    Makena Surf Resort, #G-104

    Makena Surf Resort, #G-104

    Kihei, HI

    Makena Surf G-104 is a beautiful, ground floor condo that has a spacious lanai complete with its own BBQ. It opens to perfectly manicured grounds where you can enjoy the lawn and incredible views of the pacific ocean. Makena Surf Resort is a...

    Pool

    $729 to $1,094/night

  22. CONDOMINIUM
    Wailea Elua Unit #0908

    Wailea Elua Unit #0908

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $724 to $1,065/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

    $720 to $1,968/night

  24. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    An upstairs residence at Four Seasons Resort Hualalai, 2901B offers the ultimate in Big Island luxury. With amazing ocean and sunset views, central air conditioning, stylish décor, and use of a golf cart included in every rental, this villa...

    Pool

    $720 to $2,118/night

  25. CONDOMINIUM
    Makena Surf Resort, #G-201

    Makena Surf Resort, #G-201

    Kihei, HI

    akena 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 rocky...

    Pool Hot Tub

    $717 to $1,094/night

  26. CONDOMINIUM
    Wailea Elua Unit #1702

    Wailea Elua Unit #1702

    Wailea, HI

    About this condo: Wailea Elua Village #1702 is a newly remodeled, second floor, two bedroom- two bath condo designed with a living room, dining room and kitchen that openly flow together. New cabinets, granite counter tops, new living room carpet,...

    Pool

    $717 to $1,347/night

  27. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Hale Ili Ili is an oceanfront gated 4 plex.This property is steps from Kamaole Beach #1 and Charley Young's Cove. Panoramic ocean views and magnificent sunsets can be seen daily from this property. This property has an oceanfront pool, hot tub and...

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  28. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani. This gorgeous house is a Brand New Vacation Rental that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION

    $695 to $1,536/night

  29. 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

    $690 to $2,478/night

  30. 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

    $690 to $2,478/night